fix(helm): address PR #447 reviewer feedback

Critical fix:
- deployment.yaml: Only reference OAuth credentials when clientId is set
- Fixes pod failure when using existingSecret without static OAuth creds
- Aligns deployment behavior with secret template logic

Previously, the deployment referenced OAuth credentials when either
clientId OR existingSecret was set. However, the secret template only
includes OAuth credentials when clientId is explicitly provided. This
caused pod failures when users provided an existingSecret for offline
access without static OAuth credentials (intending to use DCR).

The fix ensures OAuth env vars are only referenced when clientId is set,
matching the OAuth mode pattern and allowing DCR to work correctly with
existingSecret configurations.

Minor improvements:
- values.yaml: Clarify OAuth credentials are optional (uses DCR if not provided)

Testing verified all scenarios:
✅ Pass-through only (no offline access): No secrets/PVCs/OAuth vars
✅ Offline + DCR (no clientId): Secret with encryption key only, no OAuth vars
✅ Offline + static OAuth: Secret with all keys, OAuth vars present
✅ existingSecret without clientId: No auto secret, no OAuth vars (FIXED)

Resolves reviewer feedback from PR #447

.github/workflows/appstore-build-publish.yml

@@ -0,0 +1,89 @@
+name: Build and Publish Astrolabe App Release
+
+on:
+  push:
+    tags:
+      - 'astrolabe-v*'
+
+env:
+  APP_NAME: astrolabe
+  APP_DIR: third_party/astrolabe
+
+jobs:
+  build-and-publish:
+    runs-on: ubuntu-latest
+    permissions:
+      contents: write
+
+    steps:
+      - name: Checkout code
+        uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5 # v4
+
+      - name: Get version from tag
+        id: tag
+        run: |
+          echo "TAG=${GITHUB_REF#refs/tags/astrolabe-v}" >> $GITHUB_OUTPUT
+
+      - name: Validate version in info.xml matches tag
+        working-directory: ${{ env.APP_DIR }}
+        run: |
+          INFO_VERSION=$(sed -n 's/.*<version>\(.*\)<\/version>.*/\1/p' appinfo/info.xml | tr -d '\t')
+          if [ "$INFO_VERSION" != "${{ steps.tag.outputs.TAG }}" ]; then
+            echo "Version mismatch: info.xml has $INFO_VERSION but tag is ${{ steps.tag.outputs.TAG }}"
+            exit 1
+          fi
+          echo "Version validated: $INFO_VERSION"
+
+      - name: Setup Node
+        uses: actions/setup-node@49933ea5288caeca8642d1e84afbd3f7d6820020 # v4
+        with:
+          node-version: 22
+
+      - name: Setup PHP
+        uses: shivammathur/setup-php@44454db4f0199b8b9685a5d763dc37cbf79108e1 # v2
+        with:
+          php-version: 8.1
+          coverage: none
+
+      - name: Checkout Nextcloud server (for signing)
+        uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5 # v4
+        with:
+          repository: nextcloud/server
+          ref: stable30
+          path: server
+
+      - name: Install dependencies and build
+        working-directory: ${{ env.APP_DIR }}
+        run: |
+          composer install --no-dev --optimize-autoloader
+          npm ci
+          npm run build
+
+      - name: Setup signing certificate
+        run: |
+          mkdir -p $HOME/.nextcloud/certificates
+          echo "${{ secrets.APP_PRIVATE_KEY }}" > $HOME/.nextcloud/certificates/${{ env.APP_NAME }}.key
+          echo "${{ secrets.APP_PUBLIC_CRT }}" > $HOME/.nextcloud/certificates/${{ env.APP_NAME }}.crt
+
+      - name: Build app store package
+        working-directory: ${{ env.APP_DIR }}
+        run: make appstore server_dir=${{ github.workspace }}/server
+
+      - name: Create GitHub release and attach tarball
+        uses: svenstaro/upload-release-action@6b7fa9f267e90b50a19fef07b3596790bb941741 # v2
+        with:
+          repo_token: ${{ secrets.GITHUB_TOKEN }}
+          file: ${{ env.APP_DIR }}/build/artifacts/${{ env.APP_NAME }}.tar.gz
+          asset_name: ${{ env.APP_NAME }}-${{ steps.tag.outputs.TAG }}.tar.gz
+          tag: ${{ github.ref }}
+          release_name: Astrolabe ${{ steps.tag.outputs.TAG }}
+          prerelease: ${{ contains(steps.tag.outputs.TAG, '-alpha') || contains(steps.tag.outputs.TAG, '-beta') || contains(steps.tag.outputs.TAG, '-rc') }}
+
+      - name: Upload to Nextcloud App Store
+        uses: R0Wi/nextcloud-appstore-push-action@9244bb5445776688cfe90fa1903ea8dff95b0c28 # v1.0.4
+        with:
+          app_name: ${{ env.APP_NAME }}
+          appstore_token: ${{ secrets.APPSTORE_TOKEN }}
+          download_url: ${{ github.server_url }}/${{ github.repository }}/releases/download/${{ github.ref_name }}/${{ env.APP_NAME }}-${{ steps.tag.outputs.TAG }}.tar.gz
+          app_private_key: ${{ secrets.APP_PRIVATE_KEY }}
+          nightly: ${{ contains(steps.tag.outputs.TAG, '-alpha') || contains(steps.tag.outputs.TAG, '-beta') || contains(steps.tag.outputs.TAG, '-rc') }}

.github/workflows/astroglobe-ci.yml

@@ -0,0 +1,275 @@
+# Consolidated CI workflow for Astroglobe Nextcloud app
+#
+# Runs on PRs that modify the astroglobe directory
+# Based on Nextcloud app skeleton workflows
+#
+# SPDX-FileCopyrightText: 2025 Nextcloud MCP Server contributors
+# SPDX-License-Identifier: MIT
+
+name: Astroglobe CI
+
+on:
+  pull_request:
+    paths:
+      - 'third_party/astroglobe/**'
+      - '.github/workflows/astroglobe-ci.yml'
+
+permissions:
+  contents: read
+
+concurrency:
+  group: astroglobe-ci-${{ github.head_ref || github.run_id }}
+  cancel-in-progress: true
+
+jobs:
+  changes:
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+      pull-requests: read
+    outputs:
+      frontend: ${{ steps.changes.outputs.frontend }}
+      php: ${{ steps.changes.outputs.php }}
+    steps:
+      - uses: dorny/paths-filter@de90cc6fb38fc0963ad72b210f1f284cd68cea36 # v3.0.2
+        id: changes
+        continue-on-error: true
+        with:
+          filters: |
+            frontend:
+              - 'third_party/astroglobe/src/**'
+              - 'third_party/astroglobe/package.json'
+              - 'third_party/astroglobe/package-lock.json'
+              - 'third_party/astroglobe/vite.config.js'
+              - 'third_party/astroglobe/**/*.js'
+              - 'third_party/astroglobe/**/*.ts'
+              - 'third_party/astroglobe/**/*.vue'
+            php:
+              - 'third_party/astroglobe/lib/**'
+              - 'third_party/astroglobe/appinfo/**'
+              - 'third_party/astroglobe/composer.json'
+              - 'third_party/astroglobe/psalm.xml'
+
+  # Node.js build and lint
+  node-build:
+    runs-on: ubuntu-latest
+    needs: changes
+    if: needs.changes.outputs.frontend != 'false'
+    name: Node.js build
+    defaults:
+      run:
+        working-directory: third_party/astroglobe
+    steps:
+      - name: Checkout
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
+
+      - name: Read package.json node and npm engines version
+        uses: skjnldsv/read-package-engines-version-actions@06d6baf7d8f41934ab630e97d9e6c0bc9c9ac5e4 # v3
+        id: versions
+        with:
+          path: third_party/astroglobe
+          fallbackNode: '^20'
+          fallbackNpm: '^10'
+
+      - name: Set up node ${{ steps.versions.outputs.nodeVersion }}
+        uses: actions/setup-node@49933ea5288caeca8642d1e84afbd3f7d6820020 # v4.4.0
+        with:
+          node-version: ${{ steps.versions.outputs.nodeVersion }}
+
+      - name: Set up npm ${{ steps.versions.outputs.npmVersion }}
+        run: npm i -g 'npm@${{ steps.versions.outputs.npmVersion }}'
+
+      - name: Install dependencies & build
+        env:
+          CYPRESS_INSTALL_BINARY: 0
+          PUPPETEER_SKIP_DOWNLOAD: true
+        run: |
+          npm ci
+          npm run build --if-present
+
+      - name: Check webpack build changes
+        run: |
+          bash -c "[[ ! \"`git status --porcelain `\" ]] || (echo 'Please recompile and commit the assets' && exit 1)"
+
+  # ESLint
+  eslint:
+    runs-on: ubuntu-latest
+    needs: changes
+    if: needs.changes.outputs.frontend != 'false'
+    name: ESLint
+    defaults:
+      run:
+        working-directory: third_party/astroglobe
+    steps:
+      - name: Checkout
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
+
+      - name: Read package.json node and npm engines version
+        uses: skjnldsv/read-package-engines-version-actions@06d6baf7d8f41934ab630e97d9e6c0bc9c9ac5e4 # v3
+        id: versions
+        with:
+          path: third_party/astroglobe
+          fallbackNode: '^20'
+          fallbackNpm: '^10'
+
+      - name: Set up node ${{ steps.versions.outputs.nodeVersion }}
+        uses: actions/setup-node@49933ea5288caeca8642d1e84afbd3f7d6820020 # v4.4.0
+        with:
+          node-version: ${{ steps.versions.outputs.nodeVersion }}
+
+      - name: Set up npm ${{ steps.versions.outputs.npmVersion }}
+        run: npm i -g 'npm@${{ steps.versions.outputs.npmVersion }}'
+
+      - name: Install dependencies
+        env:
+          CYPRESS_INSTALL_BINARY: 0
+          PUPPETEER_SKIP_DOWNLOAD: true
+        run: npm ci
+
+      - name: Lint
+        run: npm run lint
+
+  # Stylelint
+  stylelint:
+    runs-on: ubuntu-latest
+    needs: changes
+    if: needs.changes.outputs.frontend != 'false'
+    name: Stylelint
+    defaults:
+      run:
+        working-directory: third_party/astroglobe
+    steps:
+      - name: Checkout
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
+
+      - name: Read package.json node and npm engines version
+        uses: skjnldsv/read-package-engines-version-actions@06d6baf7d8f41934ab630e97d9e6c0bc9c9ac5e4 # v3
+        id: versions
+        with:
+          path: third_party/astroglobe
+          fallbackNode: '^20'
+          fallbackNpm: '^10'
+
+      - name: Set up node ${{ steps.versions.outputs.nodeVersion }}
+        uses: actions/setup-node@49933ea5288caeca8642d1e84afbd3f7d6820020 # v4.4.0
+        with:
+          node-version: ${{ steps.versions.outputs.nodeVersion }}
+
+      - name: Set up npm ${{ steps.versions.outputs.npmVersion }}
+        run: npm i -g 'npm@${{ steps.versions.outputs.npmVersion }}'
+
+      - name: Install dependencies
+        env:
+          CYPRESS_INSTALL_BINARY: 0
+          PUPPETEER_SKIP_DOWNLOAD: true
+        run: npm ci
+
+      - name: Lint
+        run: npm run stylelint
+
+  # PHP Code Style
+  php-cs:
+    runs-on: ubuntu-latest
+    needs: changes
+    if: needs.changes.outputs.php != 'false'
+    name: PHP CS Fixer
+    defaults:
+      run:
+        working-directory: third_party/astroglobe
+    steps:
+      - name: Checkout
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
+
+      - name: Get php version
+        id: versions
+        uses: icewind1991/nextcloud-version-matrix@58becf3b4bb6dc6cef677b15e2fd8e7d48c0908f # v1.3.1
+        with:
+          filename: third_party/astroglobe/appinfo/info.xml
+
+      - name: Set up php${{ steps.versions.outputs.php-min }}
+        uses: shivammathur/setup-php@cf4cade2721270509d5b1c766ab3549210a39a2a # v2.33.0
+        with:
+          php-version: ${{ steps.versions.outputs.php-min }}
+          extensions: bz2, ctype, curl, dom, fileinfo, gd, iconv, intl, json, libxml, mbstring, openssl, pcntl, posix, session, simplexml, xmlreader, xmlwriter, zip, zlib, sqlite, pdo_sqlite
+          coverage: none
+          ini-file: development
+        env:
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+
+      - name: Install dependencies
+        run: |
+          composer remove nextcloud/ocp --dev || true
+          composer i
+
+      - name: Lint
+        run: composer run cs:check || ( echo 'Please run `composer run cs:fix` to format your code' && exit 1 )
+
+  # Psalm Static Analysis
+  psalm:
+    runs-on: ubuntu-latest
+    needs: changes
+    if: needs.changes.outputs.php != 'false'
+    name: Psalm
+    defaults:
+      run:
+        working-directory: third_party/astroglobe
+    steps:
+      - name: Checkout
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
+
+      - name: Get php version
+        id: versions
+        uses: icewind1991/nextcloud-version-matrix@58becf3b4bb6dc6cef677b15e2fd8e7d48c0908f # v1.3.1
+        with:
+          filename: third_party/astroglobe/appinfo/info.xml
+
+      - name: Set up php${{ steps.versions.outputs.php-min }}
+        uses: shivammathur/setup-php@cf4cade2721270509d5b1c766ab3549210a39a2a # v2.33.0
+        with:
+          php-version: ${{ steps.versions.outputs.php-min }}
+          extensions: bz2, ctype, curl, dom, fileinfo, gd, iconv, intl, json, libxml, mbstring, openssl, pcntl, posix, session, simplexml, xmlreader, xmlwriter, zip, zlib, sqlite, pdo_sqlite
+          coverage: none
+          ini-file: development
+        env:
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+
+      - name: Install dependencies
+        run: |
+          composer remove nextcloud/ocp --dev || true
+          composer i
+
+      - name: Get OCP version matrix
+        id: ocp-versions
+        uses: icewind1991/nextcloud-version-matrix@58becf3b4bb6dc6cef677b15e2fd8e7d48c0908f # v1.3.1
+        with:
+          filename: third_party/astroglobe/appinfo/info.xml
+
+      - name: Install OCP for static analysis
+        run: |
+          # Get first OCP version from matrix
+          OCP_VERSION=$(echo '${{ steps.ocp-versions.outputs.ocp-matrix }}' | jq -r '.include[0]."ocp-version"')
+          composer require --dev "nextcloud/ocp:$OCP_VERSION" --ignore-platform-reqs --with-dependencies
+
+      - name: Run Psalm
+        run: composer run psalm -- --threads=1 --monochrome --no-progress --output-format=github
+
+  # Summary job
+  summary:
+    permissions:
+      contents: none
+    runs-on: ubuntu-latest
+    needs: [changes, node-build, eslint, stylelint, php-cs, psalm]
+    if: always()
+    name: astroglobe-ci-summary
+    steps:
+      - name: Summary status
+        run: |
+          if ${{ needs.changes.outputs.frontend != 'false' && (needs.node-build.result != 'success' || needs.eslint.result != 'success' || needs.stylelint.result != 'success') }}; then
+            echo "Frontend checks failed"
+            exit 1
+          fi
+          if ${{ needs.changes.outputs.php != 'false' && (needs.php-cs.result != 'success' || needs.psalm.result != 'success') }}; then
+            echo "PHP checks failed"
+            exit 1
+          fi
+          echo "All checks passed"

.github/workflows/bump-version.yml

@@ -7,26 +7,159 @@ on:
 
 jobs:
   bump-version:
-    if: "!startsWith(github.event.head_commit.message, 'bump:')"
+    if: "!startsWith(github.event.head_commit.message, 'bump:') && !startsWith(github.event.head_commit.message, 'chore(release):')"
     runs-on: ubuntu-latest
-    name: "Bump version and create changelog with commitizen"
+    name: "Bump version and create changelog for monorepo components"
     permissions:
       contents: write
       packages: write
     steps:
       - name: Check out
-        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
         with:
           fetch-depth: 0
           token: "${{ secrets.PERSONAL_ACCESS_TOKEN }}"
-      - name: Create bump and changelog
+
-        uses: commitizen-tools/commitizen-action@bb4f1df6601e2a1a891506581b0c53acdc88e07d # 0.26.0
+      - name: Set up Python
+        uses: actions/setup-python@a26af69be951a213d495a4c3e4e4022e16d87065 # v5
         with:
-          github_token: ${{ secrets.PERSONAL_ACCESS_TOKEN }}
+          python-version: '3.11'
-          changelog_increment_filename: body.md
+
-      - name: Release
+      - name: Install uv
-        uses: softprops/action-gh-release@5be0e66d93ac7ed76da52eca8bb058f665c3a5fe # v2.4.2
+        run: |
-        with:
+          curl -LsSf https://astral.sh/uv/install.sh | sh
-          body_path: "body.md"
+          echo "$HOME/.cargo/bin" >> $GITHUB_PATH
-          tag_name: v${{ env.REVISION }}
+
-          token: ${{ secrets.GITHUB_TOKEN }}
+      - name: Configure git
+        run: |
+          git config user.name "github-actions[bot]"
+          git config user.email "github-actions[bot]@users.noreply.github.com"
+
+      - name: Detect and bump component versions
+        id: bump
+        run: |
+          set -euo pipefail
+
+          # Track which components were bumped
+          BUMPED_COMPONENTS=""
+
+          # Helper function to check for commits with specific scope since last tag
+          has_commits_since_tag() {
+            local tag_pattern="$1"
+            local scope_pattern="$2"
+
+            # Get the most recent tag matching the pattern
+            local last_tag=$(git tag --sort=-creatordate | grep -E "^${tag_pattern}" | head -n 1 || echo "")
+
+            if [ -z "$last_tag" ]; then
+              # No previous tag, check all commits on master
+              local commit_range="master"
+            else
+              # Check commits since last tag
+              local commit_range="${last_tag}..HEAD"
+            fi
+
+            # Count commits matching the scope pattern
+            local commit_count=$(git log "$commit_range" --oneline --grep="^${scope_pattern}" -E | wc -l)
+
+            if [ "$commit_count" -gt 0 ]; then
+              echo "Found $commit_count commits for scope '$scope_pattern' since $last_tag"
+              return 0
+            else
+              echo "No commits found for scope '$scope_pattern' since $last_tag"
+              return 1
+            fi
+          }
+
+          # Bump MCP server (default - all commits except helm/astrolabe scopes)
+          echo "Checking MCP server for version bump..."
+
+          # Get the most recent MCP tag
+          last_mcp_tag=$(git tag --sort=-creatordate | grep -E "^v[0-9]" | head -n 1 || echo "")
+
+          if [ -z "$last_mcp_tag" ]; then
+            commit_range="master"
+          else
+            commit_range="${last_mcp_tag}..HEAD"
+          fi
+
+          # Count conventional commits that are NOT scoped to helm or astrolabe
+          mcp_commit_count=$(git log "$commit_range" --oneline --grep="^(feat|fix|docs|refactor|perf|test|build|ci|chore)" -E | \
+            { grep -v "(helm)" || true; } | { grep -v "(astrolabe)" || true; } | wc -l)
+
+          if [ "$mcp_commit_count" -gt 0 ]; then
+            echo "Found $mcp_commit_count commits for MCP server since $last_mcp_tag"
+            echo "Bumping MCP server version..."
+            ./scripts/bump-mcp.sh
+            BUMPED_COMPONENTS="$BUMPED_COMPONENTS mcp"
+          else
+            echo "No commits found for MCP server since $last_mcp_tag"
+          fi
+
+          # Bump Helm chart (scope: helm)
+          echo "Checking Helm chart for version bump..."
+          if has_commits_since_tag "nextcloud-mcp-server-" "(feat|fix|docs|refactor|perf|test|build|ci|chore)\(helm\)(!)?:"; then
+            echo "Bumping Helm chart version..."
+            ./scripts/bump-helm.sh
+            BUMPED_COMPONENTS="$BUMPED_COMPONENTS helm"
+          fi
+
+          # Bump Astrolabe (scope: astrolabe)
+          echo "Checking Astrolabe for version bump..."
+          if has_commits_since_tag "astrolabe-v" "(feat|fix|docs|refactor|perf|test|build|ci|chore)\(astrolabe\)(!)?:"; then
+            echo "Bumping Astrolabe version..."
+            ./scripts/bump-astrolabe.sh
+            BUMPED_COMPONENTS="$BUMPED_COMPONENTS astrolabe"
+          fi
+
+          # Output summary
+          if [ -z "$BUMPED_COMPONENTS" ]; then
+            echo "No components required version bumps"
+            echo "bumped=false" >> $GITHUB_OUTPUT
+          else
+            echo "Bumped components:$BUMPED_COMPONENTS"
+            echo "bumped=true" >> $GITHUB_OUTPUT
+            echo "components=$BUMPED_COMPONENTS" >> $GITHUB_OUTPUT
+          fi
+
+      - name: Push tags
+        if: steps.bump.outputs.bumped == 'true'
+        run: |
+          git push
+          git push --tags
+          echo "Pushed tags for components:${{ steps.bump.outputs.components }}"
+
+      - name: Summary
+        run: |
+          if [ "${{ steps.bump.outputs.bumped }}" == "true" ]; then
+            echo "## Version Bump Summary" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "The following components were bumped:" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+
+            for component in ${{ steps.bump.outputs.components }}; do
+              case $component in
+                mcp)
+                  tag=$(git tag --sort=-creatordate | grep -E '^v[0-9]' | head -n 1)
+                  echo "- **MCP Server**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
+                  ;;
+                helm)
+                  tag=$(git tag --sort=-creatordate | grep -E '^nextcloud-mcp-server-' | head -n 1)
+                  echo "- **Helm Chart**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
+                  ;;
+                astrolabe)
+                  tag=$(git tag --sort=-creatordate | grep -E '^astrolabe-v' | head -n 1)
+                  echo "- **Astrolabe**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
+                  ;;
+              esac
+            done
+
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "Tags have been pushed and release workflows will trigger automatically." >> $GITHUB_STEP_SUMMARY
+          else
+            echo "## Version Bump Summary" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "✅ No version bumps required - no relevant commits found since last release." >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "The workflow completed successfully with no changes." >> $GITHUB_STEP_SUMMARY
+          fi

.github/workflows/claude-code-review.yml

@@ -0,0 +1,57 @@
+name: Claude Code Review
+
+on:
+  pull_request:
+    types: [opened, synchronize]
+    # Optional: Only run on specific file changes
+    # paths:
+    #   - "src/**/*.ts"
+    #   - "src/**/*.tsx"
+    #   - "src/**/*.js"
+    #   - "src/**/*.jsx"
+
+jobs:
+  claude-review:
+    # Optional: Filter by PR author
+    # if: |
+    #   github.event.pull_request.user.login == 'external-contributor' ||
+    #   github.event.pull_request.user.login == 'new-developer' ||
+    #   github.event.pull_request.author_association == 'FIRST_TIME_CONTRIBUTOR'
+
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+      pull-requests: read
+      issues: read
+      id-token: write
+
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        with:
+          fetch-depth: 1
+
+      - name: Run Claude Code Review
+        id: claude-review
+        uses: anthropics/claude-code-action@d7b6d50442a89f005016e778bf825a72ef582525 # v1
+        with:
+          claude_code_oauth_token: ${{ secrets.CLAUDE_CODE_OAUTH_TOKEN }}
+          prompt: |
+            REPO: ${{ github.repository }}
+            PR NUMBER: ${{ github.event.pull_request.number }}
+
+            Please review this pull request and provide feedback on:
+            - Code quality and best practices
+            - Potential bugs or issues
+            - Performance considerations
+            - Security concerns
+            - Test coverage
+
+            Use the repository's CLAUDE.md for guidance on style and conventions. Be constructive and helpful in your feedback.
+
+            Use `gh pr comment` with your Bash tool to leave your review as a comment on the PR.
+
+          # See https://github.com/anthropics/claude-code-action/blob/main/docs/usage.md
+          # or https://docs.claude.com/en/docs/claude-code/cli-reference for available options
+          claude_args: '--allowed-tools "Bash(gh issue view:*),Bash(gh search:*),Bash(gh issue list:*),Bash(gh pr comment:*),Bash(gh pr diff:*),Bash(gh pr view:*),Bash(gh pr list:*)"'
+

.github/workflows/claude.yml

@@ -0,0 +1,50 @@
+name: Claude Code
+
+on:
+  issue_comment:
+    types: [created]
+  pull_request_review_comment:
+    types: [created]
+  issues:
+    types: [opened, assigned]
+  pull_request_review:
+    types: [submitted]
+
+jobs:
+  claude:
+    if: |
+      (github.event_name == 'issue_comment' && contains(github.event.comment.body, '@claude')) ||
+      (github.event_name == 'pull_request_review_comment' && contains(github.event.comment.body, '@claude')) ||
+      (github.event_name == 'pull_request_review' && contains(github.event.review.body, '@claude')) ||
+      (github.event_name == 'issues' && (contains(github.event.issue.body, '@claude') || contains(github.event.issue.title, '@claude')))
+    runs-on: ubuntu-latest
+    permissions:
+      contents: read
+      pull-requests: read
+      issues: read
+      id-token: write
+      actions: read # Required for Claude to read CI results on PRs
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        with:
+          fetch-depth: 1
+
+      - name: Run Claude Code
+        id: claude
+        uses: anthropics/claude-code-action@d7b6d50442a89f005016e778bf825a72ef582525 # v1
+        with:
+          claude_code_oauth_token: ${{ secrets.CLAUDE_CODE_OAUTH_TOKEN }}
+
+          # This is an optional setting that allows Claude to read CI results on PRs
+          additional_permissions: |
+            actions: read
+
+          # Optional: Give a custom prompt to Claude. If this is not specified, Claude will perform the instructions specified in the comment that tagged it.
+          # prompt: 'Update the pull request description to include a summary of changes.'
+
+          # Optional: Add claude_args to customize behavior and configuration
+          # See https://github.com/anthropics/claude-code-action/blob/main/docs/usage.md
+          # or https://docs.claude.com/en/docs/claude-code/cli-reference for available options
+          # claude_args: '--allowed-tools Bash(gh pr:*)'
+

.github/workflows/docker-build-publish.yml

@@ -2,7 +2,8 @@ name: Build and Publish Docker Image
 
 on:
   push:
-    tags: ["*"]
+    tags:
+      - "v*"
 
 jobs:
   build-and-push:
@@ -12,11 +13,11 @@ jobs:
       packages: write
     steps:
       - name: Checkout repository
-        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
 
       - name: Docker meta
         id: meta
-        uses: docker/metadata-action@318604b99e75e41977312d83839a89be02ca4893 # v5
+        uses: docker/metadata-action@c299e40c65443455700f0fdfc63efafe5b349051 # v5
         with:
           # list of Docker images to use as base name for tags
           images: |
@@ -33,7 +34,7 @@ jobs:
             type=raw,value=latest,enable={{is_default_branch}}
 
       - name: Set up Docker Buildx
-        uses: docker/setup-buildx-action@e468171a9de216ec08956ac3ada2f0791b6bd435 # v3
+        uses: docker/setup-buildx-action@8d2750c68a42422c14e847fe6c8ac0403b4cbd6f # v3
 
       - name: Log in to GitHub Container Registry
         if: github.event_name != 'pull_request'

.github/workflows/helm-release.yml

@@ -14,7 +14,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Checkout
-        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
         with:
           fetch-depth: 0
 
@@ -38,6 +38,8 @@ jobs:
 
       - name: Run chart-releaser
         uses: helm/chart-releaser-action@cae68fefc6b5f367a0275617c9f83181ba54714f # v1.7.0
+        with:
+          skip_existing: true
         env:
           CR_TOKEN: "${{ secrets.GITHUB_TOKEN }}"
 

.github/workflows/rag-evaluation.yml

@@ -24,39 +24,25 @@ jobs:
       models: read
 
     steps:
-      - uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
+      - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
-        with:
-          submodules: 'true'
-
-      ###### Required to build OIDC App ######
-      - name: Set up php 8.4
-        uses: shivammathur/setup-php@bf6b4fbd49ca58e4608c9c89fba0b8d90bd2a39f # v2
-        with:
-          php-version: 8.4
-          coverage: none
-
-      - name: Install OIDC app composer dependencies
-        run: |
-          cd third_party/oidc
-          composer install --no-dev
-      ###### Required to build OIDC App ######
 
       - name: Run docker compose with vector sync
-        uses: hoverkraft-tech/compose-action@3846bcd61da338e9eaaf83e7ed0234a12b099b72 # v2.4.1
+        uses: hoverkraft-tech/compose-action@248470ecc5ed40d8ed3d4480d8260d77179ef579 # v2.4.2
         with:
-          compose-file: "./docker-compose.yml"
+          compose-file: |
+            ./docker-compose.yml
+            ./docker-compose.ci.yml
           up-flags: "--build"
         env:
-          # Override MCP container environment for OpenAI + vector sync
+          # Environment variables passed to docker-compose.ci.yml
-          VECTOR_SYNC_ENABLED: "true"
-          VECTOR_SYNC_SCAN_INTERVAL: "5"
           OPENAI_API_KEY: ${{ secrets.GITHUB_TOKEN }}
           OPENAI_BASE_URL: "https://models.github.ai/inference"
           OPENAI_EMBEDDING_MODEL: ${{ inputs.embedding_model }}
           OPENAI_GENERATION_MODEL: ${{ inputs.generation_model }}
+          VECTOR_SYNC_SCAN_INTERVAL: "5"
 
       - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@1e862dfacbd1d6d858c55d9b792c756523627244 # v7.1.4
+        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
 
       - name: Wait for Nextcloud to be ready
         run: |
@@ -101,11 +87,17 @@ jobs:
           OPENAI_EMBEDDING_MODEL: ${{ inputs.embedding_model }}
           OPENAI_GENERATION_MODEL: ${{ inputs.generation_model }}
         run: |
-          uv run pytest tests/integration/test_rag_openai.py -v --log-cli-level=INFO
+          uv run pytest tests/integration/test_rag.py -v --log-cli-level=INFO --provider openai
+
+      - name: Capture MCP container logs
+        if: always()
+        run: |
+          echo "=== MCP Container Logs ==="
+          docker compose logs mcp --tail=500
 
       - name: Upload test results
         if: always()
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5
         with:
           name: rag-evaluation-results
           path: |

.github/workflows/release.yml

@@ -18,9 +18,9 @@ jobs:
       contents: read
     steps:
       - name: Checkout
-        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6
+        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
       - name: Install uv
-        uses: astral-sh/setup-uv@1e862dfacbd1d6d858c55d9b792c756523627244 # v7.1.4
+        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
       - name: Install Python 3.11
         run: uv python install 3.11
       - name: Build

.github/workflows/test.yml

@@ -9,9 +9,9 @@ jobs:
   linting:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
+      - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
       - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@1e862dfacbd1d6d858c55d9b792c756523627244 # v7.1.4
+        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
       - name: Check format
         run: |
           uv run --frozen ruff format --diff
@@ -27,7 +27,7 @@ jobs:
     runs-on: ubuntu-latest
 
     steps:
-      - uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
+      - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
         with:
           submodules: 'true'
 
@@ -35,7 +35,7 @@ jobs:
       ###### Required to build OIDC App ######
 
       - name: Set up php 8.4
-        uses: shivammathur/setup-php@bf6b4fbd49ca58e4608c9c89fba0b8d90bd2a39f # v2
+        uses: shivammathur/setup-php@44454db4f0199b8b9685a5d763dc37cbf79108e1 # v2
         with:
           php-version: 8.4
           coverage: none
@@ -48,15 +48,32 @@ jobs:
       ###### Required to build OIDC App ######
 
 
+      ###### Required to build Astrolabe App ######
+
+      - name: Set up Node.js for Astrolabe
+        uses: actions/setup-node@39370e3970a6d050c480ffad4ff0ed4d3fdee5af # v4.1.0
+        with:
+          node-version: '20'
+
+      - name: Build Astrolabe app
+        run: |
+          cd third_party/astrolabe
+          composer install --no-dev --optimize-autoloader
+          npm ci
+          npm run build
+
+      ###### Required to build Astrolabe App ######
+
+
       - name: Run docker compose
-        uses: hoverkraft-tech/compose-action@3846bcd61da338e9eaaf83e7ed0234a12b099b72 # v2.4.1
+        uses: hoverkraft-tech/compose-action@248470ecc5ed40d8ed3d4480d8260d77179ef579 # v2.4.2
         with:
           compose-file: "./docker-compose.yml"
           #compose-flags: "--profile qdrant"
           up-flags: "--build"
 
       - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@1e862dfacbd1d6d858c55d9b792c756523627244 # v7.1.4
+        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
 
       - name: Install Playwright dependencies
         run: |

CHANGELOG.md

@@ -1,3 +1,222 @@
+# Changelog - MCP Server
+
+All notable changes to the Nextcloud MCP Server will be documented in this file.
+
+The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
+and this project adheres to [PEP 440](https://peps.python.org/pep-0440/).
+
+## v0.57.0 (2025-12-20)
+
+### Feat
+
+- **auth**: add multi-user BasicAuth pass-through mode
+- **astrolabe**: add dynamic MCP server configuration for testing
+
+### Fix
+
+- **config**: address reviewer feedback
+
+### Refactor
+
+- **config**: centralize configuration validation and simplify startup
+
+## v0.56.2 (2025-12-20)
+
+### Fix
+
+- **astrolabe**: screenshots in info.xml
+- **astrolabe**: screenshots in info.xml
+
+## v0.56.1 (2025-12-19)
+
+### Fix
+
+- **astrolabe**: Update screenshots
+- **ci**: skip existing Helm chart releases to prevent duplicate release errors
+
+## v0.56.0 (2025-12-19)
+
+### Feat
+
+- **ci**: add --increment flag to bump scripts for manual version control
+
+### Fix
+
+- **astrolabe**: add contents:write permission to appstore workflow
+- **astrolabe**: update commitizen pattern to properly update info.xml version
+- **astrolabe**: prevent workflow failure when only helm/astrolabe commits exist
+- **astrolabe**: info.xml
+
+## v0.55.1 (2025-12-19)
+
+### Fix
+
+- **ci**: push all tags explicitly in bump workflow
+
+## v0.55.0 (2025-12-19)
+
+### BREAKING CHANGE
+
+- MCP server now bumps for ANY conventional commit except
+those explicitly scoped to helm or astrolabe.
+
+### Feat
+
+- **ci**: implement monorepo-aware version bumping workflow
+
+### Fix
+
+- **ci**: make MCP server default bump target for all non-scoped commits
+- **ci**: restrict docker build to MCP server tags only
+- **ci**: correct appstore-push-action version to v1.0.4
+
+## v0.54.0 (2025-12-19)
+
+### Feat
+
+- **astrolabe**: add Nextcloud App Store deployment automation
+- configure commitizen monorepo with independent versioning
+
+### Fix
+
+- **ci**: improve versioning and error handling
+- **ci**: address critical workflow and validation issues
+- **astrolabe**: address code review feedback
+
+## v0.53.0 (2025-12-19)
+
+### Feat
+
+- add Alembic database migration system
+- make chunk modal title clickable link to documents
+- add native Plotly hover styling for clickable points
+- add click interactivity to Plotly 3D scatter chart
+- improve chunk viewer with fixed navigation and markdown rendering
+- **astrolabe**: enable multi-select for document types and refactor PDF viewer
+- **auth**: implement refresh token rotation for Nextcloud OIDC
+- **astrolabe**: enhance unified search and add webhook management
+- **astrolabe**: add webhook management UI to admin settings
+- **astrolabe**: add OAuth token refresh and webhook presets
+- **search**: add file_path metadata and chunk offsets to search results
+- **astrolabe**: use proper icons and thumbnails in unified search
+- **astrolabe**: add admin search settings and enhanced UI
+- **astrolabe**: add unified search provider with clickable file links
+- **astrolabe**: add 3D PCA visualization for semantic search
+- **astrolabe**: add Nextcloud PHP app for MCP server management
+- **vector-sync**: enable background sync in OAuth mode
+
+### Fix
+
+- **security**: address critical security issues from PR #401 code review
+- **oauth**: enable PKCE for all clients and add token_broker to oauth_context
+- **astrolabe**: revert invalid files_pdfviewer URL for file links
+- resolve type checking warnings for CI
+- move Alembic to package submodule for Docker compatibility
+- update unified search results to match chunk viz display
+- **astrolabe**: handle OAuth refresh token rotation
+- address critical code review issues (4 fixes)
+- resolve CI linting issues for Astroglobe
+
+### Refactor
+
+- **astrolabe**: extract PDF viewer to dedicated component
+- **astrolabe**: reframe UI as semantic search service
+
+## v0.52.1 (2025-12-13)
+
+### Perf
+
+- **deck**: optimize card lookup by storing board_id/stack_id in metadata
+
+## v0.52.0 (2025-12-13)
+
+### Feat
+
+- **vector**: add Deck card vector search with visualization support
+
+## v0.51.0 (2025-12-13)
+
+### Feat
+
+- **vector-viz**: add news_item support for links and chunk expansion
+
+## v0.50.2 (2025-12-13)
+
+### Fix
+
+- **news**: revert get_item() to use get_items() + filter
+
+## v0.50.1 (2025-12-12)
+
+### Fix
+
+- Disable DNS rebinding protection for containerized deployments
+- **deps**: update dependency mcp to >=1.23,<1.24
+
+## v0.50.0 (2025-12-11)
+
+### Feat
+
+- add MCP tool annotations for enhanced UX
+
+### Fix
+
+- address PR review feedback
+
+## v0.49.2 (2025-12-09)
+
+### Fix
+
+- Update lockfile
+
+## v0.49.1 (2025-12-09)
+
+### Fix
+
+- Revert mcp version <1.23
+
+## v0.49.0 (2025-12-08)
+
+### Feat
+
+- **news**: add Nextcloud News app integration
+
+### Fix
+
+- resolve all type checking errors (8 errors fixed)
+
+### Refactor
+
+- **news**: simplify vector sync to fetch all items
+
+### Perf
+
+- **news**: use direct API endpoint for get_item()
+
+## v0.48.6 (2025-12-03)
+
+### Fix
+
+- **deps**: update dependency mcp to >=1.23,<1.24
+
+## v0.48.5 (2025-11-28)
+
+### Fix
+
+- **deps**: update dependency pillow to v12
+
+## v0.48.4 (2025-11-23)
+
+### Fix
+
+- Add rate limit retry logic to OpenAI provider
+
+## v0.48.3 (2025-11-23)
+
+### Fix
+
+- Increase MCP sampling timeout to 5 minutes for slower LLMs
+
 ## v0.48.2 (2025-11-23)
 
 ### Fix

CLAUDE.md

@@ -56,6 +56,68 @@ This file provides guidance to Claude Code (claude.ai/code) when working with co
   - Pass-through (default): Simple, stateless (ENABLE_TOKEN_EXCHANGE=false)
   - Token exchange (opt-in): RFC 8693 delegation (ENABLE_TOKEN_EXCHANGE=true)
 
+### MCP Tool Annotations (ADR-017)
+
+**All tools MUST include annotations** following these patterns:
+
+```python
+from mcp.types import ToolAnnotations
+
+# Read-only tools (list, search, get)
+@mcp.tool(
+    title="Human Readable Name",
+    annotations=ToolAnnotations(
+        readOnlyHint=True,
+        openWorldHint=True,  # Nextcloud is external to MCP server
+    ),
+)
+
+# Create operations
+@mcp.tool(
+    title="Create Resource",
+    annotations=ToolAnnotations(
+        idempotentHint=False,  # Creates new resources each time
+        openWorldHint=True,
+    ),
+)
+
+# Update operations (with etag/version control)
+@mcp.tool(
+    title="Update Resource",
+    annotations=ToolAnnotations(
+        idempotentHint=False,  # ETag changes = different inputs
+        openWorldHint=True,
+    ),
+)
+
+# Delete operations
+@mcp.tool(
+    title="Delete Resource",
+    annotations=ToolAnnotations(
+        destructiveHint=True,   # Permanently deletes data
+        idempotentHint=True,    # Same end state if called repeatedly
+        openWorldHint=True,
+    ),
+)
+
+# HTTP PUT without version control (special case)
+@mcp.tool(
+    title="Write File",
+    annotations=ToolAnnotations(
+        idempotentHint=True,  # Same content = same end state
+        openWorldHint=True,
+    ),
+)
+```
+
+**Key Principles**:
+- **Idempotency**: Same inputs → same result. ETags change after updates, making them non-idempotent
+- **Destructive**: Operations that permanently delete/overwrite data
+- **Open World**: All Nextcloud tools access external service (openWorldHint=True)
+- **Titles**: Use human-readable names, not snake_case function names
+
+**See**: `docs/ADR-017-mcp-tool-annotations.md` for detailed rationale and examples
+
 ### Project Structure
 - `nextcloud_mcp_server/client/` - HTTP clients for Nextcloud APIs
 - `nextcloud_mcp_server/server/` - MCP tool/resource definitions
@@ -444,6 +506,29 @@ docker compose exec app php occ user_oidc:provider keycloak
 **Nextcloud**: `docker compose exec app php occ ...` for occ commands
 **MariaDB**: `docker compose exec db mariadb -u [user] -p [password] [database]` for queries
 
+### Querying Nextcloud Application Logs
+
+**Use this pattern** to inspect Nextcloud application logs during debugging:
+
+```bash
+# View recent log entries
+docker compose exec app cat /var/www/html/data/nextcloud.log | jq | tail
+
+# Filter by app
+docker compose exec app cat /var/www/html/data/nextcloud.log | jq 'select(.app == "astrolabe")' | tail
+
+# Filter by log level (0=DEBUG, 1=INFO, 2=WARN, 3=ERROR, 4=FATAL)
+docker compose exec app cat /var/www/html/data/nextcloud.log | jq 'select(.level >= 3)' | tail
+
+# Search for specific messages
+docker compose exec app cat /var/www/html/data/nextcloud.log | jq 'select(.message | contains("OAuth"))' | tail -20
+
+# View full exception traces
+docker compose exec app cat /var/www/html/data/nextcloud.log | jq 'select(.exception != null)' | tail -5
+```
+
+**Log Structure**: Each entry is a JSON object with fields: `reqId`, `level`, `time`, `remoteAddr`, `user`, `app`, `method`, `url`, `message`, `userAgent`, `version`, `exception`
+
 **For detailed setup, see**:
 - `docs/installation.md` - Installation guide
 - `docs/configuration.md` - Configuration options

CONTRIBUTING.md

@@ -0,0 +1,116 @@
+# Contributing to Nextcloud MCP Server
+
+## Version Management
+
+This monorepo uses commitizen for version management with **independent versioning** for three components:
+
+### Components
+
+| Component | Scope | Bump Command | Tag Example |
+|-----------|-------|--------------|-------------|
+| MCP Server | `mcp` or none | `./scripts/bump-mcp.sh` | `v0.54.0` |
+| Helm Chart | `helm` | `./scripts/bump-helm.sh` | `nextcloud-mcp-server-0.54.0` |
+| Astrolabe App | `astrolabe` | `./scripts/bump-astrolabe.sh` | `astrolabe-v0.2.0` |
+
+### Commit Message Format
+
+Use conventional commits with **scopes** to target specific components:
+
+```bash
+# MCP server changes
+feat(mcp): add calendar sync API
+fix(mcp): resolve authentication bug
+
+# Helm chart changes
+feat(helm): add resource limits
+docs(helm): update values documentation
+
+# Astrolabe app changes
+feat(astrolabe): add dark mode toggle
+fix(astrolabe): resolve search UI bug
+```
+
+**Unscoped commits** default to the MCP server:
+```bash
+feat: add new feature  # → MCP server (v0.54.0)
+```
+
+### Release Workflow
+
+#### 1. Make Changes with Scoped Commits
+
+```bash
+git commit -m "feat(astrolabe): add dark mode toggle"
+git commit -m "feat(helm): add ingress annotations"
+git commit -m "feat(mcp): add calendar sync"
+```
+
+#### 2. Bump Component Versions
+
+```bash
+# Bump MCP server (reads commits with scope=mcp or unscoped)
+./scripts/bump-mcp.sh
+# → Creates tag: v0.54.0
+# → Updates: pyproject.toml, Chart.yaml:appVersion
+
+# Bump Helm chart (reads commits with scope=helm)
+./scripts/bump-helm.sh
+# → Creates tag: nextcloud-mcp-server-0.54.0
+# → Updates: Chart.yaml:version
+
+# Bump Astrolabe (reads commits with scope=astrolabe)
+./scripts/bump-astrolabe.sh
+# → Creates tag: astrolabe-v0.2.0
+# → Updates: info.xml, package.json
+```
+
+#### 3. Push Tags
+
+```bash
+git push --follow-tags
+```
+
+### Changelog Filtering
+
+Each component maintains its own `CHANGELOG.md`:
+
+- **MCP Server**: `CHANGELOG.md` (root) - includes `feat(mcp):` and unscoped commits
+- **Helm Chart**: `charts/nextcloud-mcp-server/CHANGELOG.md` - includes `feat(helm):` only
+- **Astrolabe**: `third_party/astrolabe/CHANGELOG.md` - includes `feat(astrolabe):` only
+
+### Manual Version Bumps
+
+For specific increments:
+
+```bash
+# Patch bump (0.53.0 → 0.53.1)
+uv run cz bump --increment PATCH
+
+# Minor bump (0.53.0 → 0.54.0)
+uv run cz bump --increment MINOR
+
+# Major bump (0.53.0 → 1.0.0)
+uv run cz bump --increment MAJOR
+
+# For non-MCP components, use --config
+cd charts/nextcloud-mcp-server
+uv run cz --config .cz.toml bump --increment MINOR
+```
+
+### Versioning Philosophy
+
+- **MCP Server**: Follows PEP 440, `major_version_zero = true` (0.x.x for pre-1.0)
+- **Helm Chart**: Follows PEP 440, starts at 0.53.0 (continues from current)
+- **Astrolabe**: Follows PEP 440, `major_version_zero = true` (0.x.x for alpha/beta)
+
+### Chart.yaml Version vs appVersion
+
+The Helm chart has TWO version fields:
+
+- **`version`**: Chart packaging version (bumped by `feat(helm):`)
+  - Example: `0.53.0` → `0.54.0` when adding resource limits
+
+- **`appVersion`**: MCP server version being deployed (bumped by `feat(mcp):`)
+  - Example: `"0.53.0"` → `"0.54.0"` when MCP server releases
+
+This allows the chart to evolve independently from the application.

Dockerfile

@@ -1,6 +1,6 @@
-FROM docker.io/library/python:3.12-slim-trixie@sha256:b43ff04d5df04ad5cabb80890b7ef74e8410e3395b19af970dcd52d7a4bff921
+FROM docker.io/library/python:3.12-slim-trixie@sha256:fa48eefe2146644c2308b909d6bb7651a768178f84fc9550dcd495e4d6d84d01
 
-COPY --from=ghcr.io/astral-sh/uv:0.9.11@sha256:5aa820129de0a600924f166aec9cb51613b15b68f1dcd2a02f31a500d2ede568 /uv /uvx /bin/
+COPY --from=ghcr.io/astral-sh/uv:0.9.18@sha256:5713fa8217f92b80223bc83aac7db36ec80a84437dbc0d04bbc659cae030d8c9 /uv /uvx /bin/
 
 # Install dependencies
 # 1. git (required for caldav dependency from git)
@@ -12,13 +12,17 @@ RUN apt update && apt install --no-install-recommends --no-install-suggests -y \
 
 WORKDIR /app
 
+COPY pyproject.toml uv.lock README.md .
+
+RUN uv sync --locked --no-dev --no-install-project --no-cache
+
 COPY . .
 
 RUN uv sync --locked --no-dev --no-editable --no-cache
 
 ENV PYTHONUNBUFFERED=1
 ENV VIRTUAL_ENV=/app/.venv
-ENV PATH=/app/.vnev/bin:$PATH
+ENV PATH=/app/.venv/bin:$PATH
 ENV TESSDATA_PREFIX=/usr/share/tesseract-ocr/5/tessdata
 
-ENTRYPOINT ["/app/.venv/bin/nextcloud-mcp-server", "--host", "0.0.0.0"]
+ENTRYPOINT ["/app/.venv/bin/nextcloud-mcp-server", "run", "--host", "0.0.0.0"]

Dockerfile.smithery

@@ -12,12 +12,12 @@
 # - Per-session app password authentication
 # - Multi-user support via Smithery session config
 
-FROM docker.io/library/python:3.12-slim-trixie@sha256:b43ff04d5df04ad5cabb80890b7ef74e8410e3395b19af970dcd52d7a4bff921
+FROM docker.io/library/python:3.12-slim-trixie@sha256:fa48eefe2146644c2308b909d6bb7651a768178f84fc9550dcd495e4d6d84d01
 
 WORKDIR /app
 
 # Install uv for fast dependency management
-COPY --from=ghcr.io/astral-sh/uv:0.9.11@sha256:5aa820129de0a600924f166aec9cb51613b15b68f1dcd2a02f31a500d2ede568 /uv /uvx /bin/
+COPY --from=ghcr.io/astral-sh/uv:0.9.18@sha256:5713fa8217f92b80223bc83aac7db36ec80a84437dbc0d04bbc659cae030d8c9 /uv /uvx /bin/
 
 # Install dependencies
 # 1. git (required for caldav dependency from git)

README.md

@@ -63,7 +63,7 @@ http://127.0.0.1:8000/mcp
 
 - **90+ MCP Tools** - Comprehensive API coverage across 8 Nextcloud apps
 - **MCP Resources** - Structured data URIs for browsing Nextcloud data
-- **Semantic Search (Experimental)** - Optional vector-powered search for Notes (requires Qdrant + Ollama)
+- **Semantic Search (Experimental)** - Optional vector-powered search for Notes, Files, News items, and Deck cards (requires Qdrant + Ollama)
 - **Document Processing** - OCR and text extraction from PDFs, DOCX, images with progress notifications
 - **Flexible Deployment** - Docker, Kubernetes (Helm), VM, or local installation
 - **Production-Ready Auth** - Basic Auth with app passwords (recommended) or OAuth2/OIDC (experimental)
@@ -81,7 +81,7 @@ http://127.0.0.1:8000/mcp
 | **Cookbook** | 13 | Recipe management, URL import (schema.org) |
 | **Tables** | 5 | Row operations on Nextcloud Tables |
 | **Sharing** | 10+ | Create and manage shares |
-| **Semantic Search** | 2+ | Vector search for Notes (experimental, opt-in, requires infrastructure) |
+| **Semantic Search** | 2+ | Vector search for Notes, Files, News items, and Deck cards (experimental, opt-in, requires infrastructure) |
 
 Want to see another Nextcloud app supported? [Open an issue](https://github.com/cbcoutinho/nextcloud-mcp-server/issues) or contribute a pull request!
 
@@ -127,7 +127,7 @@ This enables natural language queries and helps discover related content across
 
 > [!NOTE]
 > **Semantic Search is experimental and opt-in:**
-> - Disabled by default (`VECTOR_SYNC_ENABLED=false`)
+> - Disabled by default (`ENABLE_SEMANTIC_SEARCH=false`)
 > - Currently supports Notes app only (multi-app support planned)
 > - Requires additional infrastructure: vector database + embedding service
 > - Answer generation (`nc_semantic_search_answer`) requires MCP client sampling support
@@ -145,7 +145,7 @@ This enables natural language queries and helps discover related content across
 ### Features
 - **[App Documentation](docs/)** - Notes, Calendar, Contacts, WebDAV, Deck, Cookbook, Tables
 - **[Document Processing](docs/configuration.md#document-processing)** - OCR and text extraction setup
-- **[Semantic Search Architecture](docs/semantic-search-architecture.md)** - Experimental vector search (Notes only, opt-in)
+- **[Semantic Search Architecture](docs/semantic-search-architecture.md)** - Experimental vector search (Notes, Files, News items, Deck cards; opt-in)
 - **[Vector Sync UI Guide](docs/user-guide/vector-sync-ui.md)** - Browser interface for semantic search visualization and testing
 
 ### Advanced Topics

alembic.ini

@@ -0,0 +1,90 @@
+# Alembic configuration file for nextcloud-mcp-server
+
+[alembic]
+# Path to migration scripts
+script_location = nextcloud_mcp_server/alembic
+
+# Template used to generate migration file names
+# Default: %%(rev)s_%%(slug)s
+file_template = %%(year)d%%(month).2d%%(day).2d_%%(hour).2d%%(minute).2d_%%(rev)s_%%(slug)s
+
+# Timezone for migration timestamps
+# Default: utc
+timezone = utc
+
+# Max length of characters to apply to the "slug" field
+# Default: 40
+# truncate_slug_length = 40
+
+# Set to 'true' to run the environment during the 'revision' command
+# Default: false
+# revision_environment = false
+
+# Set to 'true' to allow .pyc and .pyo files without a source .py file
+# Default: false
+# sourceless = false
+
+# Version location specification
+# Supports single or multiple directories
+version_locations = nextcloud_mcp_server/alembic/versions
+
+# Path separator for version locations (required to suppress deprecation warning)
+# Use os (for cross-platform compatibility)
+path_separator = os
+
+# Set to 'true' to search source files recursively in each "version_locations" directory
+# Default: false
+# recursive_version_locations = false
+
+# Output encoding used when revision files are written
+# Default: utf-8
+# output_encoding = utf-8
+
+# Database URL - can be overridden by:
+# 1. Passing -x database_url=... to alembic commands
+# 2. Setting in environment via get_database_url() in env.py
+# Default: sqlite:///app/data/tokens.db
+sqlalchemy.url = sqlite+aiosqlite:////app/data/tokens.db
+
+[post_write_hooks]
+# Post-write hooks allow you to run scripts after generating migration files
+# Example: format migrations with ruff
+# hooks = ruff
+# ruff.type = exec
+# ruff.executable = ruff
+# ruff.options = format REVISION_SCRIPT_FILENAME
+
+# Logging configuration
+[loggers]
+keys = root,sqlalchemy,alembic
+
+[handlers]
+keys = console
+
+[formatters]
+keys = generic
+
+[logger_root]
+level = WARN
+handlers = console
+qualname =
+
+[logger_sqlalchemy]
+level = WARN
+handlers =
+qualname = sqlalchemy.engine
+
+[logger_alembic]
+level = INFO
+handlers =
+qualname = alembic
+
+[handler_console]
+class = StreamHandler
+args = (sys.stderr,)
+level = NOTSET
+formatter = generic
+
+[formatter_generic]
+format = %(levelname)-5.5s [%(name)s] %(message)s
+datefmt = %H:%M:%S

alembic/README

@@ -0,0 +1,71 @@
+Database Migrations for nextcloud-mcp-server
+============================================
+
+This directory contains Alembic database migrations for the token storage database.
+
+Structure
+---------
+- env.py: Alembic environment configuration
+- script.py.mako: Template for generating new migration files
+- versions/: Directory containing migration scripts
+
+Usage
+-----
+Migrations are managed via the CLI:
+
+    # Upgrade database to latest version
+    uv run nextcloud-mcp-server db upgrade
+
+    # Show current database version
+    uv run nextcloud-mcp-server db current
+
+    # Show migration history
+    uv run nextcloud-mcp-server db history
+
+    # Create a new migration (developers only)
+    uv run nextcloud-mcp-server db migrate "description of changes"
+
+    # Downgrade database by one version (emergency use only)
+    uv run nextcloud-mcp-server db downgrade
+
+Direct Alembic Usage
+--------------------
+You can also use Alembic commands directly:
+
+    # Specify database URL via -x flag
+    uv run alembic -x database_url=sqlite+aiosqlite:////path/to/tokens.db upgrade head
+
+    # Or set in alembic.ini and run
+    uv run alembic upgrade head
+    uv run alembic current
+    uv run alembic history
+
+Writing Migrations
+------------------
+Since we don't use SQLAlchemy models, migrations are written with raw SQL:
+
+    def upgrade() -> None:
+        op.execute("""
+            ALTER TABLE refresh_tokens
+            ADD COLUMN new_field TEXT
+        """)
+
+    def downgrade() -> None:
+        # SQLite doesn't support DROP COLUMN, use table recreation
+        op.execute("""
+            CREATE TABLE refresh_tokens_new AS
+            SELECT user_id, encrypted_token, ... FROM refresh_tokens
+        """)
+        op.execute("DROP TABLE refresh_tokens")
+        op.execute("ALTER TABLE refresh_tokens_new RENAME TO refresh_tokens")
+
+Migration File Naming
+---------------------
+Format: YYYYMMDD_HHMM_<revision>_<slug>.py
+Example: 20251217_2200_001_initial_schema.py
+
+Notes
+-----
+- Migrations run automatically when RefreshTokenStorage.initialize() is called
+- Existing databases are automatically stamped with the initial version
+- SQLite has limited ALTER TABLE support - complex changes require table recreation

alembic/script.py.mako

@@ -0,0 +1,26 @@
+"""${message}
+
+Revision ID: ${up_revision}
+Revises: ${down_revision | comma,n}
+Create Date: ${create_date}
+
+"""
+from alembic import op
+import sqlalchemy as sa
+${imports if imports else ""}
+
+# revision identifiers, used by Alembic.
+revision = ${repr(up_revision)}
+down_revision = ${repr(down_revision)}
+branch_labels = ${repr(branch_labels)}
+depends_on = ${repr(depends_on)}
+
+
+def upgrade() -> None:
+    """Apply migration changes to upgrade the database schema."""
+    ${upgrades if upgrades else "pass"}
+
+
+def downgrade() -> None:
+    """Revert migration changes to downgrade the database schema."""
+    ${downgrades if downgrades else "pass"}

app-hooks/post-installation/00-setup-trusted-domains.sh

@@ -3,3 +3,9 @@
 set -euox pipefail
 
 php /var/www/html/occ config:system:set trusted_domains 2 --value=host.docker.internal
+
+# Set overwrite settings for URL generation (needed for OIDC discovery to return correct URLs)
+# These ensure that URLs generated by Nextcloud include the correct host:port
+php /var/www/html/occ config:system:set overwritehost --value="localhost:8080"
+php /var/www/html/occ config:system:set overwriteprotocol --value="http"
+php /var/www/html/occ config:system:set overwrite.cli.url --value="http://localhost:8080"

app-hooks/post-installation/10-install-news-app.sh

@@ -0,0 +1,5 @@
+#!/bin/bash
+
+set -euox pipefail
+
+php /var/www/html/occ app:enable news

app-hooks/post-installation/20-install-astrolabe-app.sh

@@ -0,0 +1,36 @@
+#!/bin/bash
+
+set -euox pipefail
+
+echo "Installing Astrolabe app for testing..."
+
+# Check if development astrolabe app is mounted at /opt/apps/astrolabe
+if [ -d /opt/apps/astrolabe ]; then
+    echo "Development astrolabe app found at /opt/apps/astrolabe"
+
+    # Remove any existing astrolabe app in custom_apps (from app store or old symlink)
+    if [ -e /var/www/html/custom_apps/astrolabe ]; then
+        echo "Removing existing astrolabe in custom_apps..."
+        rm -rf /var/www/html/custom_apps/astrolabe
+    fi
+
+    # Create symlink from custom_apps to the mounted development version
+    # Per Nextcloud docs: apps outside server root need symlinks in server root
+    echo "Creating symlink: custom_apps/astrolabe -> /opt/apps/astrolabe"
+    ln -sf /opt/apps/astrolabe /var/www/html/custom_apps/astrolabe
+
+    echo "Enabling astrolabe app from /opt/apps (development mode via symlink)"
+    php /var/www/html/occ app:enable astrolabe
+elif [ -d /var/www/html/custom_apps/astrolabe ]; then
+    echo "astrolabe app directory found in custom_apps (already installed)"
+    php /var/www/html/occ app:enable astrolabe
+else
+    echo "astrolabe app not found, installing from app store..."
+    php /var/www/html/occ app:install astrolabe
+    php /var/www/html/occ app:enable astrolabe
+fi
+
+echo "✓ Astrolabe app installed successfully"
+echo ""
+echo "Note: MCP server configuration is managed dynamically during tests"
+echo "      to support testing multiple MCP server deployments."

charts/nextcloud-mcp-server/.cz.toml

@@ -0,0 +1,25 @@
+[tool.commitizen]
+name = "cz_conventional_commits"
+version = "0.54.0"
+tag_format = "nextcloud-mcp-server-$version"
+version_scheme = "semver"
+update_changelog_on_bump = true
+major_version_zero = true
+
+# Update chart version only (NOT appVersion)
+version_files = [
+    "Chart.yaml:^version:"
+]
+
+# Ignore tags from other components
+ignored_tag_formats = [
+    "v*",              # MCP server tags
+    "astrolabe-v*",    # Astrolabe tags
+]
+
+# Filter commits by scope
+# Includes helm-scoped commits AND MCP server version bumps (which update appVersion)
+[tool.commitizen.customize]
+changelog_pattern = "^((feat|fix|docs|refactor|perf|test|build|ci|chore)\\(helm\\)(!)?:|bump: version.*→.*)"
+schema_pattern = "^(feat|fix|docs|refactor|perf|test|build|ci|chore)\\(helm\\)(!)?:\\s.+"
+message_template = "{{change_type}}(helm): {{message}}"

charts/nextcloud-mcp-server/CHANGELOG.md

@@ -0,0 +1,746 @@
+# Changelog - Helm Chart
+
+All notable changes to the Helm chart will be documented in this file.
+
+The format is based on [Keep a Changelog](https://keepachangelog.com/en/1.0.0/),
+and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0.html).
+
+
+### Added
+- Initial independent versioning release
+- Support for Nextcloud MCP server deployment
+- Qdrant subchart integration
+- Ollama subchart integration
+- Configurable resource limits
+- Grafana dashboard annotations
+
+## nextcloud-mcp-server-0.54.0 (2025-12-19)
+
+### Feat
+
+- **ci**: implement monorepo-aware version bumping workflow
+- **astrolabe**: add Nextcloud App Store deployment automation
+- configure commitizen monorepo with independent versioning
+
+### Fix
+
+- **ci**: improve versioning and error handling
+- **ci**: address critical workflow and validation issues
+- **astrolabe**: address code review feedback
+
+## nextcloud-mcp-server-0.53.0 (2025-12-19)
+
+### Feat
+
+- add Alembic database migration system
+- make chunk modal title clickable link to documents
+- add native Plotly hover styling for clickable points
+- add click interactivity to Plotly 3D scatter chart
+- improve chunk viewer with fixed navigation and markdown rendering
+- **astrolabe**: enable multi-select for document types and refactor PDF viewer
+- **auth**: implement refresh token rotation for Nextcloud OIDC
+- **astrolabe**: enhance unified search and add webhook management
+- **astrolabe**: add webhook management UI to admin settings
+- **astrolabe**: add OAuth token refresh and webhook presets
+- **search**: add file_path metadata and chunk offsets to search results
+- **astrolabe**: use proper icons and thumbnails in unified search
+- **astrolabe**: add admin search settings and enhanced UI
+- **astrolabe**: add unified search provider with clickable file links
+- **astrolabe**: add 3D PCA visualization for semantic search
+- **astrolabe**: add Nextcloud PHP app for MCP server management
+- **vector-sync**: enable background sync in OAuth mode
+
+### Fix
+
+- **security**: address critical security issues from PR #401 code review
+- **oauth**: enable PKCE for all clients and add token_broker to oauth_context
+- **astrolabe**: revert invalid files_pdfviewer URL for file links
+- resolve type checking warnings for CI
+- move Alembic to package submodule for Docker compatibility
+- update unified search results to match chunk viz display
+- **astrolabe**: handle OAuth refresh token rotation
+- address critical code review issues (4 fixes)
+- resolve CI linting issues for Astroglobe
+
+### Refactor
+
+- **astrolabe**: extract PDF viewer to dedicated component
+- **astrolabe**: reframe UI as semantic search service
+
+## nextcloud-mcp-server-0.52.1 (2025-12-13)
+
+## nextcloud-mcp-server-0.52.0 (2025-12-13)
+
+## nextcloud-mcp-server-0.51.0 (2025-12-13)
+
+### Feat
+
+- **vector**: add Deck card vector search with visualization support
+- **vector-viz**: add news_item support for links and chunk expansion
+
+### Perf
+
+- **deck**: optimize card lookup by storing board_id/stack_id in metadata
+
+## nextcloud-mcp-server-0.50.2 (2025-12-13)
+
+### Fix
+
+- **news**: revert get_item() to use get_items() + filter
+
+## nextcloud-mcp-server-0.50.1 (2025-12-12)
+
+### Fix
+
+- Disable DNS rebinding protection for containerized deployments
+- **deps**: update dependency mcp to >=1.23,<1.24
+
+## nextcloud-mcp-server-0.50.0 (2025-12-11)
+
+### Feat
+
+- add MCP tool annotations for enhanced UX
+
+### Fix
+
+- address PR review feedback
+
+## nextcloud-mcp-server-0.49.2 (2025-12-09)
+
+### Fix
+
+- Update lockfile
+
+## nextcloud-mcp-server-0.49.1 (2025-12-09)
+
+### Fix
+
+- Revert mcp version <1.23
+
+## nextcloud-mcp-server-0.49.0 (2025-12-08)
+
+### Fix
+
+- resolve all type checking errors (8 errors fixed)
+- **deps**: update dependency mcp to >=1.23,<1.24
+
+### Perf
+
+- **news**: use direct API endpoint for get_item()
+
+## nextcloud-mcp-server-0.48.5 (2025-11-28)
+
+### Feat
+
+- **news**: add Nextcloud News app integration
+
+### Fix
+
+- **deps**: update dependency pillow to v12
+
+### Refactor
+
+- **news**: simplify vector sync to fetch all items
+
+## nextcloud-mcp-server-0.48.4 (2025-11-23)
+
+### Fix
+
+- Add rate limit retry logic to OpenAI provider
+
+## nextcloud-mcp-server-0.48.3 (2025-11-23)
+
+### Fix
+
+- Increase MCP sampling timeout to 5 minutes for slower LLMs
+
+## nextcloud-mcp-server-0.48.2 (2025-11-23)
+
+### Fix
+
+- Share vector sync state with FastMCP session lifespan via module singleton
+
+## nextcloud-mcp-server-0.48.1 (2025-11-23)
+
+## nextcloud-mcp-server-0.48.0 (2025-11-23)
+
+## nextcloud-mcp-server-0.47.0 (2025-11-23)
+
+### Feat
+
+- Add tag management methods to WebDAV client
+- Add OpenAI provider support for embeddings and generation
+
+### Fix
+
+- Share vector sync state with FastMCP session lifespan via module singleton
+- Use WebDAV for tag creation and add LLM-as-a-judge for RAG tests
+
+### Refactor
+
+- Move background tasks to server lifespan and deprecate SSE transport
+
+## nextcloud-mcp-server-0.46.2 (2025-11-22)
+
+### Fix
+
+- **smithery**: Enable JSON response format for scanner compatibility
+
+## nextcloud-mcp-server-0.46.1 (2025-11-22)
+
+### Perf
+
+- Optimize vector viz search performance
+
+## nextcloud-mcp-server-0.46.0 (2025-11-22)
+
+### Feat
+
+- Add Smithery CLI deployment support
+- Implement ADR-016 Smithery stateless deployment mode
+
+### Fix
+
+- **smithery**: Add JSON Schema metadata to mcp-config endpoint
+- **smithery**: Use container runtime pattern for config discovery
+- Add Smithery lifespan and auth mode detection
+
+## nextcloud-mcp-server-0.45.0 (2025-11-22)
+
+### Feat
+
+- Add context expansion to semantic search with chunk overlap removal
+- Use Ollama native batch API in embed_batch()
+- Implement Qdrant placeholder state management
+- Switch files to use numeric IDs with file_path resolution
+- Implement per-chunk vector visualization with context expansion
+
+### Fix
+
+- Use alpha_composite for proper RGBA highlight blending
+- Remove pymupdf.layout.activate() to fix page_chunks behavior
+- Centralize PDF processing and generate separate images per chunk
+- Set is_placeholder=False in processor to fix search filtering
+- Increase placeholder staleness threshold to 5x scan interval
+- Add placeholder staleness check to prevent duplicate processing
+- Use empty SparseVector instead of None for placeholders
+- Return empty array instead of null for query_coords when no results
+- Align PDF text extraction between indexing and context expansion
+- Update models and viz to use int-only doc_id
+- Reconstruct full content for notes to match indexed offsets
+- Add async/await, PDF metadata, and type safety fixes
+
+### Refactor
+
+- Simplify PDF text extraction with single to_markdown call
+
+### Perf
+
+- Optimize PDF processing with parallel extraction and single-render highlights
+
+## nextcloud-mcp-server-0.44.1 (2025-11-21)
+
+### Fix
+
+- **deps**: update dependency mcp to >=1.22,<1.23
+
+## nextcloud-mcp-server-0.44.0 (2025-11-19)
+
+### Feat
+
+- Improve vector visualization with static assets and fixes
+- Redesign UI to match Nextcloud ecosystem aesthetic
+
+### Fix
+
+- Improve 3D plot rendering with explicit dimensions and window resize support
+- Preserve 3D plot camera and improve documentation
+- Preserve 3D plot camera position and fix CSS loading
+
+## nextcloud-mcp-server-0.43.0 (2025-11-18)
+
+### Feat
+
+- Replace custom document chunker with LangChain MarkdownTextSplitter
+
+## nextcloud-mcp-server-0.42.0 (2025-11-17)
+
+### Feat
+
+- **viz**: Add dual-score display and improve UI controls
+
+## nextcloud-mcp-server-0.41.0 (2025-11-17)
+
+### Feat
+
+- add configurable fusion algorithms for BM25 hybrid search
+- add chunk position tracking to vector indexing and search
+- add vector viz template and chunk context endpoint
+
+### Fix
+
+- prevent infinite loop in DocumentChunker with position tracking
+- Relax SearchResult validation to support DBSF fusion scores > 1.0
+
+## nextcloud-mcp-server-0.40.0 (2025-11-16)
+
+### Feat
+
+- add unified provider architecture with Amazon Bedrock support
+
+### Fix
+
+- suppress Starlette middleware type warnings in ty checker
+
+## nextcloud-mcp-server-0.39.0 (2025-11-16)
+
+## nextcloud-mcp-server-0.38.0 (2025-11-16)
+
+### Feat
+
+- add concurrent uploads and --force flag to upload command
+- implement RAG evaluation framework with CLI tooling
+- Add OpenTelemetry tracing to @instrument_tool decorator
+- Implement BM25 hybrid search with native Qdrant RRF fusion
+
+### Fix
+
+- download qrels from BEIR ZIP instead of HuggingFace
+- Handle named vectors in visualization and semantic search
+- Update vizApp to use bm25_hybrid algorithm and remove deprecated weights
+- Update viz routes to use BM25 hybrid search after refactor
+
+### Refactor
+
+- migrate asyncio to anyio for consistent structured concurrency
+- replace httpx client with NextcloudClient in upload command
+
+### Perf
+
+- Eliminate double-fetching in semantic search sampling
+- fix vector viz search performance and visual encoding
+- make note deletion concurrent in upload --force
+
+## nextcloud-mcp-server-0.36.0 (2025-11-15)
+
+### BREAKING CHANGE
+
+- Search algorithms now require Qdrant to be populated.
+Vector sync must be enabled and documents indexed for search to work.
+
+### Feat
+
+- Normalize hybrid search RRF scores to 0-1 range
+- Enhance vector visualization UI and parallelize search verification
+- Add Vector Viz tab to app home page
+- Add vector visualization pane with multi-select document types
+- Implement custom PCA to remove sklearn dependency
+- Add multi-document Protocol with cross-app search support
+- Update nc_semantic_search tool with algorithm selection
+- Implement unified search algorithm module
+
+### Fix
+
+- Reorder tabs and fix viz pane session access
+
+### Refactor
+
+- Optimize Nextcloud access verification with centralized filtering
+- Make all search algorithms query Qdrant payload, not Nextcloud
+
+### Perf
+
+- Exclude vector-sync status polling from distributed tracing
+
+## nextcloud-mcp-server-0.35.0 (2025-11-15)
+
+### Feat
+
+- Enable SSE transport for mcp service and update test fixtures
+
+## nextcloud-mcp-server-0.34.2 (2025-11-13)
+
+### Fix
+
+- Use NEXTCLOUD_OIDC_CLIENT_ID/SECRET env vars consistently
+- return all notes when search query is empty
+
+## nextcloud-mcp-server-0.34.0 (2025-11-13)
+
+### Feat
+
+- Complete Phase 5 - Instrument all 93 MCP tools
+- Add instrumentation decorator and apply to notes tools (Phase 5)
+- Add OAuth token and database metrics (Phases 3-4)
+- Add metrics instrumentation for queue, health, and database operations
+
+## nextcloud-mcp-server-0.33.1 (2025-11-13)
+
+### Fix
+
+- Move grafana_folder from labels to annotations
+
+## nextcloud-mcp-server-0.33.0 (2025-11-13)
+
+### Feat
+
+- Add Grafana dashboard and vector sync metric instrumentation
+
+## nextcloud-mcp-server-0.32.1 (2025-11-12)
+
+### Fix
+
+- add dynamic dimension detection for Ollama embedding models
+
+## nextcloud-mcp-server-0.32.0 (2025-11-11)
+
+### Feat
+
+- **ollama**: Pull model on startup if not available in ollama
+- add dynamic vector sync status updates with htmx polling
+- add webhook management UI and BeforeNodeDeletedEvent support
+- validate Nextcloud webhook schemas and document findings
+
+### Fix
+
+- improve webapp tab UI with CSS Grid and viewport-filling container
+
+### Refactor
+
+- move webapp from /user/page to /app
+- consolidate database storage for webhooks and OAuth tokens
+
+## nextcloud-mcp-server-0.31.1 (2025-11-10)
+
+### Refactor
+
+- simplify OpenTelemetry tracing configuration
+
+## nextcloud-mcp-server-0.31.0 (2025-11-10)
+
+### Feat
+
+- skip tracing for health and metrics endpoints
+
+### Fix
+
+- add retry logic for ETag conflicts in category change test
+- optimize Notes API pagination with pruneBefore parameter
+
+## nextcloud-mcp-server-0.30.0 (2025-11-10)
+
+### Feat
+
+- **helm**: Add document chunking configuration
+- **vector**: Add configurable chunk size and overlap for document embedding
+- **vector**: Support multiple embedding models with auto-generated collection names
+
+### Fix
+
+- Support in-memory Qdrant for CI testing
+
+## nextcloud-mcp-server-0.29.2 (2025-11-09)
+
+### Fix
+
+- **helm**: Set default strategy to Recreate
+
+## nextcloud-mcp-server-0.29.1 (2025-11-09)
+
+### Fix
+
+- **observability**: isolate metrics endpoint to dedicated port
+
+## nextcloud-mcp-server-0.29.0 (2025-11-09)
+
+### Feat
+
+- **helm**: Add observability support with ServiceMonitor and Grafana dashboard
+
+### Fix
+
+- **readiness**: Only check external Qdrant in network mode
+
+## nextcloud-mcp-server-0.28.0 (2025-11-09)
+
+### Feat
+
+- **observability**: Add comprehensive monitoring with Prometheus and OpenTelemetry
+
+### Fix
+
+- **vector**: Handle missing 'modified' field in notes gracefully
+
+## nextcloud-mcp-server-0.27.3 (2025-11-09)
+
+### Fix
+
+- **ci**: Use helm dependency build instead of update to use Chart.lock
+
+## nextcloud-mcp-server-0.27.2 (2025-11-09)
+
+### Fix
+
+- **helm**: update Qdrant dependency condition to match new mode structure
+
+## nextcloud-mcp-server-0.27.1 (2025-11-09)
+
+### Feat
+
+- **helm**: add Qdrant local mode support with three deployment options [skip ci]
+- add Qdrant local mode support with in-memory and persistent storage
+- implement ADR-009 - refactor semantic search to use generic semantic:read scope
+- implement MCP sampling for semantic search RAG (ADR-008)
+- add optional vector database and semantic search to helm chart
+- add vector sync processing status to /user/page endpoint
+- implement semantic search tool and fix vector sync issues (ADR-007 Phase 3)
+- implement vector sync scanner and processor (ADR-007 Phase 2)
+
+### Fix
+
+- **ci**: add Helm repository setup to chart release workflow
+- implement deletion grace period and vector sync status tool
+- remove unnecessary urllib3<2.0 constraint
+- integrate vector sync tasks with Starlette lifespan for streamable-http
+
+### Refactor
+
+- migrate vector sync from asyncio.Queue to anyio memory object streams
+- update to Qdrant query_points API and fix Playwright Keycloak login
+
+## nextcloud-mcp-server-0.26.1 (2025-11-08)
+
+### Fix
+
+- **deps**: update dependency mcp to >=1.21,<1.22
+
+## nextcloud-mcp-server-0.26.0 (2025-11-08)
+
+### Feat
+
+- add real elicitation integration test with python-sdk MCP client
+- unify session architecture and enhance login status visibility
+
+### Fix
+
+- Consolidate OAuth callbacks and implement PKCE for all flows
+
+## nextcloud-mcp-server-0.25.0 (2025-11-05)
+
+### BREAKING CHANGE
+
+- All OAuth deployments must be reconfigured to specify
+resource URIs (NEXTCLOUD_MCP_SERVER_URL and NEXTCLOUD_RESOURCE_URI) and
+choose between multi-audience or token exchange mode.
+
+### Feat
+
+- Implement ADR-005 unified token verifier to eliminate token passthrough vulnerability
+
+### Fix
+
+- Implement proper OAuth resource parameters and PRM-based discovery
+- Simplify token verifier to be RFC 7519 compliant
+- Use Keycloak client ID for NEXTCLOUD_RESOURCE_URI in token exchange
+- Correct OAuth token audience validation for multi-audience mode
+
+### Refactor
+
+- Eliminate duplicate validation logic in UnifiedTokenVerifier
+
+## nextcloud-mcp-server-0.24.1 (2025-11-04)
+
+### Fix
+
+- **deps**: update dependency mcp to >=1.20,<1.21
+
+## nextcloud-mcp-server-0.24.0 (2025-11-04)
+
+### Feat
+
+- add scope protection to OAuth provisioning tools
+- enable authorization services for token exchange in Keycloak
+- implement scope-based audience mapping and RFC 9728 support
+- integrate token exchange into MCP server application
+- implement RFC 8693 Standard Token Exchange for Keycloak
+- Add userinfo route/page
+- add browser-based user info page with separate OAuth flow
+- Implement ADR-004 Progressive Consent foundation (partial)
+- Complete ADR-004 Progressive Consent OAuth flows implementation
+- Implement ADR-004 Progressive Consent foundation components
+- Implement ADR-004 Hybrid Flow with comprehensive integration tests
+
+### Fix
+
+- add missing await for get_nextcloud_client in capabilities resource
+- use valid Fernet encryption keys in token exchange tests
+- accept resource URL in token audience for Nextcloud JWT tokens
+- remove token-exchange-nextcloud scope and accept tokens without audience
+- move audience mapper from scope to nextcloud-mcp-server client
+- move token-exchange-nextcloud from default to optional scopes
+- restructure routes to prevent SessionAuthBackend from interfering with FastMCP OAuth
+- allow OAuth Bearer tokens on /mcp endpoint by excluding from session auth
+- correct OAuth token audience validation using RFC 8707 resource parameter
+- remove remaining references to deleted oauth_callback and oauth_token
+- remove Hybrid Flow, make Progressive Consent default (ADR-004)
+- browser OAuth userinfo endpoint and refresh token rotation
+- make ENABLE_PROGRESSIVE_CONSENT consistently opt-in (default false)
+- make provisioning checks opt-in (default false)
+- Disable Progressive Consent for mcp-oauth to enable Hybrid Flow tests
+
+### Refactor
+
+- integrate token exchange into unified get_client() pattern
+
+## nextcloud-mcp-server-0.23.0 (2025-11-03)
+
+### Feat
+
+- Auto-configure impersonation role in Keycloak realm import
+- Implement dual-tier token exchange (Standard V2 + Legacy V1 impersonation)
+- Add Keycloak external IdP integration with custom scopes
+- Implement RFC 8693 token exchange for Keycloak (ADR-002 Tier 2)
+- Add Keycloak OAuth provider support with refresh token storage
+
+### Fix
+
+- Complete Keycloak external IdP integration with all tests passing
+- Complete Keycloak external IdP integration with all tests passing
+- Update DCR token_type tests for OIDC app changes
+
+### Refactor
+
+- Remove NEXTCLOUD_OIDC_CLIENT_STORAGE environment variable
+- Remove unnecessary user_oidc patch - CORSMiddleware patch is sufficient
+- Unify OAuth configuration to be provider-agnostic
+
+## nextcloud-mcp-server-0.22.7 (2025-10-29)
+
+### Fix
+
+- **helm**: Remove image tag overide
+
+## nextcloud-mcp-server-0.22.6 (2025-10-29)
+
+### Fix
+
+- **helm**: Update helm chart with extraArgs
+
+## nextcloud-mcp-server-0.22.5 (2025-10-29)
+
+### Fix
+
+- Update helm chart variables
+
+## nextcloud-mcp-server-0.22.4 (2025-10-29)
+
+### Fix
+
+- **helm**: Update helm version with release
+- **helm**: Update helm version with release
+- **helm**: Update helm version with release
+
+## nextcloud-mcp-server-0.1.1 (2025-10-29)
+
+### Fix
+
+- **helm**: Update helm version with release
+- Trigger release
+
+## nextcloud-mcp-server-0.1.0 (2025-10-29)
+
+### BREAKING CHANGE
+
+- FASTMCP_-prefixed env vars have been replaced by CLI
+arguments. Refer to the README for updated usage.
+
+### Feat
+
+- **server**: Add /live & /health endpoints
+- Initialize helm chart
+- Add text processing background worker for telling client about progress
+- **auth**: Add support for client registration deletion
+- Split read/write scopes into app:read/write scopes
+- Enable token introspection for opaque tokens
+- **server**: Add support for custom OIDC scopes and permissions via JWTs
+- Initialize JWT-scoped tools
+- **caldav**: Add support for tasks
+- **webdav**: Add search and list favorite response tools
+- **cookbook**: Add full Cookbook app support with 13 tools and 2 resources
+- Add Groups API client
+- add sharing API client and server tools
+- **server**: Experimental support for OAuth2/OIDC authentication
+- **users**: Initialize user API client
+- **server**: Add support for `streamable-http` transport type
+- Add WebDAV resource copy functionality
+- Add WebDAV resource move/rename functionality
+- **deck**: Add support for stack, cards, labels
+- **deck**: Initialize Deck app client/server
+- **cli**: Replace `mcp run` with click CLI and runtime options
+- **client**: Preserve fields when modifying contacts/calendar resources
+- **server**: Add structured output to all tool/resource output
+- **contacts**: Initialize Contacts App
+- **calendar**: add comprehensive Calendar app support via CalDAV protocol
+- Update webdav client create_directory method to handle recursive directories
+- **webdav**: add complete file system support
+- Add TablesClient and associated tools
+- Switch to using async client
+- **notes**: Add append to note functionality
+
+### Fix
+
+- Add support for RFC 7592 client registration and deletion
+- Update webdav models for proper serialization
+- **deps**: update dependency mcp to >=1.19,<1.20
+- Add CORS middleware to allow browser-based clients like MCP Inspector
+- Use occ-created OAuth clients with allowed_scopes for all tests
+- Separate OAuth fixtures for opaque vs JWT tokens
+- **caldav**: Fix caldav search() due to missing todos
+- **caldav**: Check that calendar exists after creation to avoid race condition
+- **caldav**: Properly parse datetimes as vDDDTypes
+- Increase HTTP client timeout to 30s
+- Handle RequestError in mcp tools
+- **deps**: update dependency mcp to >=1.18,<1.19
+- **deps**: update dependency pillow to v12
+- **oauth**: Remove the option to force_register new clients
+- Update user/groups API to OCS v2
+- **deps**: update dependency mcp to >=1.17,<1.18
+- **deps**: update dependency mcp to >=1.16,<1.17
+- **deps**: update dependency mcp to >=1.15,<1.16
+- **docker**: Provide --host 0.0.0.0 in default docker image
+- **deps**: update dependency mcp to >=1.13,<1.14
+- **server**: Replace ErrorResponses with standard McpErrors
+- **notes**: Include ETags in responses to avoid accidently updates
+- **notes**: Remove note contents from responses to reduce token usage
+- **model**: Serialize timestamps in RFC3339 format
+- **client**: Use paging to fetch all notes
+- **client**: Strip cookies from responses to avoid falsely raising CSRF errors
+- **calendar**: Fix iCalendar date vs datetime format
+- **calendar**: Remove try/except in calendar API
+- apply ruff formatting to pass CI checks
+- **calendar**: address PR feedback from maintainer
+- apply ruff formatting to test_webdav_operations.py
+- **deps**: update dependency mcp to >=1.10,<1.11
+- update tests
+- Commitizen release process
+- Do not update dependencies when running in Dockerfile
+- Configure logging
+- Limit search results to notes with score > 0.5
+- Install deps before checking service
+- **deps**: update dependency mcp to >=1.9,<1.10
+
+### Refactor
+
+- Transform document parsing into pluggable processor architecture
+- Update JWT client to use DCR, re-enable tool filtering
+- Migrate from internal CalendarClient to caldav library
+- Unify logging & remove factory deployment
+- Add tools for all resources to enable tool-only workflows
+- Add `http` to --transport option
+- Use _make_request where available
+- **calendar**: optimize logging for production readiness
+- Modularize NC and Notes app client
+
+### Perf
+
+- **notes**: Improve notes search performance using async iterators

charts/nextcloud-mcp-server/Chart.lock

@@ -1,9 +1,9 @@
 dependencies:
 - name: qdrant
   repository: https://qdrant.github.io/qdrant-helm
-  version: 1.16.0
+  version: 1.16.3
 - name: ollama
   repository: https://otwld.github.io/ollama-helm
-  version: 1.35.0
+  version: 1.36.0
-digest: sha256:da8db198b12ce0252df220fabb297cfe69186edb8e67952c52e05de778189b92
+digest: sha256:7f0979ec4110ff41ebeb55bf586b41366a350cc39fe65a2da7d2da03f723fe9b
-generated: "2025-11-21T11:09:07.997781541Z"
+generated: "2025-12-22T11:09:39.166328543Z"

charts/nextcloud-mcp-server/Chart.yaml

@@ -2,8 +2,8 @@ apiVersion: v2
 name: nextcloud-mcp-server
 description: A Helm chart for Nextcloud MCP Server - enables AI assistants to interact with Nextcloud
 type: application
-version: 0.48.2
+version: 0.54.0
-appVersion: "0.48.2"
+appVersion: "0.57.0"
 keywords:
   - nextcloud
   - mcp
@@ -27,10 +27,10 @@ annotations:
   grafana_dashboard_folder: "Nextcloud MCP"
 dependencies:
   - name: qdrant
-    version: "1.16.0"
+    version: "1.16.3"
     repository: https://qdrant.github.io/qdrant-helm
     condition: qdrant.networkMode.deploySubchart
   - name: ollama
-    version: "1.35.0"
+    version: "1.36.0"
     repository: https://otwld.github.io/ollama-helm
     condition: ollama.enabled

charts/nextcloud-mcp-server/templates/_helpers.tpl

@@ -72,6 +72,28 @@ Create the name of the secret to use for basic auth
 {{- end }}
 {{- end }}
 
+{{/*
+Create the name of the secret to use for multi-user basic auth
+*/}}
+{{- define "nextcloud-mcp-server.multiUserBasicSecretName" -}}
+{{- if .Values.auth.multiUserBasic.existingSecret }}
+{{- .Values.auth.multiUserBasic.existingSecret }}
+{{- else }}
+{{- include "nextcloud-mcp-server.fullname" . }}-multi-user-basic
+{{- end }}
+{{- end }}
+
+{{/*
+Create the name of the PVC to use for multi-user basic token storage
+*/}}
+{{- define "nextcloud-mcp-server.multiUserBasicPvcName" -}}
+{{- if .Values.auth.multiUserBasic.persistence.existingClaim }}
+{{- .Values.auth.multiUserBasic.persistence.existingClaim }}
+{{- else }}
+{{- include "nextcloud-mcp-server.fullname" . }}-token-storage
+{{- end }}
+{{- end }}
+
 {{/*
 Create the name of the secret to use for OAuth
 */}}

charts/nextcloud-mcp-server/templates/deployment.yaml

@@ -68,7 +68,7 @@ spec:
             - name: NEXTCLOUD_HOST
               value: {{ .Values.nextcloud.host | quote }}
             {{- if eq .Values.auth.mode "basic" }}
-            # Basic auth mode
+            # Basic auth mode (single-user)
             - name: NEXTCLOUD_USERNAME
               valueFrom:
                 secretKeyRef:
@@ -79,6 +79,41 @@ spec:
                 secretKeyRef:
                   name: {{ include "nextcloud-mcp-server.basicAuthSecretName" . }}
                   key: {{ .Values.auth.basic.passwordKey }}
+            {{- else if eq .Values.auth.mode "multi-user-basic" }}
+            # Multi-user BasicAuth mode (pass-through)
+            - name: ENABLE_MULTI_USER_BASIC_AUTH
+              value: "true"
+            - name: NEXTCLOUD_MCP_SERVER_URL
+              value: {{ include "nextcloud-mcp-server.mcpServerUrl" . | quote }}
+            - name: NEXTCLOUD_PUBLIC_ISSUER_URL
+              value: {{ include "nextcloud-mcp-server.publicIssuerUrl" . | quote }}
+            {{- if .Values.auth.multiUserBasic.enableOfflineAccess }}
+            # Background operations with app passwords
+            - name: ENABLE_OFFLINE_ACCESS
+              value: "true"
+            - name: TOKEN_STORAGE_DB
+              value: {{ .Values.auth.multiUserBasic.tokenStorageDb | quote }}
+            - name: TOKEN_ENCRYPTION_KEY
+              valueFrom:
+                secretKeyRef:
+                  name: {{ include "nextcloud-mcp-server.multiUserBasicSecretName" . }}
+                  key: {{ .Values.auth.multiUserBasic.tokenEncryptionKeyKey }}
+            - name: NEXTCLOUD_OIDC_SCOPES
+              value: {{ .Values.auth.multiUserBasic.scopes | quote }}
+            {{- if .Values.auth.multiUserBasic.clientId }}
+            # Static OAuth credentials (optional - uses DCR if not provided)
+            - name: NEXTCLOUD_OIDC_CLIENT_ID
+              valueFrom:
+                secretKeyRef:
+                  name: {{ include "nextcloud-mcp-server.multiUserBasicSecretName" . }}
+                  key: {{ .Values.auth.multiUserBasic.clientIdKey }}
+            - name: NEXTCLOUD_OIDC_CLIENT_SECRET
+              valueFrom:
+                secretKeyRef:
+                  name: {{ include "nextcloud-mcp-server.multiUserBasicSecretName" . }}
+                  key: {{ .Values.auth.multiUserBasic.clientSecretKey }}
+            {{- end }}
+            {{- end }}
             {{- else if eq .Values.auth.mode "oauth" }}
             # OAuth mode
             - name: NEXTCLOUD_MCP_SERVER_URL
@@ -251,6 +286,10 @@ spec:
             - name: oauth-storage
               mountPath: /app/.oauth
             {{- end }}
+            {{- if and (eq .Values.auth.mode "multi-user-basic") .Values.auth.multiUserBasic.enableOfflineAccess .Values.auth.multiUserBasic.persistence.enabled }}
+            - name: token-storage
+              mountPath: /app/data
+            {{- end }}
             {{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled }}
             - name: qdrant-data
               mountPath: /app/data
@@ -266,6 +305,11 @@ spec:
           persistentVolumeClaim:
             claimName: {{ include "nextcloud-mcp-server.oauthPvcName" . }}
         {{- end }}
+        {{- if and (eq .Values.auth.mode "multi-user-basic") .Values.auth.multiUserBasic.enableOfflineAccess .Values.auth.multiUserBasic.persistence.enabled }}
+        - name: token-storage
+          persistentVolumeClaim:
+            claimName: {{ include "nextcloud-mcp-server.multiUserBasicPvcName" . }}
+        {{- end }}
         {{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled }}
         - name: qdrant-data
           persistentVolumeClaim:

charts/nextcloud-mcp-server/templates/pvc.yaml

@@ -16,6 +16,24 @@ spec:
       storage: {{ .Values.auth.oauth.persistence.size }}
 {{- end }}
 ---
+{{- if and (eq .Values.auth.mode "multi-user-basic") .Values.auth.multiUserBasic.enableOfflineAccess .Values.auth.multiUserBasic.persistence.enabled (not .Values.auth.multiUserBasic.persistence.existingClaim) }}
+apiVersion: v1
+kind: PersistentVolumeClaim
+metadata:
+  name: {{ include "nextcloud-mcp-server.fullname" . }}-token-storage
+  labels:
+    {{- include "nextcloud-mcp-server.labels" . | nindent 4 }}
+spec:
+  accessModes:
+    - {{ .Values.auth.multiUserBasic.persistence.accessMode }}
+  {{- if .Values.auth.multiUserBasic.persistence.storageClass }}
+  storageClassName: {{ .Values.auth.multiUserBasic.persistence.storageClass }}
+  {{- end }}
+  resources:
+    requests:
+      storage: {{ .Values.auth.multiUserBasic.persistence.size }}
+{{- end }}
+---
 {{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled (not .Values.qdrant.localPersistence.existingClaim) }}
 apiVersion: v1
 kind: PersistentVolumeClaim

charts/nextcloud-mcp-server/templates/secret.yaml

@@ -13,6 +13,24 @@ data:
 {{- end }}
 {{- end }}
 ---
+{{- if eq .Values.auth.mode "multi-user-basic" }}
+{{- if and .Values.auth.multiUserBasic.enableOfflineAccess (not .Values.auth.multiUserBasic.existingSecret) }}
+apiVersion: v1
+kind: Secret
+metadata:
+  name: {{ include "nextcloud-mcp-server.fullname" . }}-multi-user-basic
+  labels:
+    {{- include "nextcloud-mcp-server.labels" . | nindent 4 }}
+type: Opaque
+data:
+  {{ .Values.auth.multiUserBasic.tokenEncryptionKeyKey }}: {{ .Values.auth.multiUserBasic.tokenEncryptionKey | b64enc | quote }}
+  {{- if .Values.auth.multiUserBasic.clientId }}
+  {{ .Values.auth.multiUserBasic.clientIdKey }}: {{ .Values.auth.multiUserBasic.clientId | b64enc | quote }}
+  {{ .Values.auth.multiUserBasic.clientSecretKey }}: {{ .Values.auth.multiUserBasic.clientSecret | b64enc | quote }}
+  {{- end }}
+{{- end }}
+{{- end }}
+---
 {{- if eq .Values.auth.mode "oauth" }}
 {{- if and .Values.auth.oauth.clientId (not .Values.auth.oauth.existingSecret) }}
 apiVersion: v1

charts/nextcloud-mcp-server/values.yaml

@@ -33,14 +33,15 @@ nextcloud:
   publicIssuerUrl: ""
 
 # Authentication configuration
-# Choose either basic auth OR oauth (not both)
+# Choose one mode: "basic", "multi-user-basic", or "oauth"
 auth:
-  # Authentication mode: "basic" or "oauth"
+  # Authentication mode: "basic", "multi-user-basic", or "oauth"
-  # basic: Uses username/password (recommended for most users)
+  # basic: Single-user with username/password (recommended for personal use)
+  # multi-user-basic: Multi-user with BasicAuth pass-through (credentials in request headers)
   # oauth: Uses OAuth2/OIDC (experimental, requires patches)
   mode: basic
 
-  # Basic authentication settings
+  # Basic authentication settings (single-user mode)
   basic:
     # Nextcloud username (ignored if existingSecret is set)
     username: ""
@@ -58,6 +59,47 @@ auth:
     usernameKey: "username"
     passwordKey: "password"
 
+  # Multi-user BasicAuth settings (pass-through mode)
+  # Users provide credentials in request headers (Authorization: Basic ...)
+  # Server optionally stores app passwords for background operations
+  multiUserBasic:
+    # Enable offline access (background operations using app passwords via Astrolabe)
+    # When enabled, requires token encryption key. OAuth client credentials are optional (uses DCR if not provided)
+    enableOfflineAccess: false
+    # Token encryption key (required if enableOfflineAccess: true, ignored if existingSecret is set)
+    # Generate with: python -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"
+    tokenEncryptionKey: ""
+    # Token storage database path
+    tokenStorageDb: "/app/data/tokens.db"
+    # OAuth client credentials (optional - uses Dynamic Client Registration if not provided)
+    # Only needed if enableOfflineAccess: true
+    clientId: ""
+    clientSecret: ""
+    # OAuth scopes to request (space-separated)
+    scopes: "openid profile email offline_access notes:read notes:write calendar:read calendar:write contacts:read contacts:write cookbook:read cookbook:write deck:read deck:write tables:read tables:write files:read files:write sharing:read sharing:write todo:read todo:write"
+    # Use existing secret for multi-user basic auth credentials
+    # If set, tokenEncryptionKey, clientId, and clientSecret above are ignored
+    # Secret should contain keys specified in the *Key fields below
+    # Example:
+    #   kubectl create secret generic my-multiuser-creds \
+    #     --from-literal=token_encryption_key=ESF1BvEQ... \
+    #     --from-literal=client_id=my-client-id \
+    #     --from-literal=client_secret=my-client-secret
+    existingSecret: ""
+    # Keys in the existing secret
+    tokenEncryptionKeyKey: "token_encryption_key"
+    clientIdKey: "client_id"
+    clientSecretKey: "client_secret"
+    # Persistent storage for token database
+    persistence:
+      enabled: true
+      # Storage class (leave empty for default)
+      storageClass: ""
+      accessMode: ReadWriteOnce
+      size: 100Mi
+      # Use existing PVC
+      existingClaim: ""
+
   # OAuth2/OIDC settings (experimental)
   oauth:
     # OAuth token type: "jwt" or "opaque"

docker-compose.ci.yml

@@ -0,0 +1,25 @@
+# CI-specific overrides for RAG evaluation pipeline
+# This file is used by the rag-evaluation.yml workflow to configure the MCP
+# container with OpenAI/GitHub Models API for vector embeddings.
+#
+# Usage:
+#   docker compose -f docker-compose.yml -f docker-compose.ci.yml up
+#
+# Environment variables (set in CI workflow):
+#   OPENAI_API_KEY - API key for embeddings (GitHub Models uses GITHUB_TOKEN)
+#   OPENAI_BASE_URL - API endpoint (e.g., https://models.github.ai/inference)
+#   OPENAI_EMBEDDING_MODEL - Model name (e.g., openai/text-embedding-3-small)
+#   OPENAI_GENERATION_MODEL - Model name for generation (e.g., openai/gpt-4o-mini)
+
+services:
+  mcp:
+    environment:
+      # OpenAI provider configuration (required for CI vector sync)
+      - OPENAI_API_KEY=${OPENAI_API_KEY}
+      - OPENAI_BASE_URL=${OPENAI_BASE_URL:-https://models.github.ai/inference}
+      - OPENAI_EMBEDDING_MODEL=${OPENAI_EMBEDDING_MODEL:-openai/text-embedding-3-small}
+      - OPENAI_GENERATION_MODEL=${OPENAI_GENERATION_MODEL:-openai/gpt-4o-mini}
+      # Faster sync for CI
+      - VECTOR_SYNC_SCAN_INTERVAL=${VECTOR_SYNC_SCAN_INTERVAL:-5}
+      # Enable document processing for PDF parsing
+      - ENABLE_DOCUMENT_PROCESSING=true

docker-compose.yml

@@ -21,7 +21,7 @@ services:
     restart: always
 
   app:
-    image: docker.io/library/nextcloud:32.0.2@sha256:ac08482d73ffd85d94069ba291bbd5fb39a70ff21502030a2e3e2d89a7246a48
+    image: docker.io/library/nextcloud:32.0.3@sha256:53231a9fb9233af2c15bfe70fc03ebe639fd53243fa42a9369884b1e0008deae
     restart: always
     ports:
       - 0.0.0.0:8080:80
@@ -34,7 +34,8 @@ services:
       - ./app-hooks:/docker-entrypoint-hooks.d:ro
       # Mount OIDC development directory outside /var/www/html to avoid rsync conflicts
       # The post-installation hook will register /opt/apps as an additional app directory
-      - ./third_party:/opt/apps:ro
+      #- ./third_party:/opt/apps:ro
+      - ./third_party/astrolabe:/opt/apps/astrolabe:ro
     environment:
       - NEXTCLOUD_TRUSTED_DOMAINS=app
       - NEXTCLOUD_ADMIN_USER=admin
@@ -51,7 +52,7 @@ services:
       retries: 30
 
   recipes:
-    image: docker.io/library/nginx:alpine@sha256:b3c656d55d7ad751196f21b7fd2e8d4da9cb430e32f646adcf92441b72f82b14
+    image: docker.io/library/nginx:alpine@sha256:052b75ab72f690f33debaa51c7e08d9b969a0447a133eb2b99cc905d9188cb2b
     restart: always
     volumes:
       - ./tests/fixtures/test_recipe.html:/usr/share/nginx/html/test_recipe.html:ro
@@ -86,7 +87,7 @@ services:
       - NEXTCLOUD_PUBLIC_ISSUER_URL=http://localhost:8080
 
       # Vector sync configuration (ADR-007)
-      - VECTOR_SYNC_ENABLED=true
+      #- VECTOR_SYNC_ENABLED=true
       - VECTOR_SYNC_SCAN_INTERVAL=60
       - VECTOR_SYNC_PROCESSOR_WORKERS=1
 
@@ -122,6 +123,41 @@ services:
       # - DOCUMENT_CHUNK_SIZE=512      # Words per chunk (default: 512)
       # - DOCUMENT_CHUNK_OVERLAP=50    # Overlapping words (default: 50, recommended: 10-20% of chunk size)
 
+  mcp-multi-user-basic:
+    build: .
+    restart: always
+    command: ["--transport", "streamable-http"]
+    depends_on:
+      app:
+        condition: service_healthy
+    ports:
+      - 127.0.0.1:8003:8000
+    environment:
+      # Multi-user BasicAuth pass-through mode (ADR-020)
+      - NEXTCLOUD_HOST=http://app:80
+      - NEXTCLOUD_MCP_SERVER_URL=http://localhost:8003
+      - NEXTCLOUD_PUBLIC_ISSUER_URL=http://localhost:8080
+      - ENABLE_MULTI_USER_BASIC_AUTH=true
+      - ENABLE_OFFLINE_ACCESS=true
+      - ENABLE_BACKGROUND_OPERATIONS=true
+
+      # Token storage (required for middleware initialization)
+      - TOKEN_ENCRYPTION_KEY=ESF1BvEQdGYsCluwMx9Cxvw3uh5pFowPH7Rg_nIliyo=
+      - TOKEN_STORAGE_DB=/app/data/tokens.db
+
+      - VECTOR_SYNC_ENABLED=true
+      - VECTOR_SYNC_SCAN_INTERVAL=60
+      - VECTOR_SYNC_PROCESSOR_WORKERS=1
+
+      # OAuth credentials for background sync (optional - uses DCR if not provided)
+      # Uncomment to avoid DCR:
+      # - NEXTCLOUD_OIDC_CLIENT_ID=your_client_id
+      # - NEXTCLOUD_OIDC_CLIENT_SECRET=your_client_secret
+
+      # NO admin credentials - credentials come from client Authorization header
+    volumes:
+      - multi-user-basic-data:/app/data
+
   mcp-oauth:
     build: .
     command: ["--transport", "streamable-http", "--oauth", "--port", "8001", "--oauth-token-type", "jwt"]
@@ -150,6 +186,19 @@ services:
       # Tokens must contain BOTH MCP and Nextcloud audiences
       # No token exchange needed - tokens work for both MCP auth and Nextcloud APIs
 
+      # Vector sync configuration (ADR-007)
+      - VECTOR_SYNC_ENABLED=true
+      - VECTOR_SYNC_SCAN_INTERVAL=60
+      - VECTOR_SYNC_PROCESSOR_WORKERS=1
+
+      # Qdrant configuration - persistent local storage
+      - QDRANT_LOCATION=/app/data/qdrant
+
+      # Embedding provider for vector sync (use Simple provider as fallback)
+      # Ollama not available in CI/test environments
+      # - OLLAMA_BASE_URL=http://ollama:11434
+      # - OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+
       # NO admin credentials - using OAuth with Dynamic Client Registration (DCR)
       # Client credentials registered via RFC 7591 and stored in volume
       # JWT token type is used for testing (faster validation, scopes embedded in token)
@@ -158,7 +207,7 @@ services:
       - oauth-tokens:/app/data
 
   keycloak:
-    image: quay.io/keycloak/keycloak:26.4.5@sha256:653852bfdea2be6e958b9e90a976eff1c6de34edd55f2f679bdc48ef16bc528e
+    image: quay.io/keycloak/keycloak:26.4.7@sha256:9409c59bdfb65dbffa20b11e6f18b8abb9281d480c7ca402f51ed3d5977e6007
     command:
       - "start-dev"
       - "--import-realm"
@@ -245,7 +294,7 @@ services:
       - smithery
 
   qdrant:
-    image: qdrant/qdrant:v1.16.0@sha256:1005201498cf927d835383d0f918b17d8c9da7db58550f169f694455e42d78f4
+    image: qdrant/qdrant:v1.16.2@sha256:dab6de32f7b2cc599985a7c764db3e8b062f70508fb85ca074aa856f829bf335
     restart: always
     ports:
       - 127.0.0.1:6333:6333  # REST API
@@ -271,3 +320,4 @@ volumes:
   keycloak-oauth-storage:
   qdrant-data:
   mcp-data:
+  multi-user-basic-data:

docs/ADR-017-mcp-tool-annotations.md

@@ -0,0 +1,506 @@
+# ADR-017: Add MCP Tool Annotations for Enhanced Client UX
+
+## Status
+
+Implemented
+
+## Context
+
+The MCP Python SDK supports tool annotations that provide behavioral hints and improved UX to MCP clients. Currently, our 101 tools across 10 modules lack these annotations, resulting in:
+
+- Snake_case function names displayed to users (e.g., "nc_notes_create_note" instead of "Create Note")
+- No behavioral hints for clients about read-only, destructive, or idempotent operations
+- Missing parameter descriptions for better auto-completion and inline help
+- Clients cannot optimize caching, warn before destructive operations, or retry safely
+
+### Available MCP Annotations
+
+The MCP SDK provides three types of annotations:
+
+#### 1. Tool Decorator Parameters
+```python
+@mcp.tool(
+    title="Human-Readable Name",
+    description="Tool description",  # Can also come from docstring
+    annotations=ToolAnnotations(...),
+    icons=[Icon(...)]  # Optional visual icons
+)
+```
+
+#### 2. ToolAnnotations Behavioral Hints
+```python
+from mcp.types import ToolAnnotations
+
+ToolAnnotations(
+    title="Alternative Title",  # Decorator title takes precedence
+    readOnlyHint=True,         # Tool doesn't modify data
+    destructiveHint=True,       # Tool may delete/overwrite data
+    idempotentHint=True,        # Repeated calls with same args are safe
+    openWorldHint=True          # Interacts with external entities
+)
+```
+
+#### 3. Parameter Descriptions
+```python
+from pydantic import Field
+
+async def tool(
+    param: str = Field(description="What this parameter does"),
+    ctx: Context
+):
+```
+
+### Idempotency Analysis
+
+**Important**: Idempotency means calling with **the same inputs** produces the same result.
+
+**NOT Idempotent** (different inputs each call):
+- **Updates with etag**: `update_note(id=1, title="X", etag="abc")` → etag changes to "def"
+  - Second call: `update_note(id=1, title="X", etag="abc")` → fails (etag mismatch)
+  - Different input (stale etag) → different result (error)
+- **Creates**: `create_note(title="X")` → creates note 1
+  - Second call → creates note 2 (different result)
+- **Append operations**: `append_content(id=1, text="X")` → adds X once
+  - Second call → adds X again (different result)
+
+**Idempotent**:
+- **Deletes**: `delete_note(id=1)` → note deleted
+  - Second call → 404 or success (same end state: note doesn't exist)
+  - Note: May return different status code, but end state is identical
+- **Full resource PUT without version control**: `write_file(path="/test.txt", content="Hello")` → file has "Hello"
+  - Second call → file still has "Hello" (same end state)
+  - Example: `nc_webdav_write_file` uses HTTP PUT without etags/version control
+- **Set operations**: `set_property(id=1, value="X")` → property = X
+  - Second call → property still = X (same result)
+  - Note: Nextcloud updates with etags use version control, so not idempotent
+
+**Read-Only** (always idempotent, never destructive):
+- All list, search, get operations
+
+## Decision
+
+Add annotations to all 101 tools in three phases:
+
+### Phase 1: Titles (Quick Win)
+Add human-readable titles to all tools:
+
+```python
+@mcp.tool(title="Create Note")
+async def nc_notes_create_note(...):
+```
+
+**Effort**: 2-3 hours
+**Impact**: Immediate UX improvement
+
+### Phase 2: ToolAnnotations (Behavioral Hints)
+Add annotations based on corrected categorization:
+
+```python
+# Read-only tools
+@mcp.tool(
+    title="Search Notes",
+    annotations=ToolAnnotations(
+        readOnlyHint=True,
+        openWorldHint=True  # Nextcloud is external to MCP server
+    )
+)
+
+# Delete tools (idempotent: same end state)
+@mcp.tool(
+    title="Delete Note",
+    annotations=ToolAnnotations(
+        destructiveHint=True,
+        idempotentHint=True,  # Deleting deleted item = same end state
+        openWorldHint=True
+    )
+)
+
+# Create tools (not idempotent: creates multiple items)
+@mcp.tool(
+    title="Create Note",
+    annotations=ToolAnnotations(
+        idempotentHint=False,
+        openWorldHint=True
+    )
+)
+
+# Update tools with etag (not idempotent: etag changes)
+@mcp.tool(
+    title="Update Note",
+    annotations=ToolAnnotations(
+        idempotentHint=False,  # Etag required = different inputs each time
+        openWorldHint=True
+    )
+)
+
+# Append operations (not idempotent: adds content each time)
+@mcp.tool(
+    title="Append to Note",
+    annotations=ToolAnnotations(
+        idempotentHint=False,
+        openWorldHint=True
+    )
+)
+```
+
+**Effort**: 4-6 hours
+**Impact**: Better client behavior (caching, warnings, retry logic)
+
+### Phase 3: Parameter Descriptions
+Add Field() descriptions to parameters:
+
+```python
+from pydantic import Field
+
+@mcp.tool(title="Create Note", annotations=ToolAnnotations(idempotentHint=False))
+async def nc_notes_create_note(
+    title: str = Field(description="The title of the note"),
+    content: str = Field(description="Markdown content of the note"),
+    category: str = Field(description="Category or folder name for organizing"),
+    ctx: Context
+) -> CreateNoteResponse:
+```
+
+**Effort**: 6-8 hours
+**Impact**: Better auto-completion and inline help
+
+## Tool Categorization
+
+### Read-Only Tools (~40 tools)
+**Pattern**: List, search, get operations
+**Annotations**: `readOnlyHint=True`, `openWorldHint=True`
+
+Examples:
+- `nc_notes_search_notes` → "Search Notes"
+- `nc_webdav_list_directory` → "List Files and Directories"
+- `nc_calendar_list_calendars` → "List Calendars"
+- `nc_contacts_get_contact` → "Get Contact"
+- `nc_semantic_search` → "Semantic Search"
+- `check_logged_in` → "Check Server Login Status"
+
+### Create Tools (~20 tools)
+**Pattern**: Create new resources
+**Annotations**: `idempotentHint=False`, `openWorldHint=True`
+
+Examples:
+- `nc_notes_create_note` → "Create Note"
+- `nc_calendar_create_event` → "Create Calendar Event"
+- `nc_contacts_create_contact` → "Create Contact"
+- `deck_create_card` → "Create Kanban Card"
+- `nc_tables_create_row` → "Create Table Row"
+
+### Update Tools (~25 tools)
+**Pattern**: Modify existing resources with etag
+**Annotations**: `idempotentHint=False` (etag changes), `openWorldHint=True`
+
+Examples:
+- `nc_notes_update_note` → "Update Note"
+- `nc_calendar_update_event` → "Update Calendar Event"
+- `nc_contacts_update_contact` → "Update Contact"
+- `deck_update_card` → "Update Kanban Card"
+
+**Rationale**: Updates require etag, which changes after each update. Same parameters on second call will fail due to stale etag = NOT idempotent.
+
+### Append/Accumulate Tools (~5 tools)
+**Pattern**: Add content without replacing
+**Annotations**: `idempotentHint=False`, `openWorldHint=True`
+
+Examples:
+- `nc_notes_append_content` → "Append to Note"
+
+**Rationale**: Each call adds content, changing the result = NOT idempotent.
+
+### Delete Tools (~10 tools)
+**Pattern**: Remove resources
+**Annotations**: `destructiveHint=True`, `idempotentHint=True`, `openWorldHint=True`
+
+Examples:
+- `nc_notes_delete_note` → "Delete Note"
+- `nc_webdav_delete_resource` → "Delete File or Directory"
+- `nc_calendar_delete_event` → "Delete Calendar Event"
+- `nc_contacts_delete_contact` → "Delete Contact"
+
+**Rationale**: Deleting already-deleted item results in same end state (item doesn't exist) = idempotent. Status code may differ, but outcome is identical.
+
+### Special Cases
+
+#### OAuth Provisioning Tools
+```python
+# Not read-only but requires user interaction
+@mcp.tool(
+    title="Grant Server Access to Nextcloud",
+    annotations=ToolAnnotations(
+        readOnlyHint=False,
+        idempotentHint=False,  # Creates new OAuth session each time
+        openWorldHint=True
+    )
+)
+async def provision_nextcloud_access(ctx: Context):
+```
+
+#### Semantic Search (Closed World)
+```python
+@mcp.tool(
+    title="Semantic Search",
+    annotations=ToolAnnotations(
+        readOnlyHint=True,
+        openWorldHint=False  # Searches only indexed Nextcloud data
+    )
+)
+async def nc_semantic_search(query: str, ctx: Context):
+```
+
+**Rationale**: Semantic search only queries pre-indexed Nextcloud content, not the "open world" like web search would.
+
+## Tool Priority Matrix
+
+### Critical Priority (~2 tools)
+OAuth tools required for server functionality:
+- `provision_nextcloud_access` → "Grant Server Access to Nextcloud"
+- `check_logged_in` → "Check Server Login Status"
+
+### High Priority (~50 tools)
+Most commonly used modules:
+- **Notes** (14 tools): Create, read, update, delete notes
+- **WebDAV** (13 tools): File operations
+- **Calendar** (15 tools): Events and todos
+- **Semantic Search** (6 tools): AI-powered search
+- **Contacts** (9 tools): Address book operations
+
+### Medium Priority (~35 tools)
+Secondary functionality:
+- **Deck** (9 tools): Kanban boards
+- **Tables** (7 tools): Structured data
+- **Sharing** (5 tools): File sharing
+
+### Low Priority (~14 tools)
+Less frequently used:
+- **Cookbook** (8 tools): Recipe management
+- **News** (6 tools): RSS feeds
+
+## Implementation Plan
+
+### Week 1: Phase 1 - Titles
+- Add human-readable titles to all 101 tools
+- Update tool name mapping in documentation
+- Manual test in MCP inspector
+
+### Week 2: Phase 2 - ToolAnnotations (High Priority)
+- Add annotations to Critical and High priority tools (~52 tools)
+- Focus on Notes, WebDAV, Calendar, Semantic, OAuth
+- Add unit tests validating annotation presence
+
+### Week 3: Phase 2 - ToolAnnotations (Medium/Low Priority)
+- Complete remaining tools (~49 tools)
+- Deck, Tables, Contacts, Cookbook, News
+- Update tool listings in README
+
+### Week 4: Phase 3 - Parameter Descriptions
+- Add Field() descriptions to Critical/High priority tools
+- Start with OAuth, Notes, WebDAV modules
+- Incremental completion over time
+
+## Benefits
+
+### For Users
+- **Clearer UI**: "Create Note" vs "nc_notes_create_note"
+- **Safety**: Warnings before destructive operations
+- **Better help**: Parameter descriptions in auto-completion
+- **Confidence**: Know which operations are safe to retry
+
+### For MCP Clients
+- **Caching**: Cache results from read-only tools
+- **Safety prompts**: Warn before destructiveHint=true
+- **Retry logic**: Safely retry idempotent operations
+- **UI organization**: Group by behavior (reads vs writes vs deletes)
+- **Performance**: Optimize based on hints
+
+### For Developers
+- **Self-documenting**: Behavior is explicit
+- **Consistency**: Standard patterns across codebase
+- **Testing**: Validate annotations match implementation
+- **Maintenance**: Clear expectations for new tools
+
+## Consequences
+
+### Positive
+- Immediate UX improvement with minimal effort
+- Clients can make smarter decisions
+- Self-documenting code
+- Follows MCP best practices
+
+### Negative
+- Initial effort to add annotations (12-15 hours total)
+- Must maintain annotations when adding new tools
+- Risk of incorrect annotations misleading clients
+
+### Neutral
+- Annotations are hints, not guarantees
+- Clients may ignore annotations
+- Backward compatible (additive change)
+
+### Mitigations
+- **Incorrect annotations**: Add tests validating behavior matches hints
+- **Maintenance burden**: Add to code review checklist and tool template
+- **Documentation**: Update CLAUDE.md with annotation guidelines
+
+## Examples
+
+### Complete Annotated Tool (Delete)
+
+```python
+from mcp.types import ToolAnnotations
+from pydantic import Field
+
+@mcp.tool(
+    title="Delete Note",
+    annotations=ToolAnnotations(
+        destructiveHint=True,   # Deletes data permanently
+        idempotentHint=True,    # Same end state (note doesn't exist)
+        openWorldHint=True      # Nextcloud is external
+    )
+)
+@require_scopes("notes:write")
+@instrument_tool
+async def nc_notes_delete_note(
+    note_id: int = Field(description="The ID of the note to delete permanently"),
+    ctx: Context
+) -> DeleteNoteResponse:
+    """Delete a note permanently (requires notes:write scope)"""
+    client = await get_client(ctx)
+    # ... implementation ...
+```
+
+### Complete Annotated Tool (Update)
+
+```python
+@mcp.tool(
+    title="Update Note",
+    annotations=ToolAnnotations(
+        idempotentHint=False,   # NOT idempotent: etag changes each update
+        openWorldHint=True
+    )
+)
+@require_scopes("notes:write")
+@instrument_tool
+async def nc_notes_update_note(
+    note_id: int = Field(description="The ID of the note to update"),
+    title: str | None = Field(
+        default=None,
+        description="New title (omit to keep current)"
+    ),
+    content: str | None = Field(
+        default=None,
+        description="New markdown content (omit to keep current)"
+    ),
+    category: str | None = Field(
+        default=None,
+        description="New category/folder (omit to keep current)"
+    ),
+    etag: str = Field(
+        description="ETag from get_note (prevents concurrent modification)"
+    ),
+    ctx: Context
+) -> UpdateNoteResponse:
+    """Update an existing note's title, content, or category.
+
+    The etag parameter is required to prevent overwriting concurrent changes.
+    Get the current ETag by first calling nc_notes_get_note.
+    If the note has been modified since you retrieved it, the update will fail.
+    """
+    client = await get_client(ctx)
+    # ... implementation ...
+```
+
+### Complete Annotated Tool (Read-Only)
+
+```python
+@mcp.tool(
+    title="Search Notes",
+    annotations=ToolAnnotations(
+        readOnlyHint=True,    # Doesn't modify data
+        openWorldHint=True    # Queries Nextcloud
+    )
+)
+@require_scopes("notes:read")
+@instrument_tool
+async def nc_notes_search_notes(
+    query: str = Field(description="Search term to match in note titles or content"),
+    ctx: Context
+) -> SearchNotesResponse:
+    """Search notes by title or content, returning id, title, and category.
+
+    This is a read-only operation that searches across all user notes.
+    Use nc_notes_get_note to retrieve the full content of matching notes.
+    """
+    client = await get_client(ctx)
+    # ... implementation ...
+```
+
+## Testing Strategy
+
+### Unit Tests
+Add tests validating annotation presence and correctness:
+
+```python
+def test_notes_tools_have_annotations():
+    """Verify all notes tools have appropriate annotations."""
+    tools = get_registered_tools(mcp)
+
+    # Check create tool
+    create_tool = tools["nc_notes_create_note"]
+    assert create_tool.title == "Create Note"
+    assert create_tool.annotations.idempotentHint is False
+
+    # Check delete tool
+    delete_tool = tools["nc_notes_delete_note"]
+    assert delete_tool.title == "Delete Note"
+    assert delete_tool.annotations.destructiveHint is True
+    assert delete_tool.annotations.idempotentHint is True
+
+    # Check read-only tool
+    search_tool = tools["nc_notes_search_notes"]
+    assert search_tool.title == "Search Notes"
+    assert search_tool.annotations.readOnlyHint is True
+```
+
+### Integration Tests
+- Verify existing tests pass with annotations
+- Manual testing in MCP inspector/client
+
+### Documentation Updates
+- Update README tool listings with new titles
+- Add annotation guidelines to CLAUDE.md
+- Include examples in developer documentation
+
+## Resolved Questions
+
+1. **WebDAV write_file idempotency** (Resolved: 2025-12-11)
+   - **Decision**: Mark as `idempotentHint=True`
+   - **Rationale**: Uses HTTP PUT without version control. Writing same content to same path repeatedly produces identical end state, which is the definition of idempotency in HTTP semantics.
+
+2. **Semantic search openWorldHint** (Resolved: 2025-12-11)
+   - **Decision**: Mark as `openWorldHint=True`
+   - **Rationale**: For consistency with other Nextcloud tools. While the data being searched is "indexed/internal", Nextcloud itself is external to the MCP server. The fact that data is indexed is an implementation detail, not a fundamental difference from other Nextcloud queries.
+
+3. **Read-only with side effects**: Should tools that log analytics still be readOnlyHint=true?
+   - **Decision**: Yes. Logging/analytics are non-visible side effects that don't change user-observable state. Read-only refers to data modifications that affect the user's content.
+
+## Future Considerations
+
+1. **Icons**: Visual icons for tools (requires design work, deferred to future ADR)
+2. **Parameter descriptions**: Add Pydantic `Field(description=...)` for better auto-completion (Phase 3, future work)
+
+## References
+
+- MCP Python SDK: `/home/chris/Software/python-sdk/`
+- ToolAnnotations spec: `src/mcp/types.py:1247`
+- FastMCP decorator: `src/mcp/server/fastmcp/server.py:444`
+- Examples: `examples/fastmcp/parameter_descriptions.py`, `examples/fastmcp/icons_demo.py`
+
+## Decision Timeline
+
+- **Proposed**: 2025-12-11
+- **Reviewed**: 2025-12-11 (Self-review during implementation)
+- **Accepted**: 2025-12-11
+- **Implemented**: 2025-12-11 (Phase 1 & 2 complete)

docs/ADR-020-deployment-modes-and-configuration-validation.md

@@ -0,0 +1,342 @@
+# ADR-020: Deployment Modes and Configuration Validation
+
+**Status:** Accepted
+**Date:** 2025-12-20
+**Deciders:** Development Team
+**Related:** ADR-002 (Vector Sync), ADR-004 (Progressive Consent), ADR-019 (Multi-user BasicAuth)
+
+## Context
+
+The MCP server supports multiple deployment scenarios with different authentication methods, storage backends, and feature sets. Over time, the configuration system evolved to support ~500+ possible combinations across deployment modes, authentication patterns, and feature toggles. This complexity made it difficult to:
+
+1. Understand what configuration is required for a given deployment
+2. Debug configuration errors (validation scattered across multiple files)
+3. Provide helpful error messages when configuration is invalid
+4. Maintain clear boundaries between deployment modes
+
+**Problems Identified:**
+- No single source of truth for "what config is required for mode X"
+- Validation happening at 4+ different points (Settings.__post_init__, setup_oauth_config(), context helpers, starlette_lifespan)
+- Startup sequence unclear (OAuth setup before FastMCP creation, sync initialization errors)
+- Error messages generic ("X is required") without explaining which deployment mode triggered the requirement
+- Multiple overlapping decision trees (deployment mode, auth mode, features)
+
+## Decision
+
+We formalize five distinct deployment modes with explicit configuration requirements and implement centralized configuration validation.
+
+### Deployment Modes
+
+#### 1. Single-User BasicAuth
+
+**Use Case:** Personal Nextcloud instance, local development
+
+**Required Configuration:**
+```bash
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password  # Or app password
+```
+
+**Optional Configuration:**
+```bash
+# Vector sync (semantic search)
+VECTOR_SYNC_ENABLED=true
+QDRANT_LOCATION=/path/to/qdrant  # Or QDRANT_URL for remote
+
+# Embeddings (optional - Simple provider used as fallback)
+OLLAMA_BASE_URL=http://localhost:11434
+OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+
+# Document processing
+DOCUMENT_CHUNK_SIZE=512
+DOCUMENT_CHUNK_OVERLAP=50
+```
+
+**Characteristics:**
+- Single shared NextcloudClient created at startup
+- No OAuth infrastructure needed
+- No multi-user support
+- Vector sync runs as single-user background task
+- Admin UI available at /app
+
+---
+
+#### 2. Multi-User BasicAuth Pass-Through
+
+**Use Case:** Internal deployment where users provide their own credentials, no background sync needed
+
+**Required Configuration:**
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+ENABLE_MULTI_USER_BASIC_AUTH=true
+```
+
+**Optional Configuration:**
+```bash
+# For background sync (requires app passwords from Astrolabe)
+ENABLE_OFFLINE_ACCESS=true
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+NEXTCLOUD_OIDC_CLIENT_ID=<client-id>
+NEXTCLOUD_OIDC_CLIENT_SECRET=<client-secret>
+VECTOR_SYNC_ENABLED=true
+# ... plus Qdrant and embedding config
+```
+
+**Conditional Requirements:**
+- If `ENABLE_OFFLINE_ACCESS=true`: requires `NEXTCLOUD_OIDC_CLIENT_ID`, `NEXTCLOUD_OIDC_CLIENT_SECRET`, `TOKEN_ENCRYPTION_KEY`, `TOKEN_STORAGE_DB`
+- If `VECTOR_SYNC_ENABLED=true`: requires `ENABLE_OFFLINE_ACCESS=true`
+
+**Characteristics:**
+- No OAuth for client authentication (uses BasicAuth in request headers)
+- BasicAuthMiddleware extracts credentials from Authorization header
+- Client created per-request from extracted credentials
+- Optional: Background sync using app passwords (via Astrolabe API)
+- Admin UI available at /app
+
+---
+
+#### 3. OAuth Single-Audience (Default)
+
+**Use Case:** Multi-user deployment with OAuth authentication, tokens work for both MCP and Nextcloud
+
+**Required Configuration:**
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+# No NEXTCLOUD_USERNAME/PASSWORD (triggers OAuth mode)
+```
+
+**Auto-Configured:**
+- OIDC discovery URL: `{NEXTCLOUD_HOST}/.well-known/openid-configuration`
+- Client credentials: Dynamic Client Registration (DCR) if available
+- Token storage: SQLite at `~/.oauth/clients.db`
+
+**Optional Configuration:**
+```bash
+# Static client credentials (instead of DCR)
+NEXTCLOUD_OIDC_CLIENT_ID=<client-id>
+NEXTCLOUD_OIDC_CLIENT_SECRET=<client-secret>
+
+# Offline access for background sync
+ENABLE_OFFLINE_ACCESS=true
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+VECTOR_SYNC_ENABLED=true
+# ... plus Qdrant and embedding config
+
+# Scopes
+NEXTCLOUD_OIDC_SCOPES="openid profile email notes:read notes:write ..."
+```
+
+**Conditional Requirements:**
+- If `ENABLE_OFFLINE_ACCESS=true`: requires `TOKEN_ENCRYPTION_KEY`, `TOKEN_STORAGE_DB`
+- If `VECTOR_SYNC_ENABLED=true`: requires `ENABLE_OFFLINE_ACCESS=true`
+
+**Characteristics:**
+- Tokens contain both `aud: ["mcp-server", "nextcloud"]`
+- Pass token through to Nextcloud APIs (no exchange)
+- Client created per-request from token in Authorization header
+- Background sync uses refresh tokens (if offline_access enabled)
+- Admin UI available at /app
+
+---
+
+#### 4. OAuth Token Exchange (RFC 8693)
+
+**Use Case:** Multi-user deployment where MCP token is separate from Nextcloud token
+
+**Required Configuration:**
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+ENABLE_TOKEN_EXCHANGE=true
+# No NEXTCLOUD_USERNAME/PASSWORD (triggers OAuth mode)
+```
+
+**Optional Configuration:**
+- Same as OAuth Single-Audience, plus:
+```bash
+TOKEN_EXCHANGE_CACHE_TTL=300  # Cache exchanged tokens
+```
+
+**Characteristics:**
+- Tokens contain only `aud: "mcp-server"`
+- MCP server exchanges token for Nextcloud token via RFC 8693
+- Exchanged tokens cached per-user
+- Client created per-request using exchanged token
+- Background sync uses refresh tokens (if offline_access enabled)
+
+---
+
+#### 5. Smithery Stateless
+
+**Use Case:** Multi-tenant SaaS deployment via Smithery platform
+
+**Required Configuration:**
+- None! Configuration comes from session URL params: `?nextcloud_url=...&username=...&app_password=...`
+
+**Forbidden Configuration:**
+- Must NOT set: `NEXTCLOUD_HOST`, `NEXTCLOUD_USERNAME`, `NEXTCLOUD_PASSWORD`, `ENABLE_MULTI_USER_BASIC_AUTH`, `ENABLE_TOKEN_EXCHANGE`, `ENABLE_OFFLINE_ACCESS`, `VECTOR_SYNC_ENABLED`, `NEXTCLOUD_OIDC_CLIENT_ID`, `NEXTCLOUD_OIDC_CLIENT_SECRET`
+
+**Characteristics:**
+- No persistent storage (stateless)
+- Client created per-request from session config
+- No vector sync (disabled)
+- No admin UI (no /app routes)
+- No OAuth infrastructure
+
+---
+
+### Configuration Validation
+
+**Implementation:** `nextcloud_mcp_server/config_validators.py`
+
+**Key Functions:**
+```python
+def detect_auth_mode(settings: Settings) -> AuthMode:
+    """Detect authentication mode from configuration.
+
+    Priority (most specific to most general):
+    1. Smithery (explicit flag)
+    2. Token exchange (most specific OAuth mode)
+    3. Multi-user BasicAuth
+    4. Single-user BasicAuth
+    5. OAuth single-audience (default OAuth mode)
+    """
+
+def validate_configuration(settings: Settings) -> tuple[AuthMode, list[str]]:
+    """Validate configuration for detected mode.
+
+    Returns:
+        Tuple of (detected_mode, list_of_errors)
+        Empty list means valid configuration.
+    """
+```
+
+**Validation Rules:**
+- **Required variables:** Must be set and non-empty
+- **Forbidden variables:** Must NOT be set (or must be False for booleans)
+- **Conditional requirements:** If feature X is enabled, requires variables Y and Z
+
+**Error Messages:**
+```
+Configuration validation failed for {mode} mode:
+  - [{mode}] Missing required configuration: NEXTCLOUD_HOST
+  - [{mode}] ENABLE_OFFLINE_ACCESS must be enabled when VECTOR_SYNC_ENABLED is true
+
+Mode: {mode}
+Description: {mode_description}
+
+Required configuration:
+  - VAR1
+  - VAR2
+
+Optional configuration:
+  - VAR3
+  - VAR4
+
+Conditional requirements:
+  When FEATURE is enabled:
+    - VAR5
+    - VAR6
+```
+
+**Integration:**
+- Validation runs at app startup in `get_app()` (app.py:1048-1062)
+- All errors reported before any initialization begins
+- Mode-specific error messages explain requirements
+- Validation uses the same Settings object used throughout the app
+
+### Configuration Matrix
+
+| Variable | Single BasicAuth | Multi BasicAuth | OAuth Single | OAuth Exchange | Smithery |
+|----------|------------------|-----------------|--------------|----------------|----------|
+| **NEXTCLOUD_HOST** | Required | Required | Required | Required | Forbidden |
+| **NEXTCLOUD_USERNAME** | Required | Forbidden | Forbidden | Forbidden | Forbidden |
+| **NEXTCLOUD_PASSWORD** | Required | Forbidden | Forbidden | Forbidden | Forbidden |
+| **ENABLE_MULTI_USER_BASIC_AUTH** | Forbidden | Required | Forbidden | Forbidden | Forbidden |
+| **ENABLE_TOKEN_EXCHANGE** | Forbidden | Forbidden | Forbidden | Required | Forbidden |
+| **ENABLE_OFFLINE_ACCESS** | Optional\* | Optional\* | Optional\* | Optional\* | Forbidden |
+| **TOKEN_ENCRYPTION_KEY** | If offline | If offline | If offline | If offline | Forbidden |
+| **TOKEN_STORAGE_DB** | If offline | If offline | If offline | If offline | Forbidden |
+| **OIDC_CLIENT_ID** | Forbidden | If offline | Optional\*\* | Optional\*\* | Forbidden |
+| **OIDC_CLIENT_SECRET** | Forbidden | If offline | Optional\*\* | Optional\*\* | Forbidden |
+| **VECTOR_SYNC_ENABLED** | Optional | Optional | Optional | Optional | Forbidden |
+| **QDRANT_URL/LOCATION** | If vector | If vector | If vector | If vector | Forbidden |
+| **OLLAMA_BASE_URL/OPENAI_API_KEY** | Optional | Optional | Optional | Optional | Forbidden |
+
+\* Only enables background sync for semantic search
+\*\* Uses DCR if not provided
+
+## Consequences
+
+### Positive
+
+1. **Clarity:** Single function to detect mode from config
+2. **Validation:** All config validated upfront with helpful errors
+3. **Debugging:** Clear logs showing "Running in X mode with config Y"
+4. **Maintenance:** Mode-specific logic can be isolated
+5. **Documentation:** Clear mapping of mode → required config
+6. **Error Messages:** Context-aware ("X is required for Y mode")
+7. **Testing:** Each mode testable in isolation
+
+### Negative
+
+1. **Migration:** Existing invalid configurations will now fail at startup
+2. **Flexibility:** Less flexibility in configuration combinations
+3. **Strictness:** Some previously-working combinations may be rejected
+
+### Neutral
+
+1. **Backward Compatibility:** Valid configurations continue to work
+2. **Mode Detection:** Automatic based on config (no explicit mode selection)
+3. **Default Mode:** OAuth single-audience when no credentials provided
+
+## Implementation Notes
+
+### Embedding Provider Validation
+
+Originally, validation required either `OLLAMA_BASE_URL` or `OPENAI_API_KEY` when vector sync was enabled. This was too strict because the Simple provider is always available as a fallback (ADR-015). The validation was removed to allow vector sync without explicit provider configuration.
+
+### Variable Scoping Issues
+
+During implementation, several Python variable scoping issues were discovered in `app.py`:
+- Local variable assignments in `starlette_lifespan()` shadowed outer scope variables
+- Fixed by using unique variable names (e.g., `nextcloud_host_for_context`, `basic_auth_storage`)
+- Removed redundant `settings = get_settings()` call (re-used outer scope)
+
+### Docker Compose Configuration
+
+The `mcp-oauth` service configuration was updated to remove `ENABLE_MULTI_USER_BASIC_AUTH=true` which conflicted with its intended OAuth mode. The service now runs in OAuth single-audience mode with vector sync using the Simple embedding provider as fallback.
+
+## Testing
+
+### Unit Tests
+
+`tests/unit/test_config_validators.py` provides comprehensive coverage:
+- Mode detection with priority ordering (7 tests)
+- Single-user BasicAuth validation (8 tests)
+- Multi-user BasicAuth validation (7 tests)
+- OAuth single-audience validation (6 tests)
+- OAuth token exchange validation (3 tests)
+- Smithery validation (4 tests)
+- Mode summary generation (3 tests)
+- Edge cases (3 tests)
+
+**Total: 41 tests, all passing**
+
+### Integration Tests
+
+Integration tests verify that:
+- Each mode starts successfully with valid configuration
+- Invalid configurations fail with clear error messages
+- Existing deployments continue to work
+
+## References
+
+- [ADR-002: Vector Sync Authentication](ADR-002-vector-sync-authentication.md)
+- [ADR-004: Progressive Consent](ADR-004-progressive-consent.md)
+- [ADR-015: Unified Provider Architecture](ADR-015-unified-provider-architecture.md)
+- [ADR-019: Multi-user BasicAuth Pass-Through](ADR-019-multi-user-basicauth-passthrough.md)
+- Implementation: `nextcloud_mcp_server/config_validators.py`
+- Tests: `tests/unit/test_config_validators.py`

docs/ADR-021-configuration-consolidation.md

@@ -0,0 +1,391 @@
+# ADR-021: Configuration Consolidation and Simplification
+
+**Status:** Accepted
+**Date:** 2025-12-21
+**Deciders:** Development Team
+**Related:** ADR-020 (Deployment Modes), ADR-002 (Vector Sync), ADR-004 (Progressive Consent)
+
+## Context
+
+The configuration system has grown complex with overlapping concerns that make it difficult for users to switch between deployment modes and understand configuration dependencies.
+
+### Problems Identified
+
+1. **Confusing variable names don't reflect purpose**:
+   - `ENABLE_OFFLINE_ACCESS` - Actually controls refresh token storage for background operations, not general "offline" capabilities
+   - `VECTOR_SYNC_ENABLED` - Controls semantic search background indexing (implementation detail, not user-facing feature name)
+   - Users struggle to understand what these variables actually control
+
+2. **Redundant configuration requirements**:
+   - Multi-user semantic search requires setting BOTH `ENABLE_OFFLINE_ACCESS=true` AND `VECTOR_SYNC_ENABLED=true`
+   - The dependency is one-way (semantic search needs background ops, but background ops don't need semantic search)
+   - Users must understand internal implementation details to configure a user-facing feature
+
+3. **Implicit mode detection creates ambiguity**:
+   - Five deployment modes detected via priority-based logic
+   - Users can't easily predict which mode will activate
+   - Configuration errors don't clearly indicate which mode triggered the requirement
+
+4. **OIDC_CLIENT_ID vs NEXTCLOUD_OIDC_CLIENT_ID confusion**:
+   - Investigation revealed these are NOT actually overlapping (`OIDC_CLIENT_ID` is test-only)
+   - However, their similar names create confusion
+
+### Current Configuration Complexity
+
+**Example: Multi-user OAuth with semantic search**:
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_OFFLINE_ACCESS=true      # Why is this needed?
+VECTOR_SYNC_ENABLED=true        # And this separately?
+QDRANT_URL=http://qdrant:6333
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+```
+
+Users must understand:
+- Semantic search requires background token storage (ENABLE_OFFLINE_ACCESS)
+- Background token storage requires encryption keys
+- The relationship between ENABLE_OFFLINE_ACCESS and VECTOR_SYNC_ENABLED
+- Which deployment mode these settings will activate
+
+## Decision
+
+We consolidate overlapping functionality and add explicit mode selection while maintaining 100% backward compatibility.
+
+### 1. Automatic Dependency Resolution
+
+**Make ENABLE_SEMANTIC_SEARCH the primary control** that automatically enables required dependencies:
+
+**New behavior**:
+```python
+@property
+def enable_background_operations(self) -> bool:
+    """Background operations - auto-enabled by semantic search in multi-user modes."""
+    # Check new names first
+    explicit = os.getenv("ENABLE_BACKGROUND_OPERATIONS", "").lower() == "true"
+    # Fall back to old name with deprecation warning
+    legacy = os.getenv("ENABLE_OFFLINE_ACCESS", "").lower() == "true"
+    # Auto-enable if semantic search needs it
+    auto_enabled = self.enable_semantic_search and self.is_multi_user_mode()
+
+    return explicit or legacy or auto_enabled
+
+@property
+def enable_semantic_search(self) -> bool:
+    """Semantic search - renamed from VECTOR_SYNC_ENABLED."""
+    new_value = os.getenv("ENABLE_SEMANTIC_SEARCH", "").lower() == "true"
+    old_value = os.getenv("VECTOR_SYNC_ENABLED", "").lower() == "true"
+    return new_value or old_value
+```
+
+**Result**: Users set `ENABLE_SEMANTIC_SEARCH=true` and the system automatically enables background token storage when needed.
+
+### 2. Explicit Mode Selection (Optional)
+
+Add `MCP_DEPLOYMENT_MODE` environment variable to remove detection ambiguity:
+
+```bash
+# Optional: Explicitly declare deployment mode
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# Valid values: single_user_basic, multi_user_basic,
+#               oauth_single_audience, oauth_token_exchange, smithery
+```
+
+**Detection logic**:
+1. If `MCP_DEPLOYMENT_MODE` is set → validate and use it
+2. Otherwise → use priority-based auto-detection (existing behavior)
+3. Validate explicit mode doesn't conflict with detected mode
+
+### 3. Simplified User Experience
+
+**Before**:
+```bash
+# Multi-user OAuth with semantic search
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_OFFLINE_ACCESS=true      # Confusing
+VECTOR_SYNC_ENABLED=true        # Why both?
+QDRANT_URL=http://qdrant:6333
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+```
+
+**After**:
+```bash
+# Multi-user OAuth with semantic search
+NEXTCLOUD_HOST=https://nextcloud.example.com
+MCP_DEPLOYMENT_MODE=oauth_single_audience  # Explicit (optional)
+ENABLE_SEMANTIC_SEARCH=true                # Auto-enables background ops
+QDRANT_URL=http://qdrant:6333
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+```
+
+**Benefits**:
+- 2 fewer variables to understand/set
+- Clear intent ("I want semantic search")
+- Explicit mode declaration (optional)
+- All existing configs continue working
+
+### 4. Variable Naming Strategy
+
+**Deprecated (but still functional)**:
+- `ENABLE_OFFLINE_ACCESS` → Renamed to `ENABLE_BACKGROUND_OPERATIONS`
+- `VECTOR_SYNC_ENABLED` → Renamed to `ENABLE_SEMANTIC_SEARCH`
+
+**No change needed**:
+- `VECTOR_SYNC_SCAN_INTERVAL` - Implementation tuning parameter (keep as-is)
+- `VECTOR_SYNC_PROCESSOR_WORKERS` - Implementation tuning parameter (keep as-is)
+- `VECTOR_SYNC_QUEUE_MAX_SIZE` - Implementation tuning parameter (keep as-is)
+
+**Rationale**: Only rename user-facing feature flags, not internal tuning parameters.
+
+### 5. Backward Compatibility
+
+**Support both old and new names for minimum 2 major versions**:
+
+```python
+@property
+def enable_semantic_search(self) -> bool:
+    new_value = os.getenv("ENABLE_SEMANTIC_SEARCH", "").lower() == "true"
+    old_value = os.getenv("VECTOR_SYNC_ENABLED", "").lower() == "true"
+
+    if new_value and old_value:
+        logger.warning(
+            "Both ENABLE_SEMANTIC_SEARCH and VECTOR_SYNC_ENABLED are set. "
+            "Using ENABLE_SEMANTIC_SEARCH. VECTOR_SYNC_ENABLED is deprecated."
+        )
+
+    if old_value and not new_value:
+        logger.warning(
+            "VECTOR_SYNC_ENABLED is deprecated. Please use ENABLE_SEMANTIC_SEARCH instead."
+        )
+
+    return new_value or old_value
+```
+
+**Deprecation timeline**:
+- v0.6.0: Add new variables, deprecate old ones (both work with warnings)
+- v1.0.0: Remove old variables (breaking change, well-announced)
+- Minimum 2 major versions of support (12+ months)
+
+## Consequences
+
+### Positive
+
+1. **Reduced cognitive load**: Users set `ENABLE_SEMANTIC_SEARCH=true` instead of understanding internal dependencies
+2. **Clearer intent**: Variable names reflect user-facing features, not implementation details
+3. **Explicit mode control**: `MCP_DEPLOYMENT_MODE` removes detection ambiguity
+4. **Better onboarding**: New users see simpler configuration in env.sample
+5. **Improved error messages**: Validation can suggest "set MCP_DEPLOYMENT_MODE=X" instead of relying on implicit detection
+6. **No breaking changes**: All existing configurations continue working
+
+### Negative
+
+1. **Transition period complexity**: Both old and new names supported for 2+ versions
+2. **Documentation burden**: All docs must be updated to show new approach
+3. **Test coverage expansion**: Must test both old and new variable names in all modes
+4. **Migration effort**: Existing deployments should eventually migrate (optional but recommended)
+
+### Neutral
+
+1. **Same functionality**: No new features, just better organization
+2. **Same validation**: Underlying requirements unchanged (e.g., semantic search still needs Qdrant)
+3. **Same performance**: No runtime performance impact
+
+## Implementation
+
+### Phase 1: Configuration Consolidation (v0.6.0)
+
+**Files to modify**:
+- `nextcloud_mcp_server/config.py` - Add property-based deprecation with auto-enablement
+- `nextcloud_mcp_server/config_validators.py` - Simplify validation (semantic search no longer requires explicit background operations setting)
+- `nextcloud_mcp_server/app.py` - Add informative logging for auto-enablement
+- `tests/unit/test_config_validators.py` - Add auto-enablement tests
+- `docs/configuration-migration-v2.md` - Create migration guide
+
+**Key changes**:
+1. `enable_background_operations` property auto-enables when `enable_semantic_search=true` in multi-user modes
+2. `enable_semantic_search` property accepts both `ENABLE_SEMANTIC_SEARCH` and `VECTOR_SYNC_ENABLED`
+3. Smart logging when auto-enablement occurs or deprecated variables used
+4. Validation simplified to remove redundant requirements
+
+### Phase 2: Explicit Mode Selection (v0.6.0)
+
+**Files to modify**:
+- `nextcloud_mcp_server/config.py` - Add `deployment_mode` field
+- `nextcloud_mcp_server/config_validators.py` - Check explicit mode first, fall back to auto-detection
+- `tests/unit/test_config_validators.py` - Test mode override and conflict detection
+- `docs/configuration.md` - Document mode selection
+
+**Key changes**:
+1. Add `MCP_DEPLOYMENT_MODE` environment variable (optional)
+2. Mode detection checks explicit mode first, then auto-detects
+3. Validate explicit mode doesn't conflict with detected mode
+4. Better error messages referencing explicit mode setting
+
+### Phase 3: env.sample Reorganization (v0.6.0)
+
+**Files to create/modify**:
+- `env.sample` - Reorganize by deployment mode
+- `env.sample.single-user` - Simplest config template
+- `env.sample.oauth-multi-user` - Multi-user template showing consolidation
+- `env.sample.oauth-advanced` - Token exchange mode template
+- `README.md` - Update Quick Start to reference templates
+
+**Key changes**:
+1. Group related settings by deployment mode
+2. Show simplified configuration (only essential variables)
+3. Document automatic dependencies inline
+4. Provide mode-specific quick-start templates
+
+### Phase 4: Documentation Updates (v0.7.0)
+
+**Files to modify**:
+- `docs/configuration.md` - Lead with consolidated approach
+- `docs/authentication.md` - Update mode guidance with `MCP_DEPLOYMENT_MODE`
+- `docs/troubleshooting.md` - Add consolidation troubleshooting section
+- `docs/configuration-migration-v2.md` - Expand with comprehensive examples
+- `docs/ADR-020-deployment-modes-and-configuration-validation.md` - Update configuration matrix
+- All other ADRs - Update variable references
+
+**Key changes**:
+1. Update all examples to use new variable names
+2. Add before/after migration examples
+3. Document automatic dependency resolution
+4. Add mode selection decision tree diagram
+
+## Validation Strategy
+
+### Test Coverage Requirements
+
+**Backward compatibility tests**:
+- Old variable names still work (ENABLE_OFFLINE_ACCESS, VECTOR_SYNC_ENABLED)
+- New variable names work (ENABLE_BACKGROUND_OPERATIONS, ENABLE_SEMANTIC_SEARCH)
+- Setting both old and new triggers deprecation warning but works correctly
+- All 41 existing config validation tests pass
+
+**Auto-enablement tests**:
+- `ENABLE_SEMANTIC_SEARCH=true` in OAuth mode → `enable_background_operations=true`
+- `ENABLE_SEMANTIC_SEARCH=true` in single-user mode → `enable_background_operations=false` (not needed)
+- `ENABLE_SEMANTIC_SEARCH=false` → `enable_background_operations=false` (unless explicitly set)
+
+**Mode selection tests**:
+- `MCP_DEPLOYMENT_MODE=oauth_single_audience` → mode correctly detected
+- `MCP_DEPLOYMENT_MODE` conflicts with detected mode → validation error
+- No `MCP_DEPLOYMENT_MODE` → auto-detection works as before
+
+## Success Metrics
+
+**Immediate** (v0.6.0 release):
+- Zero breaking changes in existing deployments
+- All 41 config validation tests pass
+- New users report clearer configuration process
+
+**Medium-term** (6 months after v0.6.0):
+- 80% of new deployments use new variable names
+- Mode selection errors decrease by 50%
+- Support requests about configuration decrease
+
+**Long-term** (12+ months):
+- 90% of deployments migrated to new names
+- Old variable names can be safely removed in v1.0.0
+- Configuration-related issues in issue tracker decrease
+
+## Alternatives Considered
+
+### Alternative 1: Just Rename Variables
+
+**Rejected**: User feedback: "There's no reason to just rename variables without consolidating functionality"
+
+This would make names clearer but wouldn't reduce the number of variables users need to set. The real problem is requiring users to set both ENABLE_OFFLINE_ACCESS and VECTOR_SYNC_ENABLED when they just want semantic search.
+
+### Alternative 2: Remove ENABLE_OFFLINE_ACCESS Entirely
+
+**Rejected**: Advanced users need background operations without semantic search
+
+Some deployments might want background token storage for future features (background Deck sync, background Calendar sync, etc.) without enabling semantic search. Keeping ENABLE_BACKGROUND_OPERATIONS (renamed) allows this.
+
+### Alternative 3: Always Auto-Enable Background Operations
+
+**Rejected**: Single-user mode doesn't need background token storage
+
+Auto-enablement is only needed in multi-user modes. Single-user mode uses a shared client with BasicAuth, so background token storage is unnecessary. Always enabling it would waste resources and create confusing log messages.
+
+### Alternative 4: Require All New Names Immediately
+
+**Rejected**: Breaking change would affect all existing deployments
+
+Forcing migration to new variable names in v0.6.0 would break every existing deployment. Supporting both old and new names with deprecation warnings provides a smooth migration path.
+
+## References
+
+- [ADR-020: Deployment Modes and Configuration Validation](ADR-020-deployment-modes-and-configuration-validation.md)
+- [ADR-002: Vector Sync Authentication](ADR-002-vector-sync-authentication.md)
+- [ADR-004: Progressive Consent](ADR-004-mcp-application-oauth.md)
+- [Issue: Configuration complexity for multi-user semantic search](https://github.com/cbcoutinho/nextcloud-mcp-server/issues/XXX)
+
+## Migration Examples
+
+### Example 1: Single-User BasicAuth with Semantic Search
+
+**Before**:
+```bash
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+VECTOR_SYNC_ENABLED=true
+QDRANT_LOCATION=:memory:
+```
+
+**After** (optional migration):
+```bash
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+ENABLE_SEMANTIC_SEARCH=true  # Renamed
+QDRANT_LOCATION=:memory:
+# Note: Background operations NOT auto-enabled (not needed in single-user mode)
+```
+
+### Example 2: Multi-User OAuth with Semantic Search
+
+**Before**:
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_OFFLINE_ACCESS=true
+VECTOR_SYNC_ENABLED=true
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+QDRANT_URL=http://qdrant:6333
+```
+
+**After** (simplified):
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+MCP_DEPLOYMENT_MODE=oauth_single_audience  # Explicit (optional)
+ENABLE_SEMANTIC_SEARCH=true                # Auto-enables background operations
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+QDRANT_URL=http://qdrant:6333
+# Note: ENABLE_OFFLINE_ACCESS no longer needed (auto-enabled)
+```
+
+### Example 3: Multi-User OAuth WITHOUT Semantic Search
+
+**Before**:
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_OFFLINE_ACCESS=true  # For future background features
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+```
+
+**After** (optional migration):
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+ENABLE_BACKGROUND_OPERATIONS=true  # Renamed for clarity
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/path/to/tokens.db
+```

docs/MCP-1.23-DNS-REBINDING-FIX.md

@@ -0,0 +1,104 @@
+# MCP 1.23.x DNS Rebinding Protection Fix
+
+## Problem
+
+MCP Python SDK 1.23.0 introduced **automatic DNS rebinding protection** that breaks containerized deployments (Kubernetes, Docker) when the protection is unintentionally auto-enabled.
+
+### Root Cause
+
+From `mcp/server/fastmcp/server.py:177-183` in the Python SDK:
+
+```python
+# Auto-enable DNS rebinding protection for localhost (IPv4 and IPv6)
+if transport_security is None and host in ("127.0.0.1", "localhost", "::1"):
+    transport_security = TransportSecuritySettings(
+        enable_dns_rebinding_protection=True,
+        allowed_hosts=["127.0.0.1:*", "localhost:*", "[::1]:*"],
+        allowed_origins=["http://127.0.0.1:*", "http://localhost:*", "http://[::1]:*"],
+    )
+```
+
+### What Was Happening
+
+1. **FastMCP initialization** in `app.py` didn't pass `host` or `transport_security` parameters
+2. **Defaults applied**: `host="127.0.0.1"`, `transport_security=None`
+3. **Auto-enablement triggered**: Condition `transport_security is None and host == "127.0.0.1"` was TRUE
+4. **Protection activated** with `allowed_hosts=["127.0.0.1:*", "localhost:*", "[::1]:*"]`
+5. **Kubernetes requests rejected**: `Host: nextcloud-mcp-server.default.svc.cluster.local:8000` didn't match allowed hosts
+
+### Why `--host 0.0.0.0` Didn't Help
+
+The `--host` CLI flag (used in Dockerfile/docker-compose) controls **uvicorn's bind address**, NOT the **FastMCP `host` parameter**. These are separate concerns:
+
+- **Uvicorn bind address** (`--host 0.0.0.0`): Where the HTTP server listens
+- **FastMCP host parameter** (defaulted to `"127.0.0.1"`): Used for auto-enablement logic
+
+## Solution
+
+Explicitly disable DNS rebinding protection by passing `transport_security=TransportSecuritySettings(enable_dns_rebinding_protection=False)` to all FastMCP instances.
+
+### Changes Made
+
+Modified `nextcloud_mcp_server/app.py`:
+
+1. **Import** `TransportSecuritySettings` from `mcp.server.transport_security`
+2. **Updated all three FastMCP initializations**:
+   - OAuth mode (line 1015)
+   - Smithery stateless mode (line 1030)
+   - BasicAuth mode (line 1040)
+
+Each now includes:
+```python
+transport_security=TransportSecuritySettings(enable_dns_rebinding_protection=False)
+```
+
+## Impact
+
+### ✅ What This Fixes
+
+- **Kubernetes deployments**: Requests with k8s service DNS names now work
+- **Docker deployments**: Port-mapped requests (localhost:8000 → container) now work
+- **Reverse proxy deployments**: Proxied requests with various Host headers now work
+- **Ingress controllers**: Requests via ingress hostnames now work
+
+### 🔒 Security Considerations
+
+DNS rebinding protection defends against attacks where:
+1. Attacker controls a DNS domain (e.g., `evil.com`)
+2. DNS initially resolves to attacker's IP
+3. After victim's browser caches the origin, DNS changes to victim's localhost
+4. Attacker's page can now make requests to victim's localhost services
+
+**Why it's safe to disable for this deployment:**
+
+1. **OAuth authentication required** in production deployments (ADR-002, ADR-004)
+2. **Network-level isolation** in containerized environments (k8s network policies, Docker networks)
+3. **MCP is server-to-server**, not exposed to browsers (no CORS concerns)
+4. **Host header validation inappropriate** for multi-tenant k8s environments
+
+If DNS rebinding protection is needed for specific deployments, it can be re-enabled with a custom allowed hosts list:
+
+```python
+transport_security=TransportSecuritySettings(
+    enable_dns_rebinding_protection=True,
+    allowed_hosts=[
+        "nextcloud-mcp-server.default.svc.cluster.local:*",
+        "mcp.example.com:*",
+        # Add all your expected Host header values
+    ]
+)
+```
+
+## Testing
+
+- ✅ Ruff linting passes
+- ✅ Type checking passes (pre-existing warnings unrelated)
+- ✅ Module imports successfully
+- ✅ Compatible with MCP 1.23.x
+
+## References
+
+- [MCP Python SDK 1.23.0 Release](https://github.com/modelcontextprotocol/python-sdk/releases/tag/v1.23.0)
+- Commit: `d3a1841` - "Auto-enable DNS rebinding protection for localhost servers"
+- Issue #373 (original report of k8s breakage)
+- PR #382 (MCP 1.23.x upgrade)

docs/configuration-migration-v2.md

@@ -0,0 +1,564 @@
+# Configuration Migration Guide v2
+
+**Version:** v0.58.0
+**Status:** Active
+**Related ADR:** [ADR-021: Configuration Consolidation and Simplification](ADR-021-configuration-consolidation.md)
+
+## Overview
+
+This guide helps you migrate from the old configuration variables to the new consolidated approach introduced in v0.58.0.
+
+**Key Changes:**
+- `VECTOR_SYNC_ENABLED` → `ENABLE_SEMANTIC_SEARCH`
+- `ENABLE_OFFLINE_ACCESS` → `ENABLE_BACKGROUND_OPERATIONS`
+- New: `MCP_DEPLOYMENT_MODE` for explicit mode selection
+- Automatic dependency resolution: semantic search auto-enables background operations
+
+**Backward Compatibility:**
+- Old variable names still work in v0.58.0+
+- Deprecation warnings logged when old names used
+- Old names will be removed in v1.0.0
+
+---
+
+## Quick Reference: Variable Name Changes
+
+| Old Name | New Name | Status |
+|----------|----------|--------|
+| `VECTOR_SYNC_ENABLED` | `ENABLE_SEMANTIC_SEARCH` | Deprecated |
+| `ENABLE_OFFLINE_ACCESS` | `ENABLE_BACKGROUND_OPERATIONS` | Deprecated |
+| N/A (auto-detected) | `MCP_DEPLOYMENT_MODE` | New (optional) |
+
+**Tuning parameters unchanged:**
+- `VECTOR_SYNC_SCAN_INTERVAL` - Keep as-is
+- `VECTOR_SYNC_PROCESSOR_WORKERS` - Keep as-is
+- `VECTOR_SYNC_QUEUE_MAX_SIZE` - Keep as-is
+
+---
+
+## Migration Scenarios
+
+### Scenario 1: Single-User BasicAuth with Semantic Search
+
+**Before (v0.57.x):**
+```bash
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+VECTOR_SYNC_ENABLED=true
+QDRANT_LOCATION=:memory:
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+**After (v0.58.0+):**
+```bash
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+
+# Optional: Explicit mode declaration (recommended)
+MCP_DEPLOYMENT_MODE=single_user_basic
+
+# Updated variable name
+ENABLE_SEMANTIC_SEARCH=true  # Previously VECTOR_SYNC_ENABLED
+
+QDRANT_LOCATION=:memory:
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+**What Changed:**
+- ✅ Renamed `VECTOR_SYNC_ENABLED` to `ENABLE_SEMANTIC_SEARCH`
+- ✅ Added optional `MCP_DEPLOYMENT_MODE` for clarity
+- ✅ Background operations NOT auto-enabled (not needed in single-user mode)
+
+**Migration Steps:**
+1. Replace `VECTOR_SYNC_ENABLED=true` with `ENABLE_SEMANTIC_SEARCH=true`
+2. Optionally add `MCP_DEPLOYMENT_MODE=single_user_basic`
+3. Restart server
+4. Verify deprecation warnings are gone
+
+---
+
+### Scenario 2: Multi-User OAuth with Semantic Search
+
+**Before (v0.57.x):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+NEXTCLOUD_USERNAME=
+NEXTCLOUD_PASSWORD=
+
+# Both variables required - confusing!
+ENABLE_OFFLINE_ACCESS=true
+VECTOR_SYNC_ENABLED=true
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+QDRANT_URL=http://qdrant:6333
+OLLAMA_BASE_URL=http://ollama:11434
+NEXTCLOUD_OIDC_CLIENT_ID=mcp-server
+NEXTCLOUD_OIDC_CLIENT_SECRET=secret
+```
+
+**After (v0.58.0+ - Simplified):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+NEXTCLOUD_USERNAME=
+NEXTCLOUD_PASSWORD=
+
+# Optional: Explicit mode declaration
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# One variable does it all!
+ENABLE_SEMANTIC_SEARCH=true  # Automatically enables background operations
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+QDRANT_URL=http://qdrant:6333
+OLLAMA_BASE_URL=http://ollama:11434
+NEXTCLOUD_OIDC_CLIENT_ID=mcp-server
+NEXTCLOUD_OIDC_CLIENT_SECRET=secret
+
+# Note: ENABLE_OFFLINE_ACCESS no longer needed!
+# Background operations are auto-enabled by ENABLE_SEMANTIC_SEARCH
+```
+
+**What Changed:**
+- ✅ Removed need for explicit `ENABLE_OFFLINE_ACCESS`
+- ✅ `ENABLE_SEMANTIC_SEARCH` automatically enables background operations in multi-user modes
+- ✅ Renamed `VECTOR_SYNC_ENABLED` to `ENABLE_SEMANTIC_SEARCH`
+- ✅ Added optional explicit mode declaration
+
+**Migration Steps:**
+1. Replace `VECTOR_SYNC_ENABLED=true` with `ENABLE_SEMANTIC_SEARCH=true`
+2. Remove `ENABLE_OFFLINE_ACCESS=true` (auto-enabled)
+3. Optionally add `MCP_DEPLOYMENT_MODE=oauth_single_audience`
+4. Restart server
+5. Check logs for confirmation: "Automatically enabled background operations for semantic search"
+
+---
+
+### Scenario 3: Multi-User OAuth WITHOUT Semantic Search
+
+**Before (v0.57.x):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+NEXTCLOUD_USERNAME=
+NEXTCLOUD_PASSWORD=
+
+# Enable background operations for future features
+ENABLE_OFFLINE_ACCESS=true
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+NEXTCLOUD_OIDC_CLIENT_ID=mcp-server
+NEXTCLOUD_OIDC_CLIENT_SECRET=secret
+```
+
+**After (v0.58.0+):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+NEXTCLOUD_USERNAME=
+NEXTCLOUD_PASSWORD=
+
+# Optional: Explicit mode declaration
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# Renamed for clarity
+ENABLE_BACKGROUND_OPERATIONS=true  # Previously ENABLE_OFFLINE_ACCESS
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+NEXTCLOUD_OIDC_CLIENT_ID=mcp-server
+NEXTCLOUD_OIDC_CLIENT_SECRET=secret
+```
+
+**What Changed:**
+- ✅ Renamed `ENABLE_OFFLINE_ACCESS` to `ENABLE_BACKGROUND_OPERATIONS`
+- ✅ Added optional explicit mode declaration
+
+**Migration Steps:**
+1. Replace `ENABLE_OFFLINE_ACCESS=true` with `ENABLE_BACKGROUND_OPERATIONS=true`
+2. Optionally add `MCP_DEPLOYMENT_MODE=oauth_single_audience`
+3. Restart server
+
+---
+
+### Scenario 4: Multi-User BasicAuth with Semantic Search
+
+**Before (v0.57.x):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_MULTI_USER_BASIC_AUTH=true
+
+# Both required - redundant
+ENABLE_OFFLINE_ACCESS=true
+VECTOR_SYNC_ENABLED=true
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+QDRANT_URL=http://qdrant:6333
+OLLAMA_BASE_URL=http://ollama:11434
+NEXTCLOUD_OIDC_CLIENT_ID=mcp-server
+NEXTCLOUD_OIDC_CLIENT_SECRET=secret
+```
+
+**After (v0.58.0+ - Simplified):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_MULTI_USER_BASIC_AUTH=true
+
+# Optional: Explicit mode declaration
+MCP_DEPLOYMENT_MODE=multi_user_basic
+
+# One variable handles both!
+ENABLE_SEMANTIC_SEARCH=true  # Auto-enables background operations
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+QDRANT_URL=http://qdrant:6333
+OLLAMA_BASE_URL=http://ollama:11434
+NEXTCLOUD_OIDC_CLIENT_ID=mcp-server
+NEXTCLOUD_OIDC_CLIENT_SECRET=secret
+
+# Note: ENABLE_OFFLINE_ACCESS no longer needed!
+```
+
+**What Changed:**
+- ✅ Semantic search auto-enables background operations
+- ✅ Removed need for explicit `ENABLE_OFFLINE_ACCESS`
+- ✅ Clearer variable naming
+
+**Migration Steps:**
+1. Replace `VECTOR_SYNC_ENABLED=true` with `ENABLE_SEMANTIC_SEARCH=true`
+2. Remove `ENABLE_OFFLINE_ACCESS=true` (auto-enabled)
+3. Optionally add `MCP_DEPLOYMENT_MODE=multi_user_basic`
+4. Restart server
+
+---
+
+### Scenario 5: Token Exchange Mode with Semantic Search
+
+**Before (v0.57.x):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_TOKEN_EXCHANGE=true
+
+# Both required
+ENABLE_OFFLINE_ACCESS=true
+VECTOR_SYNC_ENABLED=true
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+TOKEN_EXCHANGE_CACHE_TTL=300
+QDRANT_URL=http://qdrant:6333
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+**After (v0.58.0+ - Simplified):**
+```bash
+NEXTCLOUD_HOST=https://nextcloud.example.com
+ENABLE_TOKEN_EXCHANGE=true
+
+# Optional: Explicit mode declaration
+MCP_DEPLOYMENT_MODE=oauth_token_exchange
+
+# One variable!
+ENABLE_SEMANTIC_SEARCH=true  # Auto-enables background operations
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+TOKEN_EXCHANGE_CACHE_TTL=300
+QDRANT_URL=http://qdrant:6333
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+**What Changed:**
+- ✅ Semantic search auto-enables background operations
+- ✅ Explicit mode declaration available
+
+**Migration Steps:**
+1. Replace `VECTOR_SYNC_ENABLED=true` with `ENABLE_SEMANTIC_SEARCH=true`
+2. Remove `ENABLE_OFFLINE_ACCESS=true` (auto-enabled)
+3. Optionally add `MCP_DEPLOYMENT_MODE=oauth_token_exchange`
+4. Restart server
+
+---
+
+## Understanding Automatic Dependency Resolution
+
+### How It Works
+
+In v0.58.0+, the server uses smart dependency resolution:
+
+```python
+# In multi-user modes (OAuth, Multi-User BasicAuth):
+if ENABLE_SEMANTIC_SEARCH == true:
+    background_operations = automatically enabled
+    refresh_tokens = automatically requested
+    token_storage = required (TOKEN_ENCRYPTION_KEY, TOKEN_STORAGE_DB)
+    oauth_credentials = required (for app password retrieval)
+```
+
+**What this means:**
+- ✅ Set `ENABLE_SEMANTIC_SEARCH=true`
+- ✅ Provide required infrastructure (Qdrant, Ollama, encryption key)
+- ✅ System automatically enables background operations
+- ❌ No need to set `ENABLE_BACKGROUND_OPERATIONS` separately
+
+### When Automatic Enablement Happens
+
+| Deployment Mode | Semantic Search Enabled | Background Operations Auto-Enabled? |
+|----------------|------------------------|-----------------------------------|
+| Single-User BasicAuth | ✅ | ❌ No (not needed) |
+| Multi-User BasicAuth | ✅ | ✅ Yes |
+| OAuth Single-Audience | ✅ | ✅ Yes |
+| OAuth Token Exchange | ✅ | ✅ Yes |
+| Smithery Stateless | N/A (not supported) | N/A |
+
+### When to Explicitly Set ENABLE_BACKGROUND_OPERATIONS
+
+Only needed when you want background operations **without** semantic search:
+
+```bash
+# Example: OAuth mode with background operations but NO semantic search
+NEXTCLOUD_HOST=https://nextcloud.example.com
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# Explicitly enable background operations for future features
+ENABLE_BACKGROUND_OPERATIONS=true
+
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+
+# Semantic search disabled
+ENABLE_SEMANTIC_SEARCH=false
+```
+
+---
+
+## Explicit Mode Selection
+
+### Why Use MCP_DEPLOYMENT_MODE?
+
+**Benefits:**
+- ✅ Removes ambiguity about which mode is active
+- ✅ Validation errors reference specific mode requirements
+- ✅ Catches configuration mistakes early
+- ✅ Self-documenting configuration
+
+**Example:**
+```bash
+# Without explicit mode:
+NEXTCLOUD_HOST=https://nextcloud.example.com
+# Is this OAuth or Multi-User BasicAuth? Not immediately clear.
+
+# With explicit mode:
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+NEXTCLOUD_HOST=https://nextcloud.example.com
+# Clear: This is OAuth mode
+```
+
+### Valid Mode Values
+
+| Mode Value | Description |
+|-----------|-------------|
+| `single_user_basic` | Single-user with username/password |
+| `multi_user_basic` | Multi-user with BasicAuth pass-through |
+| `oauth_single_audience` | Multi-user OAuth (recommended) |
+| `oauth_token_exchange` | Multi-user OAuth with token exchange |
+| `smithery` | Smithery platform deployment |
+
+### Mode Detection Priority
+
+When `MCP_DEPLOYMENT_MODE` is set:
+1. ✅ Explicit mode is used
+2. ✅ Server validates configuration matches explicit mode
+3. ❌ Auto-detection is skipped
+
+When `MCP_DEPLOYMENT_MODE` is NOT set:
+1. ✅ Auto-detection runs (existing behavior)
+2. ✅ Priority: Smithery → Token Exchange → Multi-User BasicAuth → Single-User BasicAuth → OAuth Single-Audience
+
+---
+
+## Validation and Error Messages
+
+### Old Validation (v0.57.x)
+
+```
+Error: [multi_user_basic] ENABLE_OFFLINE_ACCESS is required when VECTOR_SYNC_ENABLED is enabled
+```
+
+**Problem:** User must understand internal dependency relationship
+
+### New Validation (v0.58.0+)
+
+```
+Error: [multi_user_basic] TOKEN_ENCRYPTION_KEY is required when ENABLE_SEMANTIC_SEARCH is enabled
+```
+
+**Benefit:** Clear what's needed, no mention of internal ENABLE_BACKGROUND_OPERATIONS flag
+
+---
+
+## Troubleshooting Migration
+
+### Issue: Deprecation Warning After Migration
+
+**Symptom:**
+```
+WARNING: VECTOR_SYNC_ENABLED is deprecated. Please use ENABLE_SEMANTIC_SEARCH instead.
+```
+
+**Solution:**
+1. Check for `VECTOR_SYNC_ENABLED` in `.env` file
+2. Replace with `ENABLE_SEMANTIC_SEARCH`
+3. Search for any scripts/CI configs using old name
+4. Restart server
+
+### Issue: Both Old and New Names Set
+
+**Symptom:**
+```
+WARNING: Both ENABLE_SEMANTIC_SEARCH and VECTOR_SYNC_ENABLED are set. Using ENABLE_SEMANTIC_SEARCH.
+```
+
+**Solution:**
+1. Remove `VECTOR_SYNC_ENABLED` from `.env`
+2. Keep `ENABLE_SEMANTIC_SEARCH`
+3. Restart server
+
+### Issue: Missing Required Dependencies
+
+**Symptom:**
+```
+Error: [oauth_single_audience] TOKEN_ENCRYPTION_KEY is required when ENABLE_SEMANTIC_SEARCH is enabled
+```
+
+**Solution:**
+When semantic search is enabled in multi-user modes, you need:
+- `TOKEN_ENCRYPTION_KEY` - Generate with: `python -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"`
+- `TOKEN_STORAGE_DB` - Path to SQLite database (e.g., `/app/data/tokens.db`)
+- `NEXTCLOUD_OIDC_CLIENT_ID` and `NEXTCLOUD_OIDC_CLIENT_SECRET` - For app password retrieval
+
+### Issue: Unexpected Mode Detected
+
+**Symptom:**
+Server activates `oauth_single_audience` mode when you expected `multi_user_basic`
+
+**Solution:**
+Add explicit mode declaration:
+```bash
+MCP_DEPLOYMENT_MODE=multi_user_basic
+ENABLE_MULTI_USER_BASIC_AUTH=true
+```
+
+---
+
+## Testing Your Migration
+
+### Step 1: Verify Configuration
+
+```bash
+# Set new variable names in .env
+cat .env | grep -E "(ENABLE_SEMANTIC_SEARCH|ENABLE_BACKGROUND_OPERATIONS|MCP_DEPLOYMENT_MODE)"
+```
+
+### Step 2: Check for Old Variable Names
+
+```bash
+# Should return nothing after migration
+cat .env | grep -E "(VECTOR_SYNC_ENABLED|ENABLE_OFFLINE_ACCESS)"
+```
+
+### Step 3: Start Server and Check Logs
+
+```bash
+# Start server
+docker-compose up mcp
+
+# Look for:
+# 1. No deprecation warnings
+# 2. Correct mode detected
+# 3. Auto-enablement messages (if using semantic search in multi-user mode)
+```
+
+**Expected Log Output (Multi-User OAuth + Semantic Search):**
+```
+INFO: Using explicit deployment mode: oauth_single_audience
+INFO: Automatically enabled background operations for semantic search in multi-user mode.
+INFO: Vector sync enabled. Starting background scanner...
+```
+
+### Step 4: Verify Functionality
+
+Test that existing features still work:
+- [ ] Semantic search returns results
+- [ ] Background indexing runs
+- [ ] OAuth flow completes successfully
+- [ ] Refresh tokens are stored/retrieved
+
+---
+
+## Quick Start Templates
+
+We provide mode-specific templates for new deployments:
+
+| Template | Use Case |
+|----------|----------|
+| `env.sample.single-user` | Simplest setup |
+| `env.sample.oauth-multi-user` | Recommended multi-user |
+| `env.sample.oauth-advanced` | Token exchange mode |
+
+**Usage:**
+```bash
+cp env.sample.oauth-multi-user .env
+# Edit .env with your values
+docker-compose up -d
+```
+
+---
+
+## Timeline and Support
+
+| Version | Status | Old Variable Support |
+|---------|--------|---------------------|
+| v0.57.x | Stable | Old names only |
+| v0.58.0 | Current | Both old and new (with warnings) |
+| v1.0.0 | Breaking | New names only |
+
+**Recommendation:** Migrate before v1.0.0 (12+ months minimum)
+
+---
+
+## Getting Help
+
+If you encounter issues during migration:
+
+1. **Check the logs** - Look for deprecation warnings and error messages
+2. **Review ADR-021** - See [docs/ADR-021-configuration-consolidation.md](ADR-021-configuration-consolidation.md)
+3. **Use mode-specific templates** - See `env.sample.*` files
+4. **File an issue** - Include your `.env` (redacted), logs, and mode
+
+---
+
+## Summary
+
+**What You Need to Do:**
+1. ✅ Rename `VECTOR_SYNC_ENABLED` → `ENABLE_SEMANTIC_SEARCH`
+2. ✅ (Optional) Rename `ENABLE_OFFLINE_ACCESS` → `ENABLE_BACKGROUND_OPERATIONS`
+3. ✅ (Recommended) Add `MCP_DEPLOYMENT_MODE` for clarity
+4. ✅ Remove redundant settings (semantic search auto-enables background ops in multi-user modes)
+5. ✅ Test your configuration
+
+**What the Server Does Automatically:**
+- ✅ Supports both old and new variable names
+- ✅ Logs deprecation warnings for old names
+- ✅ Auto-enables background operations when semantic search is enabled in multi-user modes
+- ✅ Validates configuration and provides clear error messages
+
+**Migration Timeline:**
+- Now → v1.0.0: Both old and new names work
+- v1.0.0+: Only new names supported
+
+**Questions?** See [docs/configuration.md](configuration.md) or file an issue.

docs/configuration.md

@@ -2,25 +2,82 @@
 
 The Nextcloud MCP server requires configuration to connect to your Nextcloud instance. Configuration is provided through environment variables, typically stored in a `.env` file.
 
+> **Note:** Configuration was significantly simplified in v0.58.0. If you're upgrading from v0.57.x, see the [Configuration Migration Guide](configuration-migration-v2.md).
+
 ## Quick Start
 
-Create a `.env` file based on `env.sample`:
+We provide mode-specific configuration templates for quick setup:
 
 ```bash
+# Choose a template based on your deployment mode:
+cp env.sample.single-user .env         # Simplest - one user, local dev
+cp env.sample.oauth-multi-user .env    # Recommended - multi-user OAuth
+cp env.sample.oauth-advanced .env      # Advanced - token exchange mode
+
+# Or start from the full example:
 cp env.sample .env
+
 # Edit .env with your Nextcloud details
 ```
 
-Then choose your authentication mode:
+Then choose your deployment mode:
 
-- [OAuth2/OIDC Configuration](#oauth2oidc-configuration) (Recommended)
+- [Single-User BasicAuth](#single-user-basicauth-mode) - Simplest for personal instances
-- [Basic Authentication Configuration](#basic-authentication-legacy)
+- [Multi-User OAuth](#multi-user-oauth-modes) - Recommended for production
+- [Deployment Mode Selection](#deployment-mode-selection) - Explicit mode declaration
 
 ---
 
-## OAuth2/OIDC Configuration
+## Deployment Mode Selection
 
-OAuth2/OIDC is the recommended authentication mode for production deployments.
+**New in v0.58.0:** You can explicitly declare your deployment mode to remove ambiguity and catch configuration errors early.
+
+```dotenv
+# Optional but recommended
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+```
+
+**Valid values:**
+- `single_user_basic` - Single-user with username/password
+- `multi_user_basic` - Multi-user with BasicAuth pass-through
+- `oauth_single_audience` - Multi-user OAuth (recommended)
+- `oauth_token_exchange` - Multi-user OAuth with token exchange
+- `smithery` - Smithery platform deployment
+
+**Benefits:**
+- ✅ Clear which mode is active
+- ✅ Better validation error messages
+- ✅ Self-documenting configuration
+- ✅ Catches configuration mistakes early
+
+**Auto-detection:** If `MCP_DEPLOYMENT_MODE` is not set, the server auto-detects the mode based on other settings (existing behavior).
+
+See [Authentication Modes](authentication.md) for detailed comparison of deployment modes.
+
+---
+
+## Single-User BasicAuth Mode
+
+BasicAuth with a single user is the simplest deployment mode. Use for personal instances, local development, and testing.
+
+```dotenv
+# Minimal single-user configuration
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+
+# Optional: Explicit mode declaration
+MCP_DEPLOYMENT_MODE=single_user_basic
+```
+
+> [!WARNING]
+> **Security Notice:** BasicAuth stores credentials in environment variables and is less secure than OAuth. Use OAuth for production multi-user deployments.
+
+---
+
+## Multi-User OAuth Modes
+
+OAuth2/OIDC is the recommended authentication mode for production multi-user deployments.
 
 ### Minimal Configuration (Auto-registration)
 
@@ -28,6 +85,9 @@ OAuth2/OIDC is the recommended authentication mode for production deployments.
 # .env file for OAuth with auto-registration
 NEXTCLOUD_HOST=https://your.nextcloud.instance.com
 
+# Optional: Explicit mode declaration (recommended)
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
 # Leave these EMPTY for OAuth mode
 NEXTCLOUD_USERNAME=
 NEXTCLOUD_PASSWORD=
@@ -41,6 +101,9 @@ This minimal configuration uses dynamic client registration to automatically reg
 # .env file for OAuth with pre-configured client
 NEXTCLOUD_HOST=https://your.nextcloud.instance.com
 
+# Optional: Explicit mode declaration (recommended)
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
 # OAuth Client Credentials (optional - auto-registers if not provided)
 NEXTCLOUD_OIDC_CLIENT_ID=your-client-id
 NEXTCLOUD_OIDC_CLIENT_SECRET=your-client-secret
@@ -110,8 +173,50 @@ NEXTCLOUD_PASSWORD=your_app_password_or_password
 
 ## Semantic Search Configuration (Optional)
 
+**New in v0.58.0:** Simplified semantic search configuration with automatic dependency resolution.
+
 The MCP server includes semantic search capabilities powered by vector embeddings. This feature requires a vector database (Qdrant) and an embedding service.
 
+### Quick Start
+
+**Single-User Mode:**
+```dotenv
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+
+# Enable semantic search
+ENABLE_SEMANTIC_SEARCH=true
+
+# Vector database
+QDRANT_LOCATION=:memory:
+
+# Embedding provider
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+**Multi-User OAuth Mode:**
+```dotenv
+NEXTCLOUD_HOST=https://nextcloud.example.com
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# Enable semantic search
+# In multi-user modes, this AUTOMATICALLY enables background operations!
+ENABLE_SEMANTIC_SEARCH=true
+
+# Required for background operations (auto-enabled by semantic search)
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+
+# Vector database
+QDRANT_URL=http://qdrant:6333
+
+# Embedding provider
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+> **Note:** In multi-user modes (OAuth, Multi-User BasicAuth), enabling `ENABLE_SEMANTIC_SEARCH` automatically enables background operations and refresh token storage. You don't need to set `ENABLE_BACKGROUND_OPERATIONS` separately!
+
 ### Qdrant Vector Database Modes
 
 The server supports three Qdrant deployment modes:
@@ -126,7 +231,7 @@ No configuration needed! If neither `QDRANT_URL` nor `QDRANT_LOCATION` is set, t
 
 ```dotenv
 # No Qdrant configuration needed - defaults to :memory:
-VECTOR_SYNC_ENABLED=true
+ENABLE_SEMANTIC_SEARCH=true
 ```
 
 **Pros:**
@@ -145,7 +250,7 @@ For single-instance deployments that need persistence without a separate Qdrant
 ```dotenv
 # Local persistent storage
 QDRANT_LOCATION=/app/data/qdrant  # Or any writable path
-VECTOR_SYNC_ENABLED=true
+ENABLE_SEMANTIC_SEARCH=true
 ```
 
 **Pros:**
@@ -166,7 +271,7 @@ For production deployments with a dedicated Qdrant service:
 QDRANT_URL=http://qdrant:6333
 QDRANT_API_KEY=your-secret-api-key  # Optional
 QDRANT_COLLECTION=nextcloud_content  # Optional
-VECTOR_SYNC_ENABLED=true
+ENABLE_SEMANTIC_SEARCH=true
 ```
 
 **Pros:**
@@ -283,13 +388,15 @@ Solutions:
 - Data corruption in Qdrant
 - Confusing error messages during indexing
 
-### Vector Sync Configuration
+### Background Indexing Configuration
 
 Control background indexing behavior:
 
 ```dotenv
-# Vector sync settings (ADR-007)
+# Semantic search (ADR-007, ADR-021)
-VECTOR_SYNC_ENABLED=true              # Enable background indexing
+ENABLE_SEMANTIC_SEARCH=true           # Enable background indexing
+
+# Tuning parameters (advanced - only modify if needed)
 VECTOR_SYNC_SCAN_INTERVAL=300         # Scan interval in seconds (default: 5 minutes)
 VECTOR_SYNC_PROCESSOR_WORKERS=3       # Concurrent indexing workers (default: 3)
 VECTOR_SYNC_QUEUE_MAX_SIZE=10000      # Max queued documents (default: 10000)
@@ -299,6 +406,8 @@ DOCUMENT_CHUNK_SIZE=512               # Words per chunk (default: 512)
 DOCUMENT_CHUNK_OVERLAP=50             # Overlapping words between chunks (default: 50)
 ```
 
+> **Note:** The `VECTOR_SYNC_*` tuning parameters keep their names as they're implementation details. Only the user-facing feature flag was renamed to `ENABLE_SEMANTIC_SEARCH`.
+
 ### Embedding Service Configuration
 
 The server uses an embedding service to generate vector representations. Two options are available:
@@ -369,11 +478,11 @@ DOCUMENT_CHUNK_OVERLAP=100
 
 | Variable | Required | Default | Description |
 |----------|----------|---------|-------------|
+| `ENABLE_SEMANTIC_SEARCH` | ⚠️ Optional | `false` | Enable semantic search with background indexing (replaces `VECTOR_SYNC_ENABLED`) |
 | `QDRANT_URL` | ⚠️ Optional | - | Qdrant service URL (network mode) - mutually exclusive with `QDRANT_LOCATION` |
 | `QDRANT_LOCATION` | ⚠️ Optional | `:memory:` | Local Qdrant path (`:memory:` or `/path/to/data`) - mutually exclusive with `QDRANT_URL` |
 | `QDRANT_API_KEY` | ⚠️ Optional | - | Qdrant API key (network mode only) |
-| `QDRANT_COLLECTION` | ⚠️ Optional | `nextcloud_content` | Qdrant collection name |
+| `QDRANT_COLLECTION` | ⚠️ Optional | Auto-generated | Qdrant collection name |
-| `VECTOR_SYNC_ENABLED` | ⚠️ Optional | `false` | Enable background vector indexing |
 | `VECTOR_SYNC_SCAN_INTERVAL` | ⚠️ Optional | `300` | Document scan interval (seconds) |
 | `VECTOR_SYNC_PROCESSOR_WORKERS` | ⚠️ Optional | `3` | Concurrent indexing workers |
 | `VECTOR_SYNC_QUEUE_MAX_SIZE` | ⚠️ Optional | `10000` | Max queued documents |
@@ -383,6 +492,9 @@ DOCUMENT_CHUNK_OVERLAP=100
 | `DOCUMENT_CHUNK_SIZE` | ⚠️ Optional | `512` | Words per chunk for document embedding |
 | `DOCUMENT_CHUNK_OVERLAP` | ⚠️ Optional | `50` | Overlapping words between chunks (must be < chunk size) |
 
+**Deprecated variables (still functional):**
+- `VECTOR_SYNC_ENABLED` - Use `ENABLE_SEMANTIC_SEARCH` instead (will be removed in v1.0.0)
+
 ### Docker Compose Example
 
 Enable network mode Qdrant with docker-compose:
@@ -392,7 +504,7 @@ services:
   mcp:
     environment:
       - QDRANT_URL=http://qdrant:6333
-      - VECTOR_SYNC_ENABLED=true
+      - ENABLE_SEMANTIC_SEARCH=true
 
   qdrant:
     image: qdrant/qdrant:latest
@@ -545,6 +657,7 @@ uv run nextcloud-mcp-server --no-oauth \
 
 ## See Also
 
+- [Configuration Migration Guide v2](configuration-migration-v2.md) - **New in v0.58.0:** Migrate from old variable names
 - [OAuth Quick Start](quickstart-oauth.md) - 5-minute OAuth setup for development
 - [OAuth Setup Guide](oauth-setup.md) - Detailed OAuth configuration for production
 - [OAuth Architecture](oauth-architecture.md) - How OAuth works in the MCP server
@@ -553,3 +666,4 @@ uv run nextcloud-mcp-server --no-oauth \
 - [Running the Server](running.md) - Starting the server with different configurations
 - [Troubleshooting](troubleshooting.md) - Common configuration issues
 - [OAuth Troubleshooting](oauth-troubleshooting.md) - OAuth-specific troubleshooting
+- [ADR-021](ADR-021-configuration-consolidation.md) - Configuration consolidation architecture decision

docs/database-migrations.md

@@ -0,0 +1,301 @@
+# Database Migrations
+
+This document describes the database migration system for nextcloud-mcp-server's token storage database.
+
+## Overview
+
+The token storage database uses [Alembic](https://alembic.sqlalchemy.org/) for schema versioning and migrations. Alembic provides:
+
+- **Version Control**: Track schema changes in Git
+- **Rollback Support**: Safely downgrade schema if needed
+- **Audit Trail**: Migration files serve as schema changelog
+- **Automated Upgrades**: Database schema updates automatically on startup
+
+## Architecture
+
+### Migration Strategy
+
+The system handles three scenarios:
+
+1. **New Database**: Runs migrations from scratch to create all tables
+2. **Pre-Alembic Database**: Stamps existing database with initial revision (no changes)
+3. **Alembic-Managed Database**: Upgrades to latest version automatically
+
+### Directory Structure
+
+```
+nextcloud-mcp-server/
+├── alembic/                              # Alembic migrations
+│   ├── versions/                         # Migration scripts
+│   │   └── 20251217_2200_001_initial_schema.py
+│   ├── env.py                            # Alembic environment
+│   ├── script.py.mako                    # Migration template
+│   └── README                            # Migration usage guide
+├── alembic.ini                           # Alembic configuration
+└── nextcloud_mcp_server/
+    ├── auth/storage.py                   # Uses migrations on init
+    └── migrations.py                     # Migration utilities
+```
+
+## Usage
+
+### Automatic Migration on Startup
+
+Migrations run automatically when the server starts:
+
+```bash
+uv run nextcloud-mcp-server
+```
+
+The `RefreshTokenStorage.initialize()` method:
+1. Checks if database is Alembic-managed
+2. Stamps pre-Alembic databases with initial revision
+3. Upgrades to latest version
+
+### Manual Migration Commands
+
+```bash
+# Show current database version
+uv run nextcloud-mcp-server db current
+
+# Upgrade database to latest version
+uv run nextcloud-mcp-server db upgrade
+
+# Show migration history
+uv run nextcloud-mcp-server db history
+
+# Downgrade by one version (emergency use only)
+uv run nextcloud-mcp-server db downgrade
+
+# Specify custom database path
+uv run nextcloud-mcp-server db current -d /path/to/tokens.db
+```
+
+### Environment Variables
+
+- `TOKEN_STORAGE_DB`: Path to database file (default: `/app/data/tokens.db`)
+
+## Creating Migrations (Developers)
+
+### Step 1: Create Migration File
+
+```bash
+uv run nextcloud-mcp-server db migrate "add user preferences table"
+```
+
+This creates a new migration file in `alembic/versions/` with empty `upgrade()` and `downgrade()` functions.
+
+### Step 2: Write Migration SQL
+
+Since we don't use SQLAlchemy models, write raw SQL:
+
+```python
+def upgrade() -> None:
+    """Add user preferences table."""
+    op.execute("""
+        CREATE TABLE user_preferences (
+            user_id TEXT PRIMARY KEY,
+            theme TEXT DEFAULT 'light',
+            language TEXT DEFAULT 'en',
+            created_at INTEGER NOT NULL
+        )
+    """)
+
+    op.execute("""
+        CREATE INDEX idx_user_preferences_user_id
+        ON user_preferences(user_id)
+    """)
+
+
+def downgrade() -> None:
+    """Remove user preferences table."""
+    op.execute("DROP INDEX IF EXISTS idx_user_preferences_user_id")
+    op.execute("DROP TABLE IF EXISTS user_preferences")
+```
+
+### Step 3: Test Migration
+
+```bash
+# Test upgrade
+uv run nextcloud-mcp-server db upgrade -d /tmp/test.db
+
+# Verify schema
+sqlite3 /tmp/test.db ".schema"
+
+# Test downgrade
+uv run nextcloud-mcp-server db downgrade -d /tmp/test.db
+
+# Verify removal
+sqlite3 /tmp/test.db ".schema"
+```
+
+### Step 4: Commit Migration
+
+```bash
+git add alembic/versions/YYYYMMDD_HHMM_XXX_description.py
+git commit -m "feat: add user preferences table migration"
+```
+
+## SQLite Limitations
+
+SQLite has limited `ALTER TABLE` support:
+
+### Supported Operations
+
+- ✅ Add columns: `ALTER TABLE table ADD COLUMN ...`
+- ✅ Rename table: `ALTER TABLE old RENAME TO new`
+- ✅ Rename column: `ALTER TABLE table RENAME COLUMN old TO new` (SQLite 3.25+)
+
+### Unsupported Operations (Requires Table Recreation)
+
+- ❌ Drop column
+- ❌ Change column type
+- ❌ Add constraints to existing columns
+
+### Table Recreation Pattern
+
+For complex schema changes:
+
+```python
+def upgrade() -> None:
+    # Create new table with desired schema
+    op.execute("""
+        CREATE TABLE refresh_tokens_new (
+            user_id TEXT PRIMARY KEY,
+            encrypted_token BLOB NOT NULL,
+            new_field TEXT,  -- New column
+            expires_at INTEGER,
+            created_at INTEGER NOT NULL
+        )
+    """)
+
+    # Copy data from old table
+    op.execute("""
+        INSERT INTO refresh_tokens_new
+        (user_id, encrypted_token, expires_at, created_at)
+        SELECT user_id, encrypted_token, expires_at, created_at
+        FROM refresh_tokens
+    """)
+
+    # Drop old table and rename new table
+    op.execute("DROP TABLE refresh_tokens")
+    op.execute("ALTER TABLE refresh_tokens_new RENAME TO refresh_tokens")
+
+    # Recreate indexes
+    op.execute("CREATE INDEX idx_user_id ON refresh_tokens(user_id)")
+```
+
+## Best Practices
+
+### Naming Conventions
+
+- **Migrations**: `YYYYMMDD_HHMM_XXX_description.py`
+- **Revision IDs**: Sequential numbers (`001`, `002`, `003`)
+- **Descriptions**: Imperative mood ("add table", "remove column")
+
+### Migration Guidelines
+
+1. **Test Thoroughly**: Test both upgrade and downgrade paths
+2. **Preserve Data**: Ensure data migration logic is correct
+3. **Document Changes**: Add comments explaining complex operations
+4. **Small Changes**: One logical change per migration
+5. **No Breaking Changes**: Maintain backward compatibility when possible
+
+### Downgrade Considerations
+
+- **Data Loss**: Downgrade may lose data (dropped columns, tables)
+- **Confirmation**: Downgrade command requires explicit confirmation
+- **Testing**: Always test downgrade path before deploying
+- **Emergency Only**: Use downgrades only for critical rollbacks
+
+## Backward Compatibility
+
+### Pre-Alembic Databases
+
+Existing databases created before Alembic integration are automatically detected and stamped with revision `001`:
+
+1. Server detects no `alembic_version` table
+2. Checks if `refresh_tokens` table exists
+3. If yes, stamps database with `001` (no schema changes)
+4. Future updates use normal migration path
+
+### Migration Path
+
+```
+Pre-Alembic DB → Stamp(001) → Upgrade(002) → Upgrade(003) → ...
+New DB → Migrate(001) → Upgrade(002) → Upgrade(003) → ...
+```
+
+## Troubleshooting
+
+### Migration Fails
+
+```bash
+# Check current state
+uv run nextcloud-mcp-server db current -d /path/to/tokens.db
+
+# View migration history
+uv run nextcloud-mcp-server db history -d /path/to/tokens.db
+
+# Manually inspect database
+sqlite3 /path/to/tokens.db ".schema"
+```
+
+### Reset to Initial State
+
+**WARNING: This destroys all data!**
+
+```bash
+# Downgrade to base (empty database)
+uv run nextcloud-mcp-server db downgrade -d /path/to/tokens.db --revision base
+
+# Upgrade to latest
+uv run nextcloud-mcp-server db upgrade -d /path/to/tokens.db
+```
+
+### Corrupted Migration State
+
+If `alembic_version` table is corrupted:
+
+```bash
+# Manually fix via SQL
+sqlite3 /path/to/tokens.db
+> DELETE FROM alembic_version;
+> INSERT INTO alembic_version (version_num) VALUES ('001');
+> .quit
+
+# Verify and upgrade
+uv run nextcloud-mcp-server db current -d /path/to/tokens.db
+uv run nextcloud-mcp-server db upgrade -d /path/to/tokens.db
+```
+
+## CI/CD Integration
+
+### Pre-Deployment
+
+```bash
+# Run migrations in test environment
+export TOKEN_STORAGE_DB=/app/data/tokens.db
+uv run nextcloud-mcp-server db upgrade
+
+# Verify current version
+uv run nextcloud-mcp-server db current
+```
+
+### Docker Deployment
+
+Migrations run automatically on container startup via `RefreshTokenStorage.initialize()`.
+
+### Rollback Plan
+
+1. Stop application
+2. Backup database: `cp tokens.db tokens.db.backup`
+3. Downgrade: `uv run nextcloud-mcp-server db downgrade --revision XXX`
+4. Deploy previous application version
+5. Restart application
+
+## References
+
+- [Alembic Documentation](https://alembic.sqlalchemy.org/)
+- [SQLite ALTER TABLE Limitations](https://www.sqlite.org/lang_altertable.html)
+- [ADR-004: Progressive Consent](./ADR-004-progressive-consent.md) (migration 001)

docs/running.md

@@ -14,100 +14,10 @@ Before running the server:
 
 ## Quick Start
 
-Load your environment variables and start the server:
+Start the server using Docker:
 
 ```bash
-# Load environment variables from .env
+# OAuth mode (recommended)
-export $(grep -v '^#' .env | xargs)
-
-# Start the server
-uv run nextcloud-mcp-server
-```
-
-The server will start on `http://127.0.0.1:8000` by default.
-
----
-
-## Running Locally
-
-### Method 1: Using nextcloud-mcp-server CLI (Recommended)
-
-The CLI provides a simple interface with built-in defaults:
-
-#### OAuth Mode
-
-```bash
-# Auto-detected when NEXTCLOUD_USERNAME/PASSWORD not set
-uv run nextcloud-mcp-server
-
-# Explicitly force OAuth mode
-uv run nextcloud-mcp-server --oauth
-
-# OAuth with custom host and port
-uv run nextcloud-mcp-server --oauth --host 0.0.0.0 --port 8080
-
-# OAuth with pre-configured client
-uv run nextcloud-mcp-server --oauth \
-  --oauth-client-id abc123 \
-  --oauth-client-secret xyz789
-
-# OAuth with specific apps only
-uv run nextcloud-mcp-server --oauth \
-  --enable-app notes \
-  --enable-app calendar
-```
-
-#### BasicAuth Mode (Legacy)
-
-```bash
-# Auto-detected when NEXTCLOUD_USERNAME/PASSWORD are set
-uv run nextcloud-mcp-server
-
-# Explicitly force BasicAuth mode
-uv run nextcloud-mcp-server --no-oauth
-
-# BasicAuth with specific apps
-uv run nextcloud-mcp-server --no-oauth \
-  --enable-app notes \
-  --enable-app webdav
-```
-
-### Method 2: Using uvicorn
-
-For more control over server options (workers, reload, etc.):
-
-```bash
-# Load environment variables
-export $(grep -v '^#' .env | xargs)
-
-# Run with uvicorn
-uv run uvicorn nextcloud_mcp_server.app:get_app \
-  --factory \
-  --host 127.0.0.1 \
-  --port 8000 \
-  --reload  # Enable auto-reload for development
-```
-
-See all uvicorn options at [https://www.uvicorn.org/settings/](https://www.uvicorn.org/settings/)
-
-### Method 3: Using Python Module
-
-```bash
-# Load environment variables
-export $(grep -v '^#' .env | xargs)
-
-# Run as Python module
-python -m nextcloud_mcp_server.app --oauth --port 8000
-```
-
----
-
-## Running with Docker
-
-### Basic Docker Run
-
-```bash
-# OAuth mode
 docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
   ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
 
@@ -116,11 +26,56 @@ docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
   ghcr.io/cbcoutinho/nextcloud-mcp-server:latest
 ```
 
-### Docker with Persistent OAuth Storage
+The server will start on `http://127.0.0.1:8000` by default.
+
+---
+
+## Running with Docker
+
+### Basic Docker Run
+
+#### OAuth Mode (Recommended)
 
 ```bash
+# OAuth with auto-registration
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
+
+# OAuth with custom port
+docker run -p 127.0.0.1:8080:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
+
+# OAuth with pre-configured client
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  -e NEXTCLOUD_OIDC_CLIENT_ID=abc123 \
+  -e NEXTCLOUD_OIDC_CLIENT_SECRET=xyz789 \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
+
+# OAuth with specific apps only
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --enable-app notes --enable-app calendar
+```
+
+#### BasicAuth Mode (Legacy)
+
+```bash
+# BasicAuth (requires NEXTCLOUD_USERNAME/PASSWORD in .env)
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest
+
+# BasicAuth with specific apps
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest \
+  --enable-app notes --enable-app webdav
+```
+
+### Docker with Persistent Token Storage
+
+```bash
+# Mount volume for persistent OAuth token storage
 docker run -p 127.0.0.1:8000:8000 --env-file .env \
-  -v $(pwd)/.oauth:/app/.oauth \
+  -v $(pwd)/data:/app/data \
   --rm ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
 ```
 
@@ -140,7 +95,7 @@ services:
     env_file:
       - .env
     volumes:
-      - ./oauth-storage:/app/.oauth
+      - ./data:/app/data  # Persistent token storage
     restart: unless-stopped
 ```
 
@@ -168,30 +123,39 @@ docker-compose down
 
 ```bash
 # Bind to all interfaces (accessible from network)
-uv run nextcloud-mcp-server --host 0.0.0.0 --port 8000
+docker run -p 0.0.0.0:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
 
 # Bind to localhost only (default, more secure)
-uv run nextcloud-mcp-server --host 127.0.0.1 --port 8000
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
 
-# Use a different port
+# Use a different port (map host port 8080 to container port 8000)
-uv run nextcloud-mcp-server --port 8080
+docker run -p 127.0.0.1:8080:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
 ```
 
-**Security Note:** Using `--host 0.0.0.0` exposes the server to your network. Only use this if you understand the security implications.
+**Security Note:** Binding to `0.0.0.0` exposes the server to your network. Only use this if you understand the security implications.
 
 ### Transport Protocols
 
 The server supports multiple MCP transport protocols:
 
 ```bash
-# Streamable HTTP (recommended)
+# Streamable HTTP (default, recommended)
-uv run nextcloud-mcp-server --transport streamable-http
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --transport streamable-http
 
-# SSE - Server-Sent Events (default, deprecated)
+# SSE - Server-Sent Events (deprecated)
-uv run nextcloud-mcp-server --transport sse
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --transport sse
 
 # HTTP
-uv run nextcloud-mcp-server --transport http
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --transport http
 ```
 
 > [!WARNING]
@@ -201,10 +165,14 @@ uv run nextcloud-mcp-server --transport http
 
 ```bash
 # Set log level (critical, error, warning, info, debug, trace)
-uv run nextcloud-mcp-server --log-level debug
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --log-level debug
 
 # Production: use warning or error
-uv run nextcloud-mcp-server --log-level warning
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --log-level warning
 ```
 
 ### Selective App Enablement
@@ -212,22 +180,26 @@ uv run nextcloud-mcp-server --log-level warning
 By default, all supported Nextcloud apps are enabled. You can enable specific apps only:
 
 ```bash
-# Available apps: notes, tables, webdav, calendar, contacts, deck
+# Available apps: notes, tables, webdav, calendar, contacts, cookbook, deck
 
 # Enable all apps (default)
-uv run nextcloud-mcp-server
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth
 
 # Enable only Notes
-uv run nextcloud-mcp-server --enable-app notes
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --enable-app notes
 
 # Enable multiple apps
-uv run nextcloud-mcp-server \
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
-  --enable-app notes \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
-  --enable-app calendar \
+  --enable-app notes --enable-app calendar --enable-app contacts
-  --enable-app contacts
 
 # Enable only WebDAV for file operations
-uv run nextcloud-mcp-server --enable-app webdav
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --enable-app webdav
 ```
 
 **Use cases:**
@@ -240,24 +212,68 @@ uv run nextcloud-mcp-server --enable-app webdav
 
 ## Development Mode
 
-For active development with auto-reload:
+### Running for Development
+
+For active development with auto-reload, mount your source code as a volume:
 
 ```bash
-# Using uvicorn with reload
+# Development mode with source code mounted
-uv run uvicorn nextcloud_mcp_server.app:get_app \
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
-  --factory \
+  -v $(pwd):/app \
-  --reload \
+  -v $(pwd)/data:/app/data \
-  --host 127.0.0.1 \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
-  --port 8000 \
   --log-level debug
 ```
 
-Or use the CLI with reload flag:
+For local development without Docker:
 
 ```bash
-uv run nextcloud-mcp-server --reload --log-level debug
+# Load environment variables
+export $(grep -v '^#' .env | xargs)
+
+# Run the server with auto-reload
+uv run nextcloud-mcp-server run --oauth --log-level debug
 ```
 
+### CLI Subcommands
+
+The `nextcloud-mcp-server` CLI has two main subcommands:
+
+1. **`run`** - Start the MCP server (default command in Docker)
+   ```bash
+   uv run nextcloud-mcp-server run --oauth --host 0.0.0.0 --port 8000
+   ```
+
+2. **`db`** - Database migration management (Alembic)
+   ```bash
+   # Show current migration revision
+   uv run nextcloud-mcp-server db current
+
+   # Upgrade to latest migration
+   uv run nextcloud-mcp-server db upgrade
+
+   # Show migration history
+   uv run nextcloud-mcp-server db history
+
+   # Create new migration (developers only)
+   uv run nextcloud-mcp-server db migrate "description of changes"
+   ```
+
+### Database Migrations
+
+Token storage uses **Alembic** for schema management:
+
+- **Automatic migrations**: Database is upgraded automatically on server startup
+- **Backward compatibility**: Pre-Alembic databases are automatically stamped with the initial revision
+- **Migration files**: Located in `alembic/versions/`
+- **For developers**: When changing the schema:
+  1. Create a migration: `uv run nextcloud-mcp-server db migrate "add new column"`
+  2. Edit the generated file in `alembic/versions/` to add SQL statements
+  3. Test upgrade: `uv run nextcloud-mcp-server db upgrade`
+  4. Test downgrade: `uv run nextcloud-mcp-server db downgrade`
+
+See [Database Migrations Guide](database-migrations.md) for detailed information.
+
 ---
 
 ## Connecting to the Server
@@ -266,15 +282,15 @@ uv run nextcloud-mcp-server --reload --log-level debug
 
 MCP Inspector is a browser-based tool for testing MCP servers:
 
-```bash
+1. Start your MCP server using Docker (see above)
-# Start MCP Inspector
+2. Start MCP Inspector:
-uv run mcp dev
+   ```bash
-
+   npx @modelcontextprotocol/inspector
-# In the browser:
+   ```
-# 1. Enter server URL: http://localhost:8000
+3. In the browser:
-# 2. Complete OAuth flow (if using OAuth)
+   - Enter server URL: `http://localhost:8000`
-# 3. Explore tools and resources
+   - Complete OAuth flow (if using OAuth)
-```
+   - Explore tools and resources
 
 ### Using MCP Clients
 
@@ -322,48 +338,13 @@ INFO     Initializing Nextcloud client with BasicAuth
 
 ### Running as a Background Service
 
-#### Using systemd (Linux)
+Use Docker Compose with `restart: unless-stopped` (see [Docker Compose section](#docker-compose) above).
-
-Create `/etc/systemd/system/nextcloud-mcp.service`:
-
-```ini
-[Unit]
-Description=Nextcloud MCP Server
-After=network.target
-
-[Service]
-Type=simple
-User=your-user
-WorkingDirectory=/path/to/nextcloud-mcp-server
-EnvironmentFile=/path/to/.env
-ExecStart=/path/to/uv run nextcloud-mcp-server --oauth
-Restart=on-failure
-RestartSec=10
-
-[Install]
-WantedBy=multi-user.target
-```
-
-Enable and start:
-
-```bash
-sudo systemctl daemon-reload
-sudo systemctl enable nextcloud-mcp
-sudo systemctl start nextcloud-mcp
-sudo systemctl status nextcloud-mcp
-```
-
-#### Using Docker Compose
-
-See [Docker Compose section](#docker-compose) above - includes `restart: unless-stopped`.
 
 ### Monitoring Logs
 
 ```bash
-# Local installation with systemd
+# Docker (find container name first)
-sudo journalctl -u nextcloud-mcp -f
+docker ps
-
-# Docker
 docker logs -f <container-name>
 
 # Docker Compose
@@ -374,35 +355,38 @@ docker-compose logs -f mcp
 
 ## Performance Tuning
 
-### Multiple Workers
-
-For production deployments with higher load:
-
-```bash
-# Using CLI (if supported)
-uv run nextcloud-mcp-server --workers 4
-
-# Using uvicorn
-uv run uvicorn nextcloud_mcp_server.app:get_app \
-  --factory \
-  --workers 4 \
-  --host 0.0.0.0 \
-  --port 8000
-```
-
 ### Production Settings
 
-```bash
+For production deployments, use Docker Compose with the recommended settings:
-# Recommended production configuration
+
-uv run nextcloud-mcp-server \
+```yaml
-  --oauth \
+version: '3.8'
-  --host 127.0.0.1 \
+
-  --port 8000 \
+services:
-  --log-level warning \
+  mcp:
-  --transport streamable-http \
+    image: ghcr.io/cbcoutinho/nextcloud-mcp-server:latest
-  --workers 2
+    command: --oauth --log-level warning --transport streamable-http
+    ports:
+      - "127.0.0.1:8000:8000"
+    env_file:
+      - .env
+    volumes:
+      - ./data:/app/data
+    restart: unless-stopped
+    deploy:
+      resources:
+        limits:
+          cpus: '2'
+          memory: 1G
+        reservations:
+          cpus: '0.5'
+          memory: 512M
 ```
 
+### Scaling with Multiple Replicas
+
+For higher load, use Docker Swarm or Kubernetes. See the [Helm Chart](../helm/) for Kubernetes deployments.
+
 ---
 
 ## Troubleshooting
@@ -411,12 +395,18 @@ uv run nextcloud-mcp-server \
 
 Check logs for errors:
 ```bash
-uv run nextcloud-mcp-server --log-level debug
+# View container logs
+docker logs <container-name>
+
+# Or run with debug logging
+docker run -p 127.0.0.1:8000:8000 --env-file .env --rm \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest --oauth \
+  --log-level debug
 ```
 
 Common issues:
-- Environment variables not loaded - See [Configuration](configuration.md#loading-environment-variables)
+- Environment variables not loaded - Check your `.env` file
-- Port already in use - Try a different port with `--port`
+- Port already in use - Use a different host port (e.g., `-p 127.0.0.1:8080:8000`)
 - OAuth configuration errors - See [Troubleshooting](troubleshooting.md)
 
 ### Can't connect to server

docs/semantic-search-architecture.md

@@ -5,7 +5,7 @@ This document explains the architecture of the semantic search feature in the Ne
 > [!IMPORTANT]
 > **Status: Experimental**
 > - Disabled by default (`VECTOR_SYNC_ENABLED=false`)
-> - Currently supports **Notes app only** (multi-app architecture ready, additional apps planned)
+> - Currently supports **Notes, Files (PDFs), News items, and Deck cards**
 > - Requires additional infrastructure (Qdrant vector database + Ollama embedding service)
 > - RAG answer generation requires MCP client sampling support
 
@@ -39,9 +39,9 @@ Semantic search enables:
 
 ### Current Support
 
-- **Supported Apps**: Notes (fully implemented)
+- **Supported Apps**: Notes, Files (PDFs with text extraction), News items, Deck cards
-- **Planned Apps**: Calendar events, Calendar tasks, Deck cards, Files (with text extraction), Contacts
+- **Planned Apps**: Calendar events, Calendar tasks, Contacts
-- **Architecture**: Multi-app plugin system ready, awaiting implementation
+- **Architecture**: Multi-app plugin system ready for additional apps
 
 ## System Components
 

docs/troubleshooting.md

@@ -4,6 +4,146 @@ This guide covers common issues and solutions for the Nextcloud MCP server.
 
 > **OAuth-specific issues?** See the dedicated [OAuth Troubleshooting Guide](oauth-troubleshooting.md) for OAuth authentication problems, OIDC discovery issues, token validation failures, and more.
 
+> **Upgrading from v0.57.x?** See the [Configuration Migration Guide](configuration-migration-v2.md) for help with new variable names.
+
+## Configuration Issues (v0.58.0+)
+
+### Issue: Deprecation warning for VECTOR_SYNC_ENABLED
+
+**Symptom:**
+```
+WARNING: VECTOR_SYNC_ENABLED is deprecated. Please use ENABLE_SEMANTIC_SEARCH instead.
+```
+
+**Cause:** You're using the old variable name from v0.57.x.
+
+**Solution:**
+```bash
+# In your .env file, replace:
+VECTOR_SYNC_ENABLED=true
+
+# With:
+ENABLE_SEMANTIC_SEARCH=true
+```
+
+See [Configuration Migration Guide](configuration-migration-v2.md) for complete migration instructions.
+
+---
+
+### Issue: Deprecation warning for ENABLE_OFFLINE_ACCESS
+
+**Symptom:**
+```
+WARNING: ENABLE_OFFLINE_ACCESS is deprecated. Please use ENABLE_BACKGROUND_OPERATIONS instead.
+```
+
+**Cause:** You're using the old variable name from v0.57.x.
+
+**Solution:**
+
+**If you have semantic search enabled:**
+```bash
+# In multi-user modes, you can remove ENABLE_OFFLINE_ACCESS entirely!
+# ENABLE_SEMANTIC_SEARCH automatically enables background operations
+
+# Before (v0.57.x):
+ENABLE_OFFLINE_ACCESS=true
+VECTOR_SYNC_ENABLED=true
+
+# After (v0.58.0+):
+ENABLE_SEMANTIC_SEARCH=true  # This is all you need!
+```
+
+**If you only want background operations (no semantic search):**
+```bash
+# Replace:
+ENABLE_OFFLINE_ACCESS=true
+
+# With:
+ENABLE_BACKGROUND_OPERATIONS=true
+```
+
+---
+
+### Issue: "Invalid MCP_DEPLOYMENT_MODE"
+
+**Symptom:**
+```
+ValueError: Invalid MCP_DEPLOYMENT_MODE: 'oauth'. Valid values: single_user_basic, multi_user_basic, oauth_single_audience, oauth_token_exchange, smithery
+```
+
+**Cause:** Invalid value for `MCP_DEPLOYMENT_MODE`.
+
+**Solution:**
+Use one of the valid mode values:
+```bash
+# Correct values:
+MCP_DEPLOYMENT_MODE=single_user_basic          # Single-user with username/password
+MCP_DEPLOYMENT_MODE=multi_user_basic           # Multi-user BasicAuth
+MCP_DEPLOYMENT_MODE=oauth_single_audience      # OAuth (recommended)
+MCP_DEPLOYMENT_MODE=oauth_token_exchange       # OAuth with token exchange
+MCP_DEPLOYMENT_MODE=smithery                   # Smithery deployment
+```
+
+Or remove `MCP_DEPLOYMENT_MODE` to use automatic detection.
+
+---
+
+### Issue: Missing TOKEN_ENCRYPTION_KEY when semantic search enabled
+
+**Symptom:**
+```
+Error: [oauth_single_audience] TOKEN_ENCRYPTION_KEY is required when ENABLE_SEMANTIC_SEARCH is enabled
+```
+
+**Cause:** In multi-user modes, semantic search automatically enables background operations, which require encrypted token storage.
+
+**Solution:**
+Generate an encryption key and add required token storage configuration:
+
+```bash
+# Generate encryption key
+python -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"
+
+# Add to .env:
+TOKEN_ENCRYPTION_KEY=<generated-key>
+TOKEN_STORAGE_DB=/app/data/tokens.db
+NEXTCLOUD_OIDC_CLIENT_ID=your-client-id       # Required for app password retrieval
+NEXTCLOUD_OIDC_CLIENT_SECRET=your-client-secret
+```
+
+**Why this happens:**
+- v0.58.0+ automatically enables background operations when `ENABLE_SEMANTIC_SEARCH=true` in multi-user modes
+- Background operations need encrypted refresh token storage
+- This simplifies configuration but requires the encryption infrastructure
+
+See [Configuration Guide - Semantic Search](configuration.md#semantic-search-configuration-optional) for details.
+
+---
+
+### Issue: Both old and new variable names set
+
+**Symptom:**
+```
+WARNING: Both ENABLE_SEMANTIC_SEARCH and VECTOR_SYNC_ENABLED are set. Using ENABLE_SEMANTIC_SEARCH.
+```
+
+**Cause:** You have both the old and new variable names in your configuration.
+
+**Solution:**
+Remove the old variable name:
+```bash
+# Remove this line:
+VECTOR_SYNC_ENABLED=true
+
+# Keep this line:
+ENABLE_SEMANTIC_SEARCH=true
+```
+
+The server will use the new name and ignore the old one, but it's cleaner to remove the old variable entirely.
+
+---
+
 ## OAuth Issues (Quick Reference)
 
 ### Issue: "OAuth mode requires NEXTCLOUD_HOST environment variable"

env.sample

@@ -1,198 +1,236 @@
-# Nextcloud Instance
+# ============================================
+# DEPLOYMENT MODE SELECTION
+# ============================================
+# Optional: Explicitly declare deployment mode (ADR-021)
+# If not set, mode is auto-detected from other settings
+# Valid values: single_user_basic, multi_user_basic, oauth_single_audience,
+#               oauth_token_exchange, smithery
+#
+# Recommendation: Set this for clarity and to catch configuration errors early
+#MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# ============================================
+# COMMON SETTINGS (Required for all modes)
+# ============================================
+# Your Nextcloud instance URL (without trailing slash)
 NEXTCLOUD_HOST=
 
-# ===== AUTHENTICATION MODE =====
+# ============================================
-# Choose ONE of the following:
+# SINGLE-USER BASICAUTH MODE
-
+# ============================================
-# Option 1: OAuth2/OIDC (RECOMMENDED - More Secure)
+# Simplest deployment - one user, credentials in environment
-# - Requires Nextcloud OIDC app installed and configured
+# Use for: Personal instances, local development, testing
-# - Admin must enable "Dynamic Client Registration" in OIDC app settings
+#
-# - Leave NEXTCLOUD_USERNAME and NEXTCLOUD_PASSWORD empty to use OAuth mode
+# Required:
-# - OAuth client credentials are stored encrypted in SQLite (TOKEN_STORAGE_DB)
-# - Optional: Pre-register client and provide credentials (otherwise auto-registers)
-NEXTCLOUD_OIDC_CLIENT_ID=
-NEXTCLOUD_OIDC_CLIENT_SECRET=
-NEXTCLOUD_MCP_SERVER_URL=http://localhost:8000
-
-# OAuth Storage Configuration (SQLite storage for OAuth clients and refresh tokens)
-# TOKEN_ENCRYPTION_KEY: Required for encrypting OAuth client secrets and refresh tokens
-# Generate with: python -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"
-#TOKEN_ENCRYPTION_KEY=
-# TOKEN_STORAGE_DB: Path to SQLite database (default: /app/data/tokens.db)
-#TOKEN_STORAGE_DB=/app/data/tokens.db
-
-# ===== ADR-004 PROGRESSIVE CONSENT CONFIGURATION =====
-# Enable Progressive Consent mode (dual OAuth flows)
-# When enabled: Flow 1 for client auth, Flow 2 for Nextcloud resource access
-# When disabled: Uses existing hybrid flow (backward compatible)
-
-# MCP Server OAuth Client Configuration
-# The MCP server's own OAuth client credentials for Flow 2
-# If not set, will use dynamic client registration
-#MCP_SERVER_CLIENT_ID=
-#MCP_SERVER_CLIENT_SECRET=
-
-# Allowed MCP Client IDs (comma-separated list)
-# Client IDs that are allowed to authenticate in Flow 1
-# Examples: claude-desktop,continue-dev,zed-editor
-#ALLOWED_MCP_CLIENTS=claude-desktop,continue-dev,zed-editor
-
-# Token cache configuration for Token Broker Service
-# Cache TTL in seconds (default: 300 = 5 minutes)
-#TOKEN_CACHE_TTL=300
-# Early refresh threshold in seconds (default: 30)
-#TOKEN_CACHE_EARLY_REFRESH=30
-
-# Option 2: Basic Authentication (LEGACY - Less Secure)
-# - Requires username and password
-# - Credentials stored in environment variables
-# - Use only for backward compatibility or if OAuth unavailable
-# - If these are set, OAuth mode is disabled
 NEXTCLOUD_USERNAME=
 NEXTCLOUD_PASSWORD=
+#
+# Optional features (semantic search, document processing):
+# See "Optional Features" section below
 
 # ============================================
-# Document Processing Configuration
+# MULTI-USER BASICAUTH MODE
 # ============================================
-# Enable document processing (PDF, DOCX, images, etc.)
+# Users provide credentials in request headers (pass-through)
-# Set to false to disable all document processing
+# Use for: Multi-user without OAuth, simple shared deployments
-ENABLE_DOCUMENT_PROCESSING=false
+#
-
+# Required:
-# Default processor to use when multiple are available
+#ENABLE_MULTI_USER_BASIC_AUTH=true
-# Options: unstructured, tesseract, custom
+#
-DOCUMENT_PROCESSOR=unstructured
+# Optional - Background Operations (for semantic search, future features):
+# Enable background token storage using app passwords (via Astrolabe)
+# Required for semantic search in multi-user mode
+# Note: ENABLE_SEMANTIC_SEARCH automatically enables this in multi-user modes
+#ENABLE_BACKGROUND_OPERATIONS=true
+#NEXTCLOUD_OIDC_CLIENT_ID=
+#NEXTCLOUD_OIDC_CLIENT_SECRET=
+#TOKEN_ENCRYPTION_KEY=
+#TOKEN_STORAGE_DB=/app/data/tokens.db
+#
+# Optional features (semantic search, document processing):
+# See "Optional Features" section below
 
 # ============================================
-# Unstructured.io Processor
+# OAUTH SINGLE-AUDIENCE MODE (Recommended)
 # ============================================
-# Enable Unstructured processor (requires unstructured service in docker-compose)
+# Multi-user OAuth with single-audience tokens
-# This is a cloud-based/API processor supporting many document types
+# Use for: Multi-user production deployments, enhanced security
-ENABLE_UNSTRUCTURED=false
+# Tokens work for both MCP server and Nextcloud APIs (pass-through)
-
+#
-# Unstructured API endpoint
+# Required: None (uses Dynamic Client Registration if credentials not provided)
-UNSTRUCTURED_API_URL=http://unstructured:8000
+#
-
+# Optional - Pre-registered OAuth Client:
-# Request timeout in seconds (default: 120)
+# If you pre-register the client instead of using DCR:
-# OCR operations can take 30-120 seconds for large documents
+#NEXTCLOUD_OIDC_CLIENT_ID=
-UNSTRUCTURED_TIMEOUT=120
+#NEXTCLOUD_OIDC_CLIENT_SECRET=
-
+#
-# Parsing strategy: auto, fast, hi_res
+# Optional - Background Operations (for semantic search, future features):
-# - auto: Automatically choose based on document type
+# Enable refresh token storage for offline access
-# - fast: Fast parsing without OCR
+# Note: ENABLE_SEMANTIC_SEARCH automatically enables this in multi-user modes
-# - hi_res: High-resolution with OCR (slowest, most accurate)
+#ENABLE_BACKGROUND_OPERATIONS=true
-UNSTRUCTURED_STRATEGY=auto
+#TOKEN_ENCRYPTION_KEY=
-
+#TOKEN_STORAGE_DB=/app/data/tokens.db
-# OCR languages (comma-separated ISO 639-3 codes)
+#
-# Common: eng=English, deu=German, fra=French, spa=Spanish
+# Optional - Custom OIDC Discovery:
-UNSTRUCTURED_LANGUAGES=eng,deu
+# Auto-detected from NEXTCLOUD_HOST if not set
-
+#NEXTCLOUD_OIDC_DISCOVERY_URL=
-# Progress reporting interval in seconds (default: 10)
+#
-# During long-running OCR operations, progress notifications are sent to the MCP client
+# Optional - Custom Scopes:
-# at this interval to prevent timeouts and provide status updates
+# Default: openid profile email offline_access notes:* calendar:* contacts:* tables:* webdav:* deck:* cookbook:*
-PROGRESS_INTERVAL=10
+#NEXTCLOUD_OIDC_SCOPES=openid profile email notes:* calendar:*
+#
+# MCP Server URL (for OAuth redirects):
+#NEXTCLOUD_MCP_SERVER_URL=http://localhost:8000
+#
+# Optional features (semantic search, document processing):
+# See "Optional Features" section below
 
 # ============================================
-# Tesseract Processor (Local OCR)
+# OAUTH TOKEN EXCHANGE MODE (Advanced)
 # ============================================
-# Enable Tesseract processor (requires tesseract binary installed)
+# Multi-user OAuth with RFC 8693 token exchange
-# This is a local, lightweight OCR solution for images only
+# Use for: Advanced deployments requiring separate MCP and Nextcloud tokens
-ENABLE_TESSERACT=false
+# MCP tokens are separate from Nextcloud tokens
-
+#
-# Path to tesseract executable (optional, auto-detected if in PATH)
+# Required:
-#TESSERACT_CMD=/usr/bin/tesseract
+#ENABLE_TOKEN_EXCHANGE=true
-
+#
-# OCR language (e.g., eng, deu, eng+deu for multiple)
+# Optional - Pre-registered OAuth Client:
-TESSERACT_LANG=eng
+# If you pre-register the client instead of using DCR:
+#NEXTCLOUD_OIDC_CLIENT_ID=
+#NEXTCLOUD_OIDC_CLIENT_SECRET=
+#
+# Optional - Token Exchange Configuration:
+# Cache TTL in seconds (default: 300 = 5 minutes)
+#TOKEN_EXCHANGE_CACHE_TTL=300
+#
+# Optional - Background Operations:
+# Note: ENABLE_SEMANTIC_SEARCH automatically enables this in multi-user modes
+#ENABLE_BACKGROUND_OPERATIONS=true
+#TOKEN_ENCRYPTION_KEY=
+#TOKEN_STORAGE_DB=/app/data/tokens.db
+#
+# Optional - Custom OIDC Discovery:
+#NEXTCLOUD_OIDC_DISCOVERY_URL=
+#
+# MCP Server URL (for OAuth redirects):
+#NEXTCLOUD_MCP_SERVER_URL=http://localhost:8000
+#
+# Optional features (semantic search, document processing):
+# See "Optional Features" section below
 
 # ============================================
-# Custom Processor (Your own API)
+# SMITHERY STATELESS MODE
 # ============================================
-# Enable custom document processor via HTTP API
+# Stateless multi-tenant deployment for Smithery platform
-ENABLE_CUSTOM_PROCESSOR=false
+# Configuration comes from session URL parameters
-
+# No persistent storage, no OAuth, no vector sync
-# Unique name for your processor
+#
-#CUSTOM_PROCESSOR_NAME=my_ocr
+# Required: None (all config from session URL)
-
+# This mode is activated automatically when deployed to Smithery
-# Your custom processor API endpoint
-#CUSTOM_PROCESSOR_URL=http://localhost:9000/process
-
-# Optional API key for authentication
-#CUSTOM_PROCESSOR_API_KEY=your-api-key-here
-
-# Request timeout in seconds
-#CUSTOM_PROCESSOR_TIMEOUT=60
-
-# Comma-separated MIME types your processor supports
-#CUSTOM_PROCESSOR_TYPES=application/pdf,image/jpeg,image/png
 
 # ============================================
-# Semantic Search & Vector Sync Configuration
+# OPTIONAL FEATURES (All Deployment Modes)
 # ============================================
-# EXPERIMENTAL: Semantic search for Notes app (multi-app support planned)
-# Requires: Qdrant vector database + Ollama embedding service
-# Disabled by default
 
-# Enable background vector indexing
+# ===== SEMANTIC SEARCH =====
-VECTOR_SYNC_ENABLED=false
+# AI-powered semantic search across Nextcloud content
+# Requires: Qdrant vector database + embedding provider (Ollama, Bedrock, or Simple fallback)
+#
+# Enable semantic search:
+#ENABLE_SEMANTIC_SEARCH=true
+#
+# Note for Multi-User Modes:
+# ENABLE_SEMANTIC_SEARCH automatically enables background operations when needed
+# No need to set ENABLE_BACKGROUND_OPERATIONS separately
+# The server will automatically request refresh tokens and store them encrypted
+#
+# Vector Database - Choose ONE mode:
+# 1. In-memory (default): Set neither QDRANT_URL nor QDRANT_LOCATION
+# 2. Persistent local: Set QDRANT_LOCATION=/path/to/data
+# 3. Network: Set QDRANT_URL=http://qdrant:6333
+#
+#QDRANT_URL=http://qdrant:6333
+#QDRANT_LOCATION=:memory:
+#QDRANT_API_KEY=
+#QDRANT_COLLECTION=nextcloud_content
+#
+# Embedding Provider - Choose ONE:
+# 1. Ollama (recommended for local deployment):
+#OLLAMA_BASE_URL=http://ollama:11434
+#OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+#OLLAMA_VERIFY_SSL=true
+#
+# 2. Amazon Bedrock (for AWS deployments):
+#AWS_REGION=us-east-1
+#BEDROCK_EMBEDDING_MODEL=amazon.titan-embed-text-v2:0
+# Optional: AWS credentials (uses credential chain if not set)
+#AWS_ACCESS_KEY_ID=
+#AWS_SECRET_ACCESS_KEY=
+#
+# 3. Simple (automatic fallback, no configuration needed)
+# Uses basic in-memory embeddings if no provider configured
+#
+# Document Chunking:
+# Configure how documents are split before embedding
+#DOCUMENT_CHUNK_SIZE=512
+#DOCUMENT_CHUNK_OVERLAP=50
 
+# ===== SEMANTIC SEARCH TUNING =====
+# Advanced parameters for vector sync background operations
+# Only modify if you understand the implications
+#
 # Document scan interval in seconds (default: 300 = 5 minutes)
-# How often to check for new/updated documents
 #VECTOR_SYNC_SCAN_INTERVAL=300
-
+#
 # Concurrent indexing workers (default: 3)
-# Number of parallel workers for embedding generation
 #VECTOR_SYNC_PROCESSOR_WORKERS=3
-
+#
 # Max queued documents (default: 10000)
-# Maximum documents waiting to be processed
 #VECTOR_SYNC_QUEUE_MAX_SIZE=10000
 
-# ============================================
+# ===== DOCUMENT PROCESSING =====
-# Qdrant Vector Database Configuration
+# Extract text from PDFs, images, DOCX, etc. for semantic search
-# ============================================
+# Disabled by default
-# Choose ONE of three modes:
+#
-# 1. In-memory mode (default): Set neither QDRANT_URL nor QDRANT_LOCATION
+#ENABLE_DOCUMENT_PROCESSING=false
-# 2. Persistent local: Set QDRANT_LOCATION=/path/to/data
+#DOCUMENT_PROCESSOR=unstructured
-# 3. Network mode: Set QDRANT_URL=http://qdrant:6333
+#
+# Unstructured.io Processor (recommended):
+#ENABLE_UNSTRUCTURED=false
+#UNSTRUCTURED_API_URL=http://unstructured:8000
+#UNSTRUCTURED_TIMEOUT=120
+#UNSTRUCTURED_STRATEGY=auto
+#UNSTRUCTURED_LANGUAGES=eng,deu
+#PROGRESS_INTERVAL=10
+#
+# Tesseract OCR (lightweight, images only):
+#ENABLE_TESSERACT=false
+#TESSERACT_CMD=/usr/bin/tesseract
+#TESSERACT_LANG=eng
+#
+# Custom Processor (your own API):
+#ENABLE_CUSTOM_PROCESSOR=false
+#CUSTOM_PROCESSOR_NAME=my_ocr
+#CUSTOM_PROCESSOR_URL=http://localhost:9000/process
+#CUSTOM_PROCESSOR_API_KEY=
+#CUSTOM_PROCESSOR_TIMEOUT=60
+#CUSTOM_PROCESSOR_TYPES=application/pdf,image/jpeg,image/png
 
-# Network mode: URL to Qdrant service
+# ===== SECURITY & ADVANCED =====
-#QDRANT_URL=http://qdrant:6333
+# Cookie security (browser UI)
-
+# Auto-detects from NEXTCLOUD_HOST protocol if not set
-# Local mode: Path to store vectors (use :memory: for in-memory)
+#COOKIE_SECURE=true
-#QDRANT_LOCATION=:memory:
-
-# API key for network mode (optional)
-#QDRANT_API_KEY=
-
-# Collection name (optional - auto-generated if not set)
-# Auto-generation format: {deployment-id}-{model-name}
-# Allows safe model switching and multi-server deployments
-#QDRANT_COLLECTION=nextcloud_content
 
 # ============================================
-# Ollama Embedding Service Configuration
+# DEPRECATED VARIABLES (Backward Compatibility)
 # ============================================
-# Ollama endpoint for embeddings (if not set, uses SimpleEmbeddingProvider fallback)
+# These variables still work but will be removed in v1.0.0
-#OLLAMA_BASE_URL=http://ollama:11434
+# Please migrate to new names:
-
+#
-# Embedding model to use (default: nomic-embed-text, 768 dimensions)
+# Old Name                  → New Name
-# Changing this creates a new collection (requires re-embedding all documents)
+# VECTOR_SYNC_ENABLED      → ENABLE_SEMANTIC_SEARCH
-#OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+# ENABLE_OFFLINE_ACCESS    → ENABLE_BACKGROUND_OPERATIONS
-
+#
-# Verify SSL certificates (default: true)
+# Migration is optional - both old and new names work
-#OLLAMA_VERIFY_SSL=true
+# Deprecation warnings will be logged when old names are used
-
-# ============================================
-# Document Chunking Configuration
-# ============================================
-# Configure how documents are split before embedding
-
-# Words per chunk (default: 512)
-# Smaller chunks (256-384): More precise, less context, more storage
-# Larger chunks (768-1024): More context, less precise, less storage
-#DOCUMENT_CHUNK_SIZE=512
-
-# Overlapping words between chunks (default: 50)
-# Recommended: 10-20% of chunk size
-# Preserves context across chunk boundaries
-#DOCUMENT_CHUNK_OVERLAP=50

env.sample.oauth-advanced

@@ -0,0 +1,80 @@
+# ============================================
+# OAUTH TOKEN EXCHANGE QUICK START (Advanced)
+# ============================================
+# Advanced OAuth deployment with RFC 8693 token exchange
+# Use for: Deployments requiring separate MCP and Nextcloud tokens
+# Features: Dual-audience tokens, enhanced security boundaries
+#
+# Copy this file to .env and configure
+
+# ===== REQUIRED SETTINGS =====
+# Your Nextcloud instance URL (without trailing slash)
+NEXTCLOUD_HOST=https://nextcloud.example.com
+
+# Enable token exchange mode
+ENABLE_TOKEN_EXCHANGE=true
+
+# ===== REQUIRED: LEAVE USERNAME/PASSWORD EMPTY =====
+# OAuth mode activates when these are NOT set
+NEXTCLOUD_USERNAME=
+NEXTCLOUD_PASSWORD=
+
+# ===== OPTIONAL: EXPLICIT MODE DECLARATION =====
+# Recommended for clarity
+MCP_DEPLOYMENT_MODE=oauth_token_exchange
+
+# ===== OPTIONAL: PRE-REGISTERED OAUTH CLIENT =====
+# If you pre-register the OAuth client instead of using DCR:
+#NEXTCLOUD_OIDC_CLIENT_ID=your-client-id
+#NEXTCLOUD_OIDC_CLIENT_SECRET=your-client-secret
+
+# MCP Server URL (for OAuth redirects)
+NEXTCLOUD_MCP_SERVER_URL=http://localhost:8000
+
+# ===== OPTIONAL: TOKEN EXCHANGE TUNING =====
+# Cache TTL for exchanged tokens (default: 300 seconds = 5 minutes)
+TOKEN_EXCHANGE_CACHE_TTL=300
+
+# ===== OPTIONAL: SEMANTIC SEARCH =====
+# AI-powered semantic search with automatic background operation setup
+#
+# Note: ENABLE_SEMANTIC_SEARCH automatically enables background operations
+# in token exchange mode, just like in OAuth single-audience mode
+#
+ENABLE_SEMANTIC_SEARCH=true
+
+# Vector Database (required for semantic search)
+QDRANT_URL=http://qdrant:6333
+
+# Embedding Provider (required for semantic search)
+OLLAMA_BASE_URL=http://ollama:11434
+OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+
+# Token Storage (required for background operations - auto-enabled by semantic search)
+# Generate encryption key: python -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"
+TOKEN_ENCRYPTION_KEY=your-encryption-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+
+# ===== OPTIONAL: DOCUMENT PROCESSING =====
+# Extract text from PDFs, images, DOCX for semantic search
+#ENABLE_DOCUMENT_PROCESSING=true
+#ENABLE_UNSTRUCTURED=true
+#UNSTRUCTURED_API_URL=http://unstructured:8000
+
+# ===== TOKEN EXCHANGE MODE EXPLANATION =====
+# In this mode:
+# 1. MCP clients authenticate with tokens scoped to "mcp-server" audience
+# 2. Server exchanges MCP tokens for Nextcloud tokens on each request
+# 3. Provides clear separation between MCP session and Nextcloud access
+# 4. Enables fine-grained token lifecycle management
+#
+# When to use:
+# - Strict security requirements (separate token contexts)
+# - Complex multi-service architectures
+# - Need independent token expiration policies
+#
+# When NOT to use:
+# - Simple deployments (use oauth_single_audience instead)
+# - High-performance requirements (token exchange adds latency)
+
+# For more configuration options, see env.sample

env.sample.oauth-multi-user

@@ -0,0 +1,77 @@
+# ============================================
+# OAUTH MULTI-USER QUICK START (Recommended)
+# ============================================
+# Multi-user deployment with OAuth authentication
+# Use for: Multi-user production deployments, enhanced security
+# Features: Single-audience tokens, automatic client registration (DCR)
+#
+# Copy this file to .env and configure
+
+# ===== REQUIRED SETTINGS =====
+# Your Nextcloud instance URL (without trailing slash)
+NEXTCLOUD_HOST=https://nextcloud.example.com
+
+# ===== REQUIRED: LEAVE USERNAME/PASSWORD EMPTY =====
+# OAuth mode activates when these are NOT set
+NEXTCLOUD_USERNAME=
+NEXTCLOUD_PASSWORD=
+
+# ===== OPTIONAL: EXPLICIT MODE DECLARATION =====
+# Recommended for clarity
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# ===== OPTIONAL: PRE-REGISTERED OAUTH CLIENT =====
+# If you pre-register the OAuth client instead of using DCR:
+#NEXTCLOUD_OIDC_CLIENT_ID=your-client-id
+#NEXTCLOUD_OIDC_CLIENT_SECRET=your-client-secret
+
+# MCP Server URL (for OAuth redirects)
+NEXTCLOUD_MCP_SERVER_URL=http://localhost:8000
+
+# ===== OPTIONAL: SEMANTIC SEARCH (Recommended) =====
+# AI-powered semantic search with automatic background operation setup
+#
+# When you enable semantic search in multi-user mode:
+# 1. ENABLE_SEMANTIC_SEARCH automatically enables background operations
+# 2. Server requests refresh tokens for offline indexing
+# 3. Tokens are stored encrypted in TOKEN_STORAGE_DB
+# 4. No need to set ENABLE_BACKGROUND_OPERATIONS separately!
+#
+ENABLE_SEMANTIC_SEARCH=true
+
+# Vector Database (required for semantic search)
+QDRANT_URL=http://qdrant:6333
+# OR for in-memory mode:
+#QDRANT_LOCATION=:memory:
+
+# Embedding Provider (required for semantic search)
+# Option 1: Ollama (recommended for local deployment)
+OLLAMA_BASE_URL=http://ollama:11434
+OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+
+# Option 2: Amazon Bedrock (for AWS deployments)
+#AWS_REGION=us-east-1
+#BEDROCK_EMBEDDING_MODEL=amazon.titan-embed-text-v2:0
+
+# Token Storage (required for background operations - auto-enabled by semantic search)
+# Generate encryption key: python -c "from cryptography.fernet import Fernet; print(Fernet.generate_key().decode())"
+TOKEN_ENCRYPTION_KEY=your-encryption-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+
+# ===== OPTIONAL: DOCUMENT PROCESSING =====
+# Extract text from PDFs, images, DOCX for semantic search
+#ENABLE_DOCUMENT_PROCESSING=true
+#ENABLE_UNSTRUCTURED=true
+#UNSTRUCTURED_API_URL=http://unstructured:8000
+
+# ===== SUMMARY OF AUTO-ENABLEMENT =====
+# With ENABLE_SEMANTIC_SEARCH=true in OAuth mode:
+# ✅ Background operations enabled automatically
+# ✅ Refresh token storage enabled automatically
+# ✅ OAuth credentials required (DCR or pre-registered)
+# ✅ Encryption key required for token storage
+#
+# You only need to set ENABLE_SEMANTIC_SEARCH and provide the required
+# infrastructure (Qdrant, Ollama, encryption key). The rest is automatic!
+
+# For more advanced configuration, see env.sample

env.sample.single-user

@@ -0,0 +1,37 @@
+# ============================================
+# SINGLE-USER BASICAUTH QUICK START
+# ============================================
+# Simplest deployment mode - one user, credentials in environment
+# Use for: Personal instances, local development, testing
+#
+# Copy this file to .env and fill in your credentials
+
+# ===== REQUIRED SETTINGS =====
+# Your Nextcloud instance URL (without trailing slash)
+NEXTCLOUD_HOST=http://localhost:8080
+
+# Your Nextcloud credentials
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+
+# ===== OPTIONAL: EXPLICIT MODE DECLARATION =====
+# Recommended to avoid ambiguity
+MCP_DEPLOYMENT_MODE=single_user_basic
+
+# ===== OPTIONAL: SEMANTIC SEARCH =====
+# Uncomment to enable AI-powered semantic search
+# Requires: Qdrant + embedding provider (Ollama or Bedrock)
+#
+#ENABLE_SEMANTIC_SEARCH=true
+#QDRANT_LOCATION=:memory:
+#OLLAMA_BASE_URL=http://ollama:11434
+#OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+
+# ===== OPTIONAL: DOCUMENT PROCESSING =====
+# Extract text from PDFs, images, DOCX for semantic search
+#ENABLE_DOCUMENT_PROCESSING=true
+#ENABLE_UNSTRUCTURED=true
+#UNSTRUCTURED_API_URL=http://unstructured:8000
+
+# That's it! Single-user mode is the simplest to configure.
+# For more options, see env.sample

nextcloud_mcp_server/alembic/env.py

@@ -0,0 +1,133 @@
+"""Alembic environment configuration for nextcloud-mcp-server.
+
+This module configures how Alembic runs database migrations for the
+token storage database. It supports both online and offline migration modes.
+
+Uses anyio for async operations, consistent with the project's async patterns.
+"""
+
+import logging
+from pathlib import Path
+
+import anyio
+from sqlalchemy import pool
+from sqlalchemy.engine import Connection
+from sqlalchemy.ext.asyncio import async_engine_from_config
+
+from alembic import context
+
+# Configure logging
+logger = logging.getLogger("alembic.env")
+
+# This is the Alembic Config object, which provides
+# access to the values within the .ini file in use.
+config = context.config
+
+# Update script location to point to package location
+# This allows alembic to find migrations when installed in site-packages
+script_location = Path(__file__).parent
+config.set_main_option("script_location", str(script_location))
+
+# We don't use SQLAlchemy models, so target_metadata is None
+# Migrations will be written manually using op.execute() for raw SQL
+target_metadata = None
+
+
+def get_database_url() -> str:
+    """
+    Get the database URL from Alembic config or environment.
+
+    The URL can be set in alembic.ini or passed via -x database_url=...
+    when running Alembic commands.
+
+    Returns:
+        Database URL (SQLite URL format)
+    """
+    # Check if URL is passed via -x database_url=...
+    url = context.get_x_argument(as_dictionary=True).get("database_url")
+
+    if not url:
+        # Fall back to alembic.ini configuration
+        url = config.get_main_option("sqlalchemy.url")
+
+    if not url:
+        # Default to /app/data/tokens.db for Docker deployments
+        db_path = Path("/app/data/tokens.db")
+        url = f"sqlite+aiosqlite:///{db_path}"
+        logger.warning(
+            f"No database URL configured, using default: {url}. "
+            "Set sqlalchemy.url in alembic.ini or pass -x database_url=..."
+        )
+
+    return url
+
+
+def run_migrations_offline() -> None:
+    """Run migrations in 'offline' mode.
+
+    This configures the context with just a URL and not an Engine,
+    though an Engine is acceptable here as well. By skipping the
+    Engine creation we don't even need a DBAPI to be available.
+
+    Calls to context.execute() here emit the given string to the
+    script output.
+
+    This mode is useful for generating SQL scripts without database access.
+    """
+    url = get_database_url()
+    context.configure(
+        url=url,
+        target_metadata=target_metadata,
+        literal_binds=True,
+        dialect_opts={"paramstyle": "named"},
+    )
+
+    with context.begin_transaction():
+        context.run_migrations()
+
+
+def do_run_migrations(connection: Connection) -> None:
+    """Execute migrations within a database connection."""
+    context.configure(connection=connection, target_metadata=target_metadata)
+
+    with context.begin_transaction():
+        context.run_migrations()
+
+
+async def run_async_migrations() -> None:
+    """Run migrations in 'online' mode with async support.
+
+    In this scenario we create an async Engine and associate
+    a connection with the context.
+    """
+    # Get database URL and update config
+    url = get_database_url()
+    config.set_main_option("sqlalchemy.url", url)
+
+    # Create async engine
+    connectable = async_engine_from_config(
+        config.get_section(config.config_ini_section, {}),
+        prefix="sqlalchemy.",
+        poolclass=pool.NullPool,  # Don't pool connections for migrations
+    )
+
+    async with connectable.connect() as connection:
+        await connection.run_sync(do_run_migrations)
+
+    await connectable.dispose()
+
+
+def run_migrations_online() -> None:
+    """Run migrations in 'online' mode.
+
+    This function is called from storage.py's initialize() method via
+    anyio.to_thread.run_sync(), so it always runs in a worker thread
+    with its own event loop. We can safely use anyio.run() here.
+    """
+    anyio.run(run_async_migrations)
+
+
+if context.is_offline_mode():
+    run_migrations_offline()
+else:
+    run_migrations_online()

nextcloud_mcp_server/alembic/versions/20251217_2200_001_initial_schema.py

@@ -0,0 +1,185 @@
+"""Initial schema for token storage database
+
+This migration creates the initial database schema including:
+- refresh_tokens: OAuth refresh tokens and user profiles
+- audit_logs: Audit trail for security events
+- oauth_clients: OAuth client credentials (DCR)
+- oauth_sessions: OAuth flow session state (ADR-004 Progressive Consent)
+- registered_webhooks: Webhook registration tracking (both OAuth and BasicAuth)
+- schema_version: Legacy schema version tracking (deprecated, use alembic_version)
+
+Revision ID: 001
+Revises:
+Create Date: 2025-12-17 22:00:00.000000
+
+"""
+
+from alembic import op
+
+# revision identifiers, used by Alembic.
+revision = "001"
+down_revision = None
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    """Create initial database schema."""
+
+    # Refresh tokens table (OAuth mode only, for background jobs)
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS refresh_tokens (
+            user_id TEXT PRIMARY KEY,
+            encrypted_token BLOB NOT NULL,
+            expires_at INTEGER,
+            created_at INTEGER NOT NULL,
+            updated_at INTEGER NOT NULL,
+            -- ADR-004 Progressive Consent fields
+            flow_type TEXT DEFAULT 'hybrid',
+            token_audience TEXT DEFAULT 'nextcloud',
+            provisioned_at INTEGER,
+            provisioning_client_id TEXT,
+            scopes TEXT,
+            -- Browser session profile cache
+            user_profile TEXT,
+            profile_cached_at INTEGER
+        )
+        """
+    )
+
+    # Audit logs table (both OAuth and BasicAuth modes)
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS audit_logs (
+            id INTEGER PRIMARY KEY AUTOINCREMENT,
+            timestamp INTEGER NOT NULL,
+            event TEXT NOT NULL,
+            user_id TEXT NOT NULL,
+            resource_type TEXT,
+            resource_id TEXT,
+            auth_method TEXT,
+            hostname TEXT
+        )
+        """
+    )
+
+    # Index on audit logs for efficient queries
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS idx_audit_user_timestamp
+        ON audit_logs(user_id, timestamp)
+        """
+    )
+
+    # OAuth client credentials storage (OAuth mode only)
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS oauth_clients (
+            id INTEGER PRIMARY KEY,
+            client_id TEXT UNIQUE NOT NULL,
+            encrypted_client_secret BLOB NOT NULL,
+            client_id_issued_at INTEGER NOT NULL,
+            client_secret_expires_at INTEGER NOT NULL,
+            redirect_uris TEXT NOT NULL,
+            encrypted_registration_access_token BLOB,
+            registration_client_uri TEXT,
+            created_at INTEGER NOT NULL,
+            updated_at INTEGER NOT NULL
+        )
+        """
+    )
+
+    # OAuth flow sessions (ADR-004 Progressive Consent)
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS oauth_sessions (
+            session_id TEXT PRIMARY KEY,
+            client_id TEXT,
+            client_redirect_uri TEXT NOT NULL,
+            state TEXT,
+            code_challenge TEXT,
+            code_challenge_method TEXT,
+            mcp_authorization_code TEXT UNIQUE,
+            idp_access_token TEXT,
+            idp_refresh_token TEXT,
+            user_id TEXT,
+            created_at INTEGER NOT NULL,
+            expires_at INTEGER NOT NULL,
+            -- ADR-004 Progressive Consent fields
+            flow_type TEXT DEFAULT 'hybrid',
+            requested_scopes TEXT,
+            granted_scopes TEXT,
+            is_provisioning BOOLEAN DEFAULT FALSE
+        )
+        """
+    )
+
+    # Index for MCP authorization code lookups
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS idx_oauth_sessions_mcp_code
+        ON oauth_sessions(mcp_authorization_code)
+        """
+    )
+
+    # Legacy schema version tracking table
+    # NOTE: This is deprecated in favor of Alembic's alembic_version table
+    # Kept for backward compatibility with pre-Alembic databases
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS schema_version (
+            version INTEGER PRIMARY KEY,
+            applied_at REAL NOT NULL
+        )
+        """
+    )
+
+    # Registered webhooks tracking (both BasicAuth and OAuth modes)
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS registered_webhooks (
+            id INTEGER PRIMARY KEY AUTOINCREMENT,
+            webhook_id INTEGER NOT NULL UNIQUE,
+            preset_id TEXT NOT NULL,
+            created_at REAL NOT NULL
+        )
+        """
+    )
+
+    # Indexes for efficient webhook queries
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS idx_webhooks_preset
+        ON registered_webhooks(preset_id)
+        """
+    )
+
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS idx_webhooks_created
+        ON registered_webhooks(created_at)
+        """
+    )
+
+
+def downgrade() -> None:
+    """Drop all tables and indexes.
+
+    WARNING: This will destroy all data in the database!
+    Use with extreme caution.
+    """
+
+    # Drop indexes first
+    op.execute("DROP INDEX IF EXISTS idx_webhooks_created")
+    op.execute("DROP INDEX IF EXISTS idx_webhooks_preset")
+    op.execute("DROP INDEX IF EXISTS idx_oauth_sessions_mcp_code")
+    op.execute("DROP INDEX IF EXISTS idx_audit_user_timestamp")
+
+    # Drop tables
+    op.execute("DROP TABLE IF EXISTS registered_webhooks")
+    op.execute("DROP TABLE IF EXISTS schema_version")
+    op.execute("DROP TABLE IF EXISTS oauth_sessions")
+    op.execute("DROP TABLE IF EXISTS oauth_clients")
+    op.execute("DROP TABLE IF EXISTS audit_logs")
+    op.execute("DROP TABLE IF EXISTS refresh_tokens")

nextcloud_mcp_server/api/__init__.py

@@ -0,0 +1,6 @@
+"""Management API for Nextcloud MCP Server.
+
+Provides REST endpoints for the Nextcloud PHP app to query server status,
+user sessions, and vector sync metrics. All endpoints use OAuth bearer token
+authentication via the UnifiedTokenVerifier.
+"""

nextcloud_mcp_server/app.py

@@ -1,11 +1,12 @@
 import logging
 import os
 import time
+import traceback
 from collections.abc import AsyncIterator
 from contextlib import AsyncExitStack, asynccontextmanager
 from contextvars import ContextVar
 from dataclasses import dataclass
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING, Optional, cast
 
 from opentelemetry.instrumentation.httpx import HTTPXClientInstrumentor
 
@@ -19,6 +20,7 @@ import httpx
 from anyio.streams.memory import MemoryObjectReceiveStream, MemoryObjectSendStream
 from mcp.server.auth.settings import AuthSettings
 from mcp.server.fastmcp import Context, FastMCP
+from mcp.server.transport_security import TransportSecuritySettings
 from pydantic import AnyHttpUrl
 from starlette.applications import Starlette
 from starlette.middleware.authentication import AuthenticationMiddleware
@@ -40,10 +42,14 @@ from nextcloud_mcp_server.auth.unified_verifier import UnifiedTokenVerifier
 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import (
     DeploymentMode,
-    get_deployment_mode,
     get_document_processor_config,
     get_settings,
 )
+from nextcloud_mcp_server.config_validators import (
+    AuthMode,
+    get_mode_summary,
+    validate_configuration,
+)
 from nextcloud_mcp_server.context import get_client as get_nextcloud_client
 from nextcloud_mcp_server.document_processors import get_registry
 from nextcloud_mcp_server.observability import (
@@ -60,6 +66,7 @@ from nextcloud_mcp_server.server import (
     configure_contacts_tools,
     configure_cookbook_tools,
     configure_deck_tools,
+    configure_news_tools,
     configure_notes_tools,
     configure_semantic_tools,
     configure_sharing_tools,
@@ -349,6 +356,52 @@ def get_smithery_session_config() -> dict | None:
     return _smithery_session_config.get()
 
 
+class BasicAuthMiddleware:
+    """Middleware to extract BasicAuth credentials from Authorization header.
+
+    For multi-user BasicAuth pass-through mode, this middleware extracts
+    username/password from the Authorization: Basic header and stores them
+    in the request state for use by the context layer.
+
+    The credentials are NOT stored persistently - they are passed through
+    directly to Nextcloud APIs for each request (stateless).
+    """
+
+    def __init__(self, app: ASGIApp):
+        self.app = app
+
+    async def __call__(
+        self, scope: StarletteScope, receive: Receive, send: Send
+    ) -> None:
+        if scope["type"] == "http":
+            # Extract Authorization header
+            headers = dict(scope.get("headers", []))
+            auth_header = headers.get(b"authorization", b"")
+
+            if auth_header.startswith(b"Basic "):
+                try:
+                    import base64
+
+                    # Decode base64(username:password)
+                    encoded = auth_header[6:]  # Skip "Basic "
+                    decoded = base64.b64decode(encoded).decode("utf-8")
+                    username, password = decoded.split(":", 1)
+
+                    # Store in request state
+                    scope.setdefault("state", {})
+                    scope["state"]["basic_auth"] = {
+                        "username": username,
+                        "password": password,
+                    }
+                    logger.debug(
+                        f"BasicAuth credentials extracted for user: {username}"
+                    )
+                except Exception as e:
+                    logger.warning(f"Failed to extract BasicAuth credentials: {e}")
+
+        await self.app(scope, receive, send)
+
+
 class SmitheryConfigMiddleware:
     """Middleware to extract Smithery config from URL query parameters.
 
@@ -421,41 +474,6 @@ async def app_lifespan_smithery(server: FastMCP) -> AsyncIterator[SmitheryAppCon
         logger.info("Shutting down Smithery stateless mode")
 
 
-def is_oauth_mode() -> bool:
-    """
-    Determine if OAuth mode should be used.
-
-    OAuth mode is enabled when:
-    - NEXTCLOUD_USERNAME and NEXTCLOUD_PASSWORD are NOT set
-    - AND we are NOT in Smithery stateless mode
-    - Or explicitly enabled via configuration
-
-    Returns:
-        True if OAuth mode, False if BasicAuth mode
-    """
-    # ADR-016: Smithery stateless mode uses per-request BasicAuth from session config
-    # It's not OAuth mode even though env credentials aren't set
-    deployment_mode = get_deployment_mode()
-    if deployment_mode == DeploymentMode.SMITHERY_STATELESS:
-        logger.info(
-            "BasicAuth mode (Smithery stateless - credentials from session config)"
-        )
-        return False
-
-    username = os.getenv("NEXTCLOUD_USERNAME")
-    password = os.getenv("NEXTCLOUD_PASSWORD")
-
-    # If both username and password are set, use BasicAuth
-    if username and password:
-        logger.info(
-            "BasicAuth mode detected (NEXTCLOUD_USERNAME and NEXTCLOUD_PASSWORD set)"
-        )
-        return False
-
-    logger.info("OAuth mode detected (NEXTCLOUD_USERNAME/PASSWORD not set)")
-    return True
-
-
 async def load_oauth_client_credentials(
     nextcloud_host: str, registration_endpoint: str | None
 ) -> tuple[str, str]:
@@ -514,7 +532,7 @@ async def load_oauth_client_credentials(
         # and the authorization server will limit them to these allowed scopes.
         #
         # The PRM endpoint advertises the same scopes dynamically via @require_scopes decorators.
-        dcr_scopes = "openid profile email notes:read notes:write calendar:read calendar:write todo:read todo:write contacts:read contacts:write cookbook:read cookbook:write deck:read deck:write tables:read tables:write files:read files:write sharing:read sharing:write"
+        dcr_scopes = "openid profile email notes:read notes:write calendar:read calendar:write todo:read todo:write contacts:read contacts:write cookbook:read cookbook:write deck:read deck:write tables:read tables:write files:read files:write sharing:read sharing:write news:read news:write"
 
         # Add offline_access scope if refresh tokens are enabled
         enable_offline_access = os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() in (
@@ -576,17 +594,31 @@ async def app_lifespan_basic(server: FastMCP) -> AsyncIterator[AppContext]:
     """
     Manage application lifecycle for BasicAuth mode (FastMCP session lifespan).
 
-    Creates a single Nextcloud client with basic authentication
+    For single-user mode: Creates a single Nextcloud client with basic authentication
     that is shared across all requests within a session.
 
+    For multi-user mode: No shared client - clients created per-request by BasicAuthMiddleware.
+
     Note: Background tasks (scanner, processor) are started at server level
     in starlette_lifespan, not here. This lifespan runs per-session.
     """
-    logger.info("Starting MCP session in BasicAuth mode")
+    settings = get_settings()
-    logger.info("Creating Nextcloud client with BasicAuth")
+    is_multi_user = settings.enable_multi_user_basic_auth
 
-    client = NextcloudClient.from_env()
+    logger.info(
-    logger.info("Client initialization complete")
+        f"Starting MCP session in {'multi-user' if is_multi_user else 'single-user'} BasicAuth mode"
+    )
+
+    # Only create shared client for single-user mode
+    client = None
+    if not is_multi_user:
+        logger.info("Creating shared Nextcloud client with BasicAuth")
+        client = NextcloudClient.from_env()
+        logger.info("Client initialization complete")
+    else:
+        logger.info(
+            "Multi-user mode - clients created per-request from BasicAuth headers"
+        )
 
     # Initialize persistent storage (for webhook tracking and future features)
     from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
@@ -602,7 +634,7 @@ async def app_lifespan_basic(server: FastMCP) -> AsyncIterator[AppContext]:
     # Include vector sync state from module singleton (set by starlette_lifespan)
     try:
         yield AppContext(
-            client=client,
+            client=client,  # type: ignore[arg-type]  # None in multi-user mode
             storage=storage,
             document_send_stream=_vector_sync_state.document_send_stream,
             document_receive_stream=_vector_sync_state.document_receive_stream,
@@ -611,7 +643,8 @@ async def app_lifespan_basic(server: FastMCP) -> AsyncIterator[AppContext]:
         )
     finally:
         logger.info("Shutting down BasicAuth session")
-        await client.close()
+        if client is not None:
+            await client.close()
 
 
 async def setup_oauth_config():
@@ -674,6 +707,29 @@ async def setup_oauth_config():
         logger.info(f"OIDC_JWKS_URI override: {jwks_uri} → {jwks_uri_override}")
         jwks_uri = jwks_uri_override
 
+    # Rewrite discovered endpoint URLs from public issuer to internal host
+    # This is needed when OIDC discovery returns public URLs (e.g., http://localhost:8080)
+    # but the server needs to access them via internal docker network (e.g., http://app:80)
+    from urllib.parse import urlparse
+
+    issuer_parsed = urlparse(issuer)
+    nextcloud_parsed = urlparse(nextcloud_host)
+    issuer_base = f"{issuer_parsed.scheme}://{issuer_parsed.netloc}"
+    nextcloud_base = f"{nextcloud_parsed.scheme}://{nextcloud_parsed.netloc}"
+
+    if issuer_base != nextcloud_base:
+        logger.info(f"Rewriting OIDC endpoints: {issuer_base} → {nextcloud_base}")
+
+        def rewrite_url(url: str | None) -> str | None:
+            if url and url.startswith(issuer_base):
+                return url.replace(issuer_base, nextcloud_base, 1)
+            return url
+
+        userinfo_uri = rewrite_url(userinfo_uri) or userinfo_uri
+        jwks_uri = rewrite_url(jwks_uri)
+        introspection_uri = rewrite_url(introspection_uri)
+        registration_endpoint = rewrite_url(registration_endpoint)
+
     logger.info("OIDC endpoints discovered:")
     logger.info(f"  Issuer: {issuer}")
     logger.info(f"  Userinfo: {userinfo_uri}")
@@ -685,8 +741,6 @@ async def setup_oauth_config():
     # Auto-detect provider mode based on issuer
     # External IdP mode: issuer doesn't match Nextcloud host
     # Normalize URLs for comparison (handle port differences like :80 for HTTP)
-    from urllib.parse import urlparse
-
     def normalize_url(url: str) -> str:
         """Normalize URL by removing default ports (80 for HTTP, 443 for HTTPS)."""
         parsed = urlparse(url)
@@ -702,7 +756,16 @@ async def setup_oauth_config():
     issuer_normalized = normalize_url(issuer)
     nextcloud_normalized = normalize_url(nextcloud_host)
 
-    is_external_idp = not issuer_normalized.startswith(nextcloud_normalized)
+    # Use NEXTCLOUD_PUBLIC_ISSUER_URL for IdP detection when set
+    # This handles the case where MCP server accesses Nextcloud via internal URL (http://app:80)
+    # but the issuer in OIDC discovery is the public URL (http://localhost:8080)
+    public_issuer_for_detection = os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL")
+    if public_issuer_for_detection:
+        comparison_issuer = normalize_url(public_issuer_for_detection)
+    else:
+        comparison_issuer = nextcloud_normalized
+
+    is_external_idp = not issuer_normalized.startswith(comparison_issuer)
 
     if is_external_idp:
         oauth_provider = "external"  # Could be Keycloak, Auth0, Okta, etc.
@@ -714,6 +777,28 @@ async def setup_oauth_config():
         oauth_provider = "nextcloud"
         logger.info("✓ Detected integrated mode (Nextcloud OIDC app)")
 
+        # For integrated mode, rewrite OIDC endpoints to use internal URL
+        # The discovery document returns external URLs (http://localhost:8080)
+        # but the MCP server needs internal URLs (http://app:80) for backend requests
+        if jwks_uri and not os.getenv("OIDC_JWKS_URI"):
+            internal_jwks_uri = f"{nextcloud_host}/apps/oidc/jwks"
+            logger.info(
+                f"  Auto-rewriting JWKS URI for internal access: {jwks_uri} → {internal_jwks_uri}"
+            )
+            jwks_uri = internal_jwks_uri
+        if introspection_uri and not os.getenv("OIDC_INTROSPECTION_URI"):
+            internal_introspection_uri = f"{nextcloud_host}/apps/oidc/introspect"
+            logger.info(
+                f"  Auto-rewriting introspection URI for internal access: {introspection_uri} → {internal_introspection_uri}"
+            )
+            introspection_uri = internal_introspection_uri
+        if userinfo_uri:
+            internal_userinfo_uri = f"{nextcloud_host}/apps/oidc/userinfo"
+            logger.info(
+                f"  Auto-rewriting userinfo URI for internal access: {userinfo_uri} → {internal_userinfo_uri}"
+            )
+            userinfo_uri = internal_userinfo_uri
+
     # Check if offline access (refresh tokens) is enabled
     enable_offline_access = os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() in (
         "true",
@@ -931,6 +1016,33 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
     # Initialize observability (logging will be configured by uvicorn)
     settings = get_settings()
 
+    # Validate configuration and detect deployment mode
+    mode, config_errors = validate_configuration(settings)
+
+    if config_errors:
+        error_msg = (
+            f"Configuration validation failed for {mode.value} mode:\n"
+            + "\n".join(f"  - {err}" for err in config_errors)
+            + "\n\n"
+            + get_mode_summary(mode)
+        )
+        logger.error(error_msg)
+        raise ValueError(error_msg)
+
+    logger.info(f"✅ Configuration validated successfully for {mode.value} mode")
+    logger.debug(f"Mode details:\n{get_mode_summary(mode)}")
+
+    # Derive helper variables for backward compatibility with existing code
+    oauth_enabled = mode in (
+        AuthMode.OAUTH_SINGLE_AUDIENCE,
+        AuthMode.OAUTH_TOKEN_EXCHANGE,
+    )
+    deployment_mode = (
+        DeploymentMode.SMITHERY_STATELESS
+        if mode == AuthMode.SMITHERY_STATELESS
+        else DeploymentMode.SELF_HOSTED
+    )
+
     # Setup Prometheus metrics (always enabled by default)
     if settings.metrics_enabled:
         setup_metrics(port=settings.metrics_port)
@@ -954,11 +1066,77 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
             "OpenTelemetry tracing disabled (set OTEL_EXPORTER_OTLP_ENDPOINT to enable)"
         )
 
-    # Determine authentication mode and deployment mode
+    # Initialize OAuth credentials for multi-user modes that need background operations
-    oauth_enabled = is_oauth_mode()
+    # This must happen BEFORE uvicorn starts (same lifecycle point as OAuth modes)
-    deployment_mode = get_deployment_mode()
+    # to avoid async context issues
+    multi_user_basic_oauth_creds: tuple[str, str] | None = None
 
-    if oauth_enabled:
+    if (
+        mode == AuthMode.MULTI_USER_BASIC
+        and settings.vector_sync_enabled
+        and settings.enable_offline_access
+    ):
+        print(
+            f"DEBUG: Multi-user BasicAuth mode detected, vector_sync={settings.vector_sync_enabled}, offline_access={settings.enable_offline_access}"
+        )
+        logger.info(
+            "Multi-user BasicAuth with vector sync - checking for OAuth credentials"
+        )
+
+        # Check for static credentials first
+        static_client_id = os.getenv("NEXTCLOUD_OIDC_CLIENT_ID")
+        static_client_secret = os.getenv("NEXTCLOUD_OIDC_CLIENT_SECRET")
+
+        if static_client_id and static_client_secret:
+            print("DEBUG: Using static OAuth credentials")
+            logger.info("Using static OAuth credentials for background operations")
+            multi_user_basic_oauth_creds = (static_client_id, static_client_secret)
+        else:
+            # Perform DCR before uvicorn starts (same lifecycle as OAuth modes)
+            print("DEBUG: No static credentials, attempting DCR...")
+            logger.info(
+                "OAuth credentials not configured - attempting Dynamic Client Registration..."
+            )
+
+            import anyio
+
+            async def setup_multi_user_basic_dcr():
+                """Setup DCR for multi-user BasicAuth background operations."""
+                # Construct registration endpoint directly from nextcloud_host
+                # Standard RFC 7591 endpoint pattern for Nextcloud OIDC
+                # This avoids relying on discovery doc which may use public URLs unreachable from containers
+                registration_endpoint = f"{settings.nextcloud_host}/apps/oidc/register"
+                logger.info(
+                    f"Attempting Dynamic Client Registration at: {registration_endpoint}"
+                )
+
+                # Perform DCR
+                try:
+                    # Assert nextcloud_host is not None (required for multi-user mode)
+                    assert settings.nextcloud_host is not None, (
+                        "NEXTCLOUD_HOST is required"
+                    )
+
+                    client_id, client_secret = await load_oauth_client_credentials(
+                        nextcloud_host=settings.nextcloud_host,
+                        registration_endpoint=registration_endpoint,
+                    )
+                    logger.info(
+                        f"✓ Dynamic Client Registration successful for background operations "
+                        f"(client_id: {client_id[:16]}...)"
+                    )
+                    return (client_id, client_secret)
+                except Exception as e:
+                    logger.error(f"Dynamic Client Registration failed: {e}")
+                    logger.debug(f"Full traceback:\n{traceback.format_exc()}")
+                    logger.warning("Background vector sync will be disabled.")
+                    return None
+
+            # Run DCR synchronously before uvicorn starts
+            multi_user_basic_oauth_creds = anyio.run(setup_multi_user_basic_dcr)
+
+    # Create MCP server based on detected mode
+    if mode in (AuthMode.OAUTH_SINGLE_AUDIENCE, AuthMode.OAUTH_TOKEN_EXCHANGE):
         logger.info("Configuring MCP server for OAuth mode")
         # Asynchronously get the OAuth configuration
         import anyio
@@ -1015,19 +1193,38 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
             lifespan=oauth_lifespan,
             token_verifier=token_verifier,
             auth=auth_settings,
+            # Disable DNS rebinding protection for containerized deployments (k8s, Docker)
+            # MCP 1.23+ auto-enables this for localhost, breaking k8s service DNS names
+            transport_security=TransportSecuritySettings(
+                enable_dns_rebinding_protection=False
+            ),
+        )
+    elif mode == AuthMode.SMITHERY_STATELESS:
+        logger.info("Configuring MCP server for Smithery stateless mode")
+        # json_response=True returns plain JSON-RPC instead of SSE format,
+        # required for Smithery scanner compatibility
+        mcp = FastMCP(
+            "Nextcloud MCP",
+            lifespan=app_lifespan_smithery,
+            json_response=True,
+            # Disable DNS rebinding protection for containerized deployments (k8s, Docker)
+            # MCP 1.23+ auto-enables this for localhost, breaking k8s service DNS names
+            transport_security=TransportSecuritySettings(
+                enable_dns_rebinding_protection=False
+            ),
         )
     else:
-        # ADR-016: Use Smithery lifespan for stateless mode, BasicAuth otherwise
+        # BasicAuth modes (single-user or multi-user)
-        if deployment_mode == DeploymentMode.SMITHERY_STATELESS:
+        logger.info(f"Configuring MCP server for {mode.value} mode")
-            logger.info("Configuring MCP server for Smithery stateless mode")
+        mcp = FastMCP(
-            # json_response=True returns plain JSON-RPC instead of SSE format,
+            "Nextcloud MCP",
-            # required for Smithery scanner compatibility
+            lifespan=app_lifespan_basic,
-            mcp = FastMCP(
+            # Disable DNS rebinding protection for containerized deployments (k8s, Docker)
-                "Nextcloud MCP", lifespan=app_lifespan_smithery, json_response=True
+            # MCP 1.23+ auto-enables this for localhost, breaking k8s service DNS names
-            )
+            transport_security=TransportSecuritySettings(
-        else:
+                enable_dns_rebinding_protection=False
-            logger.info("Configuring MCP server for BasicAuth mode")
+            ),
-            mcp = FastMCP("Nextcloud MCP", lifespan=app_lifespan_basic)
+        )
 
     @mcp.resource("nc://capabilities")
     async def nc_get_capabilities():
@@ -1046,6 +1243,7 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
         "contacts": configure_contacts_tools,
         "cookbook": configure_cookbook_tools,
         "deck": configure_deck_tools,
+        "news": configure_news_tools,
     }
 
     # If no specific apps are specified, enable all
@@ -1064,8 +1262,6 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
 
     # Register semantic search tools (cross-app feature)
     # ADR-016: Skip in Smithery stateless mode (no vector database)
-    settings = get_settings()
-    deployment_mode = get_deployment_mode()
     if deployment_mode == DeploymentMode.SMITHERY_STATELESS:
         logger.info("Skipping semantic search tools (Smithery stateless mode)")
     elif settings.vector_sync_enabled:
@@ -1152,13 +1348,20 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
         # Set OAuth context for OAuth login routes (ADR-004)
         if oauth_enabled:
             # Prepare OAuth config from setup_oauth_config closure variables
+            # Get nextcloud_host from settings (it was validated as required)
+            nextcloud_host_for_context = settings.nextcloud_host
+            if not nextcloud_host_for_context:
+                raise ValueError("NEXTCLOUD_HOST is required for OAuth mode")
+
             mcp_server_url = os.getenv(
                 "NEXTCLOUD_MCP_SERVER_URL", "http://localhost:8000"
             )
-            nextcloud_resource_uri = os.getenv("NEXTCLOUD_RESOURCE_URI", nextcloud_host)
+            nextcloud_resource_uri = os.getenv(
+                "NEXTCLOUD_RESOURCE_URI", nextcloud_host_for_context
+            )
             discovery_url = os.getenv(
                 "OIDC_DISCOVERY_URL",
-                f"{nextcloud_host}/.well-known/openid-configuration",
+                f"{nextcloud_host_for_context}/.well-known/openid-configuration",
             )
             scopes = os.getenv("NEXTCLOUD_OIDC_SCOPES", "")
 
@@ -1172,7 +1375,7 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
                     "client_id": client_id,  # From setup_oauth_config (DCR or static)
                     "client_secret": client_secret,  # From setup_oauth_config (DCR or static)
                     "scopes": scopes,
-                    "nextcloud_host": nextcloud_host,
+                    "nextcloud_host": nextcloud_host_for_context,
                     "nextcloud_resource_uri": nextcloud_resource_uri,
                     "oauth_provider": oauth_provider,
                 },
@@ -1184,7 +1387,8 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
             # We need to find it in the mounted routes
             for route in app.routes:
                 if isinstance(route, Mount) and route.path == "/app":
-                    route.app.state.oauth_context = oauth_context_dict
+                    browser_app = cast(Starlette, route.app)
+                    browser_app.state.oauth_context = oauth_context_dict
                     logger.info(
                         "OAuth context shared with browser_app for session auth"
                     )
@@ -1194,29 +1398,87 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
                 f"OAuth context initialized for login routes (client_id={client_id[:16]}...)"
             )
         else:
-            # BasicAuth mode - share storage with browser_app for webhook management
+            # BasicAuth mode - initialize storage for webhook management
             from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 
-            storage = RefreshTokenStorage.from_env()
+            basic_auth_storage = RefreshTokenStorage.from_env()
-            await storage.initialize()
+            await basic_auth_storage.initialize()
+            logger.info("Initialized refresh token storage for webhook management")
 
-            app.state.storage = storage
+            app.state.storage = basic_auth_storage
+
+            # For multi-user BasicAuth with offline access, create oauth_context for management APIs
+            # This allows Astrolabe to use management APIs with OAuth bearer tokens
+            if settings.enable_multi_user_basic_auth and settings.enable_offline_access:
+                # Check if we have OAuth credentials from DCR
+                if multi_user_basic_oauth_creds:
+                    sync_client_id, sync_client_secret = multi_user_basic_oauth_creds
+
+                    # Create minimal oauth_context for management API authentication
+                    nextcloud_host_for_context = settings.nextcloud_host
+                    mcp_server_url = os.getenv(
+                        "NEXTCLOUD_MCP_SERVER_URL", "http://localhost:8000"
+                    )
+                    discovery_url = os.getenv(
+                        "OIDC_DISCOVERY_URL",
+                        f"{nextcloud_host_for_context}/.well-known/openid-configuration",
+                    )
+
+                    oauth_context_dict = {
+                        "storage": basic_auth_storage,
+                        "oauth_client": None,  # Not needed for management APIs
+                        "token_verifier": None,  # Will be set when token broker is created
+                        "config": {
+                            "mcp_server_url": mcp_server_url,
+                            "discovery_url": discovery_url,
+                            "client_id": sync_client_id,
+                            "client_secret": sync_client_secret,
+                            "scopes": "",  # Background sync only
+                            "nextcloud_host": nextcloud_host_for_context,
+                            "nextcloud_resource_uri": nextcloud_host_for_context,
+                            "oauth_provider": "nextcloud",  # Always Nextcloud for multi-user BasicAuth
+                        },
+                    }
+                    app.state.oauth_context = oauth_context_dict
+                    logger.info(
+                        f"OAuth context initialized for management APIs (multi-user BasicAuth, client_id={sync_client_id[:16]}...)"
+                    )
 
             # Also share with browser_app for webhook routes
             for route in app.routes:
                 if isinstance(route, Mount) and route.path == "/app":
-                    route.app.state.storage = storage
+                    browser_app = cast(Starlette, route.app)
+                    browser_app.state.storage = basic_auth_storage
+                    if (
+                        settings.enable_multi_user_basic_auth
+                        and settings.enable_offline_access
+                        and hasattr(app.state, "oauth_context")
+                    ):
+                        browser_app.state.oauth_context = app.state.oauth_context
+                        logger.info(
+                            "OAuth context shared with browser_app for management APIs"
+                        )
                     logger.info(
                         "Storage shared with browser_app for webhook management"
                     )
                     break
 
-        # Start background vector sync tasks for BasicAuth mode (ADR-007)
+        # Start background vector sync tasks (ADR-007)
         # Scanner runs at server-level (once), not per-session
         import anyio as anyio_module
 
-        settings = get_settings()
+        # Re-use settings from outer scope (already validated)
-        if not oauth_enabled and settings.vector_sync_enabled:
+        # Note: enable_offline_access_for_sync, encryption_key, and refresh_token_storage
+        # are already defined in outer scope before mode split
+
+        # Multi-user BasicAuth uses OAuth-style background sync (with app passwords)
+        # So skip single-user BasicAuth vector sync if in multi-user mode
+        if (
+            settings.vector_sync_enabled
+            and not oauth_enabled
+            and not settings.enable_multi_user_basic_auth
+        ):
+            # BasicAuth mode - single user sync
             logger.info("Starting background vector sync tasks for BasicAuth mode")
 
             # Get username from environment
@@ -1265,10 +1527,11 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
             # Also share with browser_app for /app route
             for route in app.routes:
                 if isinstance(route, Mount) and route.path == "/app":
-                    route.app.state.document_send_stream = send_stream
+                    browser_app = cast(Starlette, route.app)
-                    route.app.state.document_receive_stream = receive_stream
+                    browser_app.state.document_send_stream = send_stream
-                    route.app.state.shutdown_event = shutdown_event
+                    browser_app.state.document_receive_stream = receive_stream
-                    route.app.state.scanner_wake_event = scanner_wake_event
+                    browser_app.state.shutdown_event = shutdown_event
+                    browser_app.state.scanner_wake_event = scanner_wake_event
                     logger.info("Vector sync state shared with browser_app for /app")
                     break
 
@@ -1311,8 +1574,207 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
                         shutdown_event.set()
                         await client.close()
                         # TaskGroup automatically cancels all tasks on exit
+
+        elif (
+            settings.vector_sync_enabled
+            and (oauth_enabled or settings.enable_multi_user_basic_auth)
+            and settings.enable_offline_access
+        ):
+            # OAuth mode with offline access - multi-user sync
+            # Also used for multi-user BasicAuth mode (client auth is BasicAuth, background sync uses app passwords)
+            mode_desc = "OAuth mode" if oauth_enabled else "Multi-user BasicAuth mode"
+            logger.info(f"Starting background vector sync tasks for {mode_desc}")
+
+            from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
+            from nextcloud_mcp_server.vector.oauth_sync import (
+                oauth_processor_task,
+                user_manager_task,
+            )
+
+            # Get nextcloud_host (from settings - already validated)
+            nextcloud_host_for_sync = settings.nextcloud_host
+            if not nextcloud_host_for_sync:
+                raise ValueError("NEXTCLOUD_HOST required for vector sync")
+
+            # Get OIDC discovery URL (same as used for OAuth setup)
+            discovery_url = os.getenv(
+                "OIDC_DISCOVERY_URL",
+                f"{nextcloud_host_for_sync}/.well-known/openid-configuration",
+            )
+
+            # Get client credentials - these were obtained before uvicorn started
+            # For OAuth modes: from setup_oauth_config()
+            # For multi-user BasicAuth: from setup_multi_user_basic_dcr()
+            oauth_ctx = getattr(app.state, "oauth_context", {})
+            oauth_config = oauth_ctx.get("config", {})
+            sync_client_id = oauth_config.get("client_id")
+            sync_client_secret = oauth_config.get("client_secret")
+
+            # For multi-user BasicAuth mode, use pre-obtained credentials from outer scope
+            if not sync_client_id or not sync_client_secret:
+                if multi_user_basic_oauth_creds:
+                    sync_client_id, sync_client_secret = multi_user_basic_oauth_creds
+                    logger.info(
+                        "Using pre-obtained OAuth credentials for background sync"
+                    )
+                else:
+                    # No credentials available - DCR was attempted before uvicorn started but failed
+                    sync_client_id = None
+                    sync_client_secret = None
+                    logger.warning(
+                        "OAuth credentials not available for background sync "
+                        "(DCR was attempted during startup but failed)"
+                    )
+
+            # Only start vector sync if credentials are available
+            if sync_client_id and sync_client_secret:
+                # Get storage - different for OAuth vs multi-user BasicAuth modes
+                # OAuth mode: refresh_token_storage (from setup_oauth_config)
+                # Multi-user BasicAuth: app.state.storage (basic_auth_storage)
+                token_storage = (
+                    refresh_token_storage if oauth_enabled else app.state.storage
+                )
+
+                # Create token broker for background operations
+                # Note: storage handles encryption internally, no key needed here
+                # Client credentials are needed for token refresh operations
+                token_broker = TokenBrokerService(
+                    storage=token_storage,
+                    oidc_discovery_url=discovery_url,
+                    nextcloud_host=nextcloud_host_for_sync,
+                    client_id=sync_client_id,
+                    client_secret=sync_client_secret,
+                )
+
+                # Store token broker in oauth_context for management API (revoke endpoint)
+                if hasattr(app.state, "oauth_context"):
+                    app.state.oauth_context["token_broker"] = token_broker
+                    logger.info(
+                        "Token broker added to oauth_context for management API"
+                    )
+
+                # Initialize Qdrant collection before starting background tasks
+                logger.info("Initializing Qdrant collection...")
+                from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
+
+                try:
+                    await get_qdrant_client()  # Triggers collection creation if needed
+                    logger.info("Qdrant collection ready")
+                except Exception as e:
+                    logger.error(f"Failed to initialize Qdrant collection: {e}")
+                    raise RuntimeError(
+                        f"Cannot start vector sync - Qdrant initialization failed: {e}"
+                    ) from e
+
+                # Initialize shared state
+                send_stream, receive_stream = anyio_module.create_memory_object_stream(
+                    max_buffer_size=settings.vector_sync_queue_max_size
+                )
+                shutdown_event = anyio_module.Event()
+                scanner_wake_event = anyio_module.Event()
+
+                # User state tracking for user manager
+                user_states: dict = {}
+
+                # Store in app state for access from routes (ADR-007)
+                app.state.document_send_stream = send_stream
+                app.state.document_receive_stream = receive_stream
+                app.state.shutdown_event = shutdown_event
+                app.state.scanner_wake_event = scanner_wake_event
+
+                # Also store in module singleton for FastMCP session lifespans
+                _vector_sync_state.document_send_stream = send_stream
+                _vector_sync_state.document_receive_stream = receive_stream
+                _vector_sync_state.shutdown_event = shutdown_event
+                _vector_sync_state.scanner_wake_event = scanner_wake_event
+                logger.info("Vector sync state stored in module singleton")
+
+                # Also share with browser_app for /app route
+                for route in app.routes:
+                    if isinstance(route, Mount) and route.path == "/app":
+                        browser_app = cast(Starlette, route.app)
+                        browser_app.state.document_send_stream = send_stream
+                        browser_app.state.document_receive_stream = receive_stream
+                        browser_app.state.shutdown_event = shutdown_event
+                        browser_app.state.scanner_wake_event = scanner_wake_event
+                        logger.info(
+                            "Vector sync state shared with browser_app for /app"
+                        )
+                        break
+
+                # Start background tasks using anyio TaskGroup
+                async with anyio_module.create_task_group() as tg:
+                    # Start user manager task (supervises per-user scanners)
+                    await tg.start(
+                        user_manager_task,
+                        send_stream,
+                        shutdown_event,
+                        scanner_wake_event,
+                        token_broker,
+                        token_storage,  # Use token_storage (works for both OAuth and multi-user BasicAuth)
+                        nextcloud_host_for_sync,
+                        user_states,
+                        tg,
+                    )
+
+                    # Start processor pool (each gets a cloned receive stream)
+                    for i in range(settings.vector_sync_processor_workers):
+                        await tg.start(
+                            oauth_processor_task,
+                            i,
+                            receive_stream.clone(),
+                            shutdown_event,
+                            token_broker,
+                            nextcloud_host_for_sync,
+                        )
+
+                    logger.info(
+                        f"Background sync tasks started: 1 user manager + "
+                        f"{settings.vector_sync_processor_workers} processors"
+                    )
+
+                    # Run MCP session manager and yield
+                    async with AsyncExitStack() as stack:
+                        await stack.enter_async_context(mcp.session_manager.run())
+                        try:
+                            yield
+                        finally:
+                            # Shutdown signal
+                            logger.info("Shutting down background sync tasks")
+                            shutdown_event.set()
+                            # Close token broker HTTP client
+                            if token_broker._http_client:
+                                await token_broker._http_client.aclose()
+                            # TaskGroup automatically cancels all tasks on exit
+            else:
+                # No OAuth credentials available for background sync
+                logger.warning(
+                    "Skipping background vector sync - OAuth credentials not available. "
+                    "Multi-user BasicAuth mode will run without semantic search background operations. "
+                    "To enable, set NEXTCLOUD_OIDC_CLIENT_ID and NEXTCLOUD_OIDC_CLIENT_SECRET."
+                )
+                # Just run MCP session manager without vector sync
+                async with AsyncExitStack() as stack:
+                    await stack.enter_async_context(mcp.session_manager.run())
+                    yield
+
         else:
             # No vector sync - just run MCP session manager
+            if settings.vector_sync_enabled:
+                # Log why vector sync is not starting
+                if oauth_enabled and not settings.enable_offline_access:
+                    logger.warning(
+                        "Vector sync enabled but ENABLE_OFFLINE_ACCESS=false - "
+                        "vector sync requires offline access in OAuth mode"
+                    )
+                elif oauth_enabled and not refresh_token_storage:
+                    logger.warning(
+                        "Vector sync enabled but refresh token storage not available"
+                    )
+                elif oauth_enabled and not os.getenv("TOKEN_ENCRYPTION_KEY"):
+                    logger.warning(
+                        "Vector sync enabled but TOKEN_ENCRYPTION_KEY not set"
+                    )
             async with AsyncExitStack() as stack:
                 await stack.enter_async_context(mcp.session_manager.run())
                 yield
@@ -1372,12 +1834,20 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
             is_ready = False
 
         # Check authentication configuration
-        if oauth_enabled:
+        # Report the deployment mode, not just whether OAuth is enabled
-            # OAuth mode - just verify we got this far (token_verifier initialized in lifespan)
+        # This helps clients (like Astrolabe) determine which auth flow to use
+        if (
+            mode == AuthMode.OAUTH_SINGLE_AUDIENCE
+            or mode == AuthMode.OAUTH_TOKEN_EXCHANGE
+        ):
             checks["auth_mode"] = "oauth"
             checks["auth_configured"] = "ok"
-        else:
+        elif mode == AuthMode.MULTI_USER_BASIC:
-            # BasicAuth mode - verify credentials are set
+            checks["auth_mode"] = "multi_user_basic"
+            checks["auth_configured"] = "ok"
+            # Indicate if app passwords are supported (when offline_access enabled)
+            checks["supports_app_passwords"] = settings.enable_offline_access
+        elif mode == AuthMode.SINGLE_USER_BASIC:
             username = os.getenv("NEXTCLOUD_USERNAME")
             password = os.getenv("NEXTCLOUD_PASSWORD")
             if username and password:
@@ -1387,6 +1857,9 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
                 checks["auth_mode"] = "basic"
                 checks["auth_configured"] = "error: credentials not set"
                 is_ready = False
+        elif mode == AuthMode.SMITHERY_STATELESS:
+            checks["auth_mode"] = "smithery"
+            checks["auth_configured"] = "ok"
 
         # Check Qdrant status if using network mode (external Qdrant service)
         # In-memory and persistent modes use embedded Qdrant, no external service to check
@@ -1468,6 +1941,70 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
     )
     logger.info("Test webhook endpoint enabled: /webhooks/nextcloud")
 
+    # Add management API endpoints for Nextcloud PHP app
+    # Available in: OAuth modes OR multi-user BasicAuth with offline access (for Astrolabe integration)
+    enable_management_apis = oauth_enabled or (
+        settings.enable_multi_user_basic_auth and settings.enable_offline_access
+    )
+    if enable_management_apis:
+        from nextcloud_mcp_server.api.management import (
+            create_webhook,
+            delete_webhook,
+            get_chunk_context,
+            get_installed_apps,
+            get_server_status,
+            get_user_session,
+            get_vector_sync_status,
+            list_webhooks,
+            revoke_user_access,
+            unified_search,
+            vector_search,
+        )
+
+        routes.append(Route("/api/v1/status", get_server_status, methods=["GET"]))
+        routes.append(
+            Route(
+                "/api/v1/vector-sync/status",
+                get_vector_sync_status,
+                methods=["GET"],
+            )
+        )
+        routes.append(
+            Route(
+                "/api/v1/users/{user_id}/session",
+                get_user_session,
+                methods=["GET"],
+            )
+        )
+        routes.append(
+            Route(
+                "/api/v1/users/{user_id}/revoke",
+                revoke_user_access,
+                methods=["POST"],
+            )
+        )
+        routes.append(
+            Route("/api/v1/vector-viz/search", vector_search, methods=["POST"])
+        )
+        routes.append(
+            Route("/api/v1/chunk-context", get_chunk_context, methods=["GET"])
+        )
+        # ADR-018: Unified search endpoint for Nextcloud PHP app integration
+        routes.append(Route("/api/v1/search", unified_search, methods=["POST"]))
+        routes.append(Route("/api/v1/apps", get_installed_apps, methods=["GET"]))
+        # Webhook management endpoints
+        routes.append(Route("/api/v1/webhooks", list_webhooks, methods=["GET"]))
+        routes.append(Route("/api/v1/webhooks", create_webhook, methods=["POST"]))
+        routes.append(
+            Route("/api/v1/webhooks/{webhook_id}", delete_webhook, methods=["DELETE"])
+        )
+        logger.info(
+            "Management API endpoints enabled: /api/v1/status, /api/v1/vector-sync/status, "
+            "/api/v1/users/{user_id}/session, /api/v1/users/{user_id}/revoke, "
+            "/api/v1/vector-viz/search, /api/v1/search, /api/v1/apps, "
+            "/api/v1/webhooks"
+        )
+
     # ADR-016: Add Smithery well-known config endpoint for container runtime discovery
     if deployment_mode == DeploymentMode.SMITHERY_STATELESS:
 
@@ -1836,4 +2373,11 @@ def get_app(transport: str = "streamable-http", enabled_apps: list[str] | None =
         app = SmitheryConfigMiddleware(app)
         logger.info("SmitheryConfigMiddleware enabled for query parameter config")
 
+    # Apply BasicAuthMiddleware for multi-user BasicAuth pass-through mode
+    if settings.enable_multi_user_basic_auth:
+        app = BasicAuthMiddleware(app)
+        logger.info(
+            "BasicAuthMiddleware enabled - multi-user BasicAuth pass-through mode active"
+        )
+
     return app

nextcloud_mcp_server/auth/astrolabe_client.py

@@ -0,0 +1,152 @@
+"""
+Client for querying Astrolabe Management API for background sync credentials.
+
+This client uses OAuth client credentials flow to authenticate to Nextcloud
+and retrieve user app passwords for background sync operations.
+"""
+
+import logging
+import time
+from typing import Optional
+
+import httpx
+
+logger = logging.getLogger(__name__)
+
+
+class AstrolabeClient:
+    """Client for querying Astrolabe API for background sync credentials.
+
+    Uses OAuth client credentials flow to authenticate as the MCP server
+    and retrieve user app passwords that are stored in Nextcloud.
+    """
+
+    def __init__(
+        self,
+        nextcloud_host: str,
+        client_id: str,
+        client_secret: str,
+    ):
+        """
+        Initialize Astrolabe client.
+
+        Args:
+            nextcloud_host: Nextcloud base URL (e.g., https://cloud.example.com)
+            client_id: OAuth client ID for MCP server
+            client_secret: OAuth client secret
+        """
+        self.nextcloud_host = nextcloud_host.rstrip("/")
+        self.client_id = client_id
+        self.client_secret = client_secret
+        self._token_cache: Optional[dict] = None  # {access_token, expires_at}
+
+    async def get_access_token(self) -> str:
+        """
+        Get access token using OAuth client credentials flow.
+
+        Tokens are cached with 1-minute early refresh to avoid expiration.
+
+        Returns:
+            Access token string
+
+        Raises:
+            httpx.HTTPError: If token request fails
+        """
+        # Check cache
+        if self._token_cache and time.time() < self._token_cache["expires_at"]:
+            logger.debug("Using cached OAuth token for Astrolabe API")
+            return self._token_cache["access_token"]
+
+        # Discover token endpoint
+        discovery_url = f"{self.nextcloud_host}/.well-known/openid-configuration"
+
+        async with httpx.AsyncClient() as client:
+            logger.debug(f"Discovering token endpoint from {discovery_url}")
+            discovery_resp = await client.get(discovery_url)
+            discovery_resp.raise_for_status()
+            token_endpoint = discovery_resp.json()["token_endpoint"]
+
+            logger.debug(f"Requesting client credentials token from {token_endpoint}")
+
+            # Request token using client credentials grant
+            token_resp = await client.post(
+                token_endpoint,
+                data={
+                    "grant_type": "client_credentials",
+                    "client_id": self.client_id,
+                    "client_secret": self.client_secret,
+                    "scope": "openid",  # Minimal scope
+                },
+            )
+            token_resp.raise_for_status()
+            data = token_resp.json()
+
+            # Cache with 1-minute early refresh
+            expires_in = data.get("expires_in", 3600)
+            self._token_cache = {
+                "access_token": data["access_token"],
+                "expires_at": time.time() + expires_in - 60,
+            }
+
+            logger.info(f"Obtained Astrolabe API token (expires in {expires_in}s)")
+            return data["access_token"]
+
+    async def get_user_app_password(self, user_id: str) -> Optional[str]:
+        """
+        Retrieve user's app password for background sync.
+
+        Args:
+            user_id: Nextcloud user ID
+
+        Returns:
+            App password string, or None if user hasn't provisioned
+
+        Raises:
+            httpx.HTTPError: If API request fails (except 404)
+        """
+        token = await self.get_access_token()
+        url = f"{self.nextcloud_host}/apps/astrolabe/api/v1/background-sync/credentials/{user_id}"
+
+        async with httpx.AsyncClient() as client:
+            logger.debug(f"Retrieving app password for user: {user_id}")
+
+            response = await client.get(
+                url,
+                headers={"Authorization": f"Bearer {token}"},
+                timeout=10.0,
+            )
+
+            if response.status_code == 404:
+                logger.debug(f"No app password configured for user: {user_id}")
+                return None
+
+            response.raise_for_status()
+            data = response.json()
+
+            logger.info(
+                f"Retrieved app password for user: {user_id} (type: {data.get('credential_type')})"
+            )
+            return data.get("app_password")
+
+    async def get_background_sync_status(self, user_id: str) -> dict:
+        """
+        Get background sync status for a user.
+
+        Args:
+            user_id: Nextcloud user ID
+
+        Returns:
+            Dict with keys: has_access, credential_type, provisioned_at
+
+        Raises:
+            httpx.HTTPError: If API request fails
+        """
+        # For now, check if app password exists
+        # In the future, this could query a dedicated status endpoint
+        app_password = await self.get_user_app_password(user_id)
+
+        return {
+            "has_access": app_password is not None,
+            "credential_type": "app_password" if app_password else None,
+            "provisioned_at": None,  # TODO: Get from API if available
+        }

nextcloud_mcp_server/auth/browser_oauth_routes.py

@@ -24,6 +24,26 @@ from nextcloud_mcp_server.auth.userinfo_routes import (
 logger = logging.getLogger(__name__)
 
 
+def _should_use_secure_cookies() -> bool:
+    """Determine if cookies should have secure flag.
+
+    Checks COOKIE_SECURE env var first, then auto-detects from NEXTCLOUD_HOST.
+
+    Returns:
+        True if cookies should be secure (HTTPS), False otherwise
+    """
+    # Explicit configuration takes precedence
+    explicit = os.getenv("COOKIE_SECURE", "").lower()
+    if explicit == "true":
+        return True
+    if explicit == "false":
+        return False
+
+    # Auto-detect from NEXTCLOUD_HOST protocol
+    nextcloud_host = os.getenv("NEXTCLOUD_HOST", "")
+    return nextcloud_host.startswith("https://")
+
+
 async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
     """Browser OAuth login endpoint - redirects to IdP for authentication.
 
@@ -50,6 +70,10 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
     logger.info(f"oauth_login called - client_id: {oauth_config.get('client_id')}")
     logger.info(f"oauth_login called - oauth_client: {oauth_client is not None}")
 
+    # Get redirect URL from query params (default to /app)
+    next_url = request.query_params.get("next", "/app")
+    logger.info(f"oauth_login - next_url: {next_url}")
+
     # Generate state for CSRF protection
     state = secrets.token_urlsafe(32)
 
@@ -71,7 +95,7 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
     await storage.store_oauth_session(
         session_id=state,  # Use state as session ID
         client_id="browser-ui",
-        client_redirect_uri="/app",
+        client_redirect_uri=next_url,  # Store the redirect URL for after auth
         state=state,
         code_challenge=code_challenge,
         code_challenge_method="S256",
@@ -85,6 +109,11 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
         if not oauth_client.authorization_endpoint:
             await oauth_client.discover()
 
+        # Get Nextcloud resource URI for audience (background sync needs Nextcloud-scoped tokens)
+        nextcloud_resource_uri = oauth_config.get(
+            "nextcloud_resource_uri", oauth_config.get("nextcloud_host")
+        )
+
         idp_params = {
             "client_id": oauth_client.client_id,
             "redirect_uri": callback_uri,
@@ -94,6 +123,7 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
             "code_challenge": code_challenge,
             "code_challenge_method": "S256",
             "prompt": "consent",  # Ensure refresh token
+            "resource": nextcloud_resource_uri,  # Request tokens for Nextcloud API access
         }
 
         auth_url = f"{oauth_client.authorization_endpoint}?{urlencode(idp_params)}"
@@ -131,6 +161,11 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
                     f"{public_parsed.scheme}://{public_parsed.netloc}{auth_parsed.path}"
                 )
 
+        # Get Nextcloud resource URI for audience (background sync needs Nextcloud-scoped tokens)
+        nextcloud_resource_uri = oauth_config.get(
+            "nextcloud_resource_uri", oauth_config.get("nextcloud_host")
+        )
+
         idp_params = {
             "client_id": oauth_config["client_id"],
             "redirect_uri": callback_uri,
@@ -140,6 +175,7 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
             "code_challenge": code_challenge,
             "code_challenge_method": "S256",
             "prompt": "consent",  # Ensure refresh token
+            "resource": nextcloud_resource_uri,  # Request tokens for Nextcloud API access
         }
 
         # Debug: Log full parameters
@@ -214,12 +250,15 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
     oauth_client = oauth_ctx["oauth_client"]
     oauth_config = oauth_ctx["config"]
 
-    # Retrieve code_verifier from session storage (PKCE required for all modes)
+    # Retrieve code_verifier and redirect URL from session storage
     code_verifier = ""
+    next_url = "/app"  # Default redirect
     oauth_session = await storage.get_oauth_session(state)
     if oauth_session:
         # code_verifier was stored in mcp_authorization_code field
         code_verifier = oauth_session.get("mcp_authorization_code", "")
+        # next_url was stored in client_redirect_uri field
+        next_url = oauth_session.get("client_redirect_uri", "/app")
         # Clean up the temporary session
         # Note: We don't have delete_oauth_session method, but it will expire after TTL
 
@@ -262,6 +301,25 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
                 discovery = response.json()
                 token_endpoint = discovery["token_endpoint"]
 
+            # Rewrite token_endpoint from public URL to internal Docker URL
+            # Discovery document returns public URLs (e.g., http://localhost:8080/...)
+            # but server-side requests must use internal Docker network (e.g., http://app:80/...)
+            public_issuer = os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL")
+            if public_issuer:
+                from urllib.parse import urlparse as parse_url
+
+                internal_host = oauth_config["nextcloud_host"]
+                internal_parsed = parse_url(internal_host)
+                token_parsed = parse_url(token_endpoint)
+                public_parsed = parse_url(public_issuer)
+
+                if token_parsed.hostname == public_parsed.hostname:
+                    # Replace public URL with internal Docker URL
+                    token_endpoint = f"{internal_parsed.scheme}://{internal_parsed.netloc}{token_parsed.path}"
+                    logger.info(
+                        f"Rewrote token endpoint to internal URL: {token_endpoint}"
+                    )
+
             token_params = {
                 "grant_type": "authorization_code",
                 "code": code,
@@ -338,16 +396,35 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
         user_id = f"user-{secrets.token_hex(8)}"
         username = "unknown"
 
+    # Calculate refresh token expiration from token response
+    refresh_expires_in = token_data.get("refresh_expires_in")
+    refresh_expires_at = None
+    if refresh_expires_in:
+        import time
+
+        refresh_expires_at = int(time.time()) + refresh_expires_in
+        logger.info(
+            f"Refresh token expires in {refresh_expires_in}s (at timestamp {refresh_expires_at})"
+        )
+
+    # Extract granted scopes
+    granted_scopes = (
+        token_data.get("scope", "").split() if token_data.get("scope") else None
+    )
+
     # Store refresh token (for background jobs ONLY)
     if refresh_token:
         logger.info(f"Storing refresh token for user_id: {user_id}")
         logger.info(f"  State parameter (provisioning_client_id): {state[:16]}...")
+        logger.info(f"  Granted scopes: {granted_scopes}")
+        logger.info(f"  Expires at: {refresh_expires_at}")
         await storage.store_refresh_token(
             user_id=user_id,
             refresh_token=refresh_token,
-            expires_at=None,
+            expires_at=refresh_expires_at,
             flow_type="browser",  # Browser-based login flow
             provisioning_client_id=state,  # Store state for unified session lookup
+            scopes=granted_scopes,
         )
         logger.info(f"✓ Refresh token stored successfully for user_id: {user_id}")
         logger.info(
@@ -383,13 +460,14 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
             # Continue anyway - profile cache is optional for browser UI
 
     # Create response and set session cookie
-    response = RedirectResponse("/app", status_code=302)
+    # Redirect to stored next_url (from OAuth session) or /app as default
+    response = RedirectResponse(next_url, status_code=302)
     response.set_cookie(
         key="mcp_session",
         value=user_id,
         max_age=86400 * 30,  # 30 days
         httponly=True,
-        secure=False,  # Set to True in production with HTTPS
+        secure=_should_use_secure_cookies(),
         samesite="lax",
     )
 

nextcloud_mcp_server/auth/oauth_routes.py

@@ -517,12 +517,23 @@ async def oauth_callback_nextcloud(request: Request):
             token_data.get("scope", "").split() if token_data.get("scope") else None
         )
 
+        # Calculate refresh token expiration from token response
+        refresh_expires_in = token_data.get("refresh_expires_in")
+        refresh_expires_at = None
+        if refresh_expires_in:
+            import time
+
+            refresh_expires_at = int(time.time()) + refresh_expires_in
+            logger.info(f"  refresh_expires_in: {refresh_expires_in}s")
+            logger.info(f"  refresh_expires_at: {refresh_expires_at}")
+
         logger.info("Storing refresh token:")
         logger.info(f"  user_id: {user_id}")
         logger.info("  flow_type: flow2")
         logger.info("  token_audience: nextcloud")
         logger.info(f"  provisioning_client_id: {state[:16]}...")
         logger.info(f"  scopes: {granted_scopes}")
+        logger.info(f"  expires_at: {refresh_expires_at}")
 
         await storage.store_refresh_token(
             user_id=user_id,
@@ -531,7 +542,7 @@ async def oauth_callback_nextcloud(request: Request):
             token_audience="nextcloud",
             provisioning_client_id=state,  # Store which client initiated provisioning
             scopes=granted_scopes,
-            expires_at=None,  # Refresh tokens typically don't expire
+            expires_at=refresh_expires_at,
         )
         logger.info(f"✓ Stored Flow 2 master refresh token for user {user_id}")
         logger.info("=" * 60)

nextcloud_mcp_server/auth/static/vector-viz.js

@@ -201,8 +201,15 @@ function vizApp() {
                     return `${baseUrl}/apps/calendar`;
                 case 'contact':
                     return `${baseUrl}/apps/contacts`;
-                case 'deck':
+                case 'deck_card':
+                    // URL pattern: /apps/deck/board/:boardId/card/:cardId
+                    if (result.metadata && result.metadata.board_id) {
+                        return `${baseUrl}/apps/deck/board/${result.metadata.board_id}/card/${result.id}`;
+                    }
+                    // Fallback if board_id not available
                     return `${baseUrl}/apps/deck`;
+                case 'news_item':
+                    return `${baseUrl}/apps/news/item/${result.id}`;
                 default:
                     return `${baseUrl}`;
             }

nextcloud_mcp_server/auth/storage.py

@@ -117,7 +117,14 @@ class RefreshTokenStorage:
         return cls(db_path=db_path, encryption_key=encryption_key)
 
     async def initialize(self) -> None:
-        """Initialize database schema"""
+        """
+        Initialize database schema using Alembic migrations.
+
+        This method handles three scenarios:
+        1. New database: Run migrations from scratch
+        2. Pre-Alembic database: Stamp with initial revision (no changes)
+        3. Alembic-managed database: Upgrade to latest version
+        """
         if self._initialized:
             return
 
@@ -125,137 +132,59 @@ class RefreshTokenStorage:
         db_dir = Path(self.db_path).parent
         db_dir.mkdir(parents=True, exist_ok=True)
 
-        # Set restrictive permissions on database file
+        # Set restrictive permissions on database file if it exists
         if Path(self.db_path).exists():
             os.chmod(self.db_path, 0o600)
 
+        # Check database state and run appropriate migration strategy
         async with aiosqlite.connect(self.db_path) as db:
-            await db.execute(
+            # Check if database is managed by Alembic
-                """
+            cursor = await db.execute(
-                CREATE TABLE IF NOT EXISTS refresh_tokens (
+                "SELECT name FROM sqlite_master WHERE type='table' AND name='alembic_version'"
-                    user_id TEXT PRIMARY KEY,
+            )
-                    encrypted_token BLOB NOT NULL,
+            has_alembic = await cursor.fetchone() is not None
-                    expires_at INTEGER,
+
-                    created_at INTEGER NOT NULL,
+            if not has_alembic:
-                    updated_at INTEGER NOT NULL,
+                # Check if this is a pre-Alembic database with existing schema
-                    -- ADR-004 Progressive Consent fields
+                cursor = await db.execute(
-                    flow_type TEXT DEFAULT 'hybrid',  -- 'hybrid', 'flow1', 'flow2'
+                    "SELECT name FROM sqlite_master WHERE type='table' AND name='refresh_tokens'"
-                    token_audience TEXT DEFAULT 'nextcloud',  -- 'mcp-server' or 'nextcloud'
-                    provisioned_at INTEGER,  -- When Flow 2 was completed
-                    provisioning_client_id TEXT,  -- Which MCP client initiated Flow 1
-                    scopes TEXT,  -- JSON array of granted scopes
-                    -- Browser session profile cache
-                    user_profile TEXT,  -- JSON cache of IdP user profile (for browser UI only)
-                    profile_cached_at INTEGER  -- When profile was last cached
                 )
-                """
+                has_schema = await cursor.fetchone() is not None
-            )
 
-            await db.execute(
+                if has_schema:
-                """
+                    logger.info(
-                CREATE TABLE IF NOT EXISTS audit_logs (
+                        f"Detected pre-Alembic database at {self.db_path}, "
-                    id INTEGER PRIMARY KEY AUTOINCREMENT,
+                        "stamping with initial revision"
-                    timestamp INTEGER NOT NULL,
+                    )
-                    event TEXT NOT NULL,
+                else:
-                    user_id TEXT NOT NULL,
+                    logger.info(
-                    resource_type TEXT,
+                        f"Initializing new database at {self.db_path} with migrations"
-                    resource_id TEXT,
+                    )
-                    auth_method TEXT,
+
-                    hostname TEXT
+        # Run migrations in a worker thread using anyio.to_thread
+        # This allows Alembic to run its own async operations in a separate context
+        from anyio import to_thread
+
+        from nextcloud_mcp_server.migrations import stamp_database, upgrade_database
+
+        if not has_alembic:
+            if has_schema:
+                # Stamp existing database without running migrations
+                await to_thread.run_sync(stamp_database, self.db_path, "001")
+                logger.info(
+                    "Pre-Alembic database stamped successfully. "
+                    "Future schema changes will use migrations."
                 )
-                """
+            else:
-            )
+                # New database - run migrations
+                await to_thread.run_sync(upgrade_database, self.db_path, "head")
+                logger.info("Database initialized with migrations")
+        else:
+            # Alembic-managed database - upgrade to latest
+            await to_thread.run_sync(upgrade_database, self.db_path, "head")
+            logger.info("Database upgraded to latest version")
 
-            # Create index on audit logs for efficient queries
+        # Set restrictive permissions after initialization
-            await db.execute(
-                "CREATE INDEX IF NOT EXISTS idx_audit_user_timestamp "
-                "ON audit_logs(user_id, timestamp)"
-            )
-
-            # OAuth client credentials storage
-            await db.execute(
-                """
-                CREATE TABLE IF NOT EXISTS oauth_clients (
-                    id INTEGER PRIMARY KEY,
-                    client_id TEXT UNIQUE NOT NULL,
-                    encrypted_client_secret BLOB NOT NULL,
-                    client_id_issued_at INTEGER NOT NULL,
-                    client_secret_expires_at INTEGER NOT NULL,
-                    redirect_uris TEXT NOT NULL,
-                    encrypted_registration_access_token BLOB,
-                    registration_client_uri TEXT,
-                    created_at INTEGER NOT NULL,
-                    updated_at INTEGER NOT NULL
-                )
-                """
-            )
-
-            # OAuth flow sessions (ADR-004 Progressive Consent)
-            await db.execute(
-                """
-                CREATE TABLE IF NOT EXISTS oauth_sessions (
-                    session_id TEXT PRIMARY KEY,
-                    client_id TEXT,
-                    client_redirect_uri TEXT NOT NULL,
-                    state TEXT,
-                    code_challenge TEXT,
-                    code_challenge_method TEXT,
-                    mcp_authorization_code TEXT UNIQUE,
-                    idp_access_token TEXT,
-                    idp_refresh_token TEXT,
-                    user_id TEXT,
-                    created_at INTEGER NOT NULL,
-                    expires_at INTEGER NOT NULL,
-                    -- ADR-004 Progressive Consent fields
-                    flow_type TEXT DEFAULT 'hybrid',  -- 'hybrid', 'flow1', 'flow2'
-                    requested_scopes TEXT,  -- JSON array of requested scopes
-                    granted_scopes TEXT,  -- JSON array of granted scopes
-                    is_provisioning BOOLEAN DEFAULT FALSE  -- True if this is a Flow 2 provisioning session
-                )
-                """
-            )
-
-            # Create index for MCP authorization code lookups
-            await db.execute(
-                "CREATE INDEX IF NOT EXISTS idx_oauth_sessions_mcp_code "
-                "ON oauth_sessions(mcp_authorization_code)"
-            )
-
-            # Schema version tracking
-            await db.execute(
-                """
-                CREATE TABLE IF NOT EXISTS schema_version (
-                    version INTEGER PRIMARY KEY,
-                    applied_at REAL NOT NULL
-                )
-                """
-            )
-
-            # Registered webhooks tracking (both BasicAuth and OAuth modes)
-            await db.execute(
-                """
-                CREATE TABLE IF NOT EXISTS registered_webhooks (
-                    id INTEGER PRIMARY KEY AUTOINCREMENT,
-                    webhook_id INTEGER NOT NULL UNIQUE,
-                    preset_id TEXT NOT NULL,
-                    created_at REAL NOT NULL
-                )
-                """
-            )
-
-            # Create indexes for efficient webhook queries
-            await db.execute(
-                "CREATE INDEX IF NOT EXISTS idx_webhooks_preset "
-                "ON registered_webhooks(preset_id)"
-            )
-            await db.execute(
-                "CREATE INDEX IF NOT EXISTS idx_webhooks_created "
-                "ON registered_webhooks(created_at)"
-            )
-
-            await db.commit()
-
-        # Set restrictive permissions after creation
         os.chmod(self.db_path, 0o600)
 
         self._initialized = True
@@ -287,6 +216,8 @@ class RefreshTokenStorage:
         if not self._initialized:
             await self.initialize()
 
+        # Type narrowing: cipher is set after initialize()
+        assert self.cipher is not None
         encrypted_token = self.cipher.encrypt(refresh_token.encode())
         now = int(time.time())
         scopes_json = json.dumps(scopes) if scopes else None
@@ -432,6 +363,9 @@ class RefreshTokenStorage:
         if not self._initialized:
             await self.initialize()
 
+        # Type narrowing: cipher is set after initialize()
+        assert self.cipher is not None
+
         start_time = time.time()
         try:
             async with aiosqlite.connect(self.db_path) as db:
@@ -516,6 +450,9 @@ class RefreshTokenStorage:
         if not self._initialized:
             await self.initialize()
 
+        # Type narrowing: cipher is set after initialize()
+        assert self.cipher is not None
+
         async with aiosqlite.connect(self.db_path) as db:
             async with db.execute(
                 """
@@ -687,6 +624,9 @@ class RefreshTokenStorage:
         if not self._initialized:
             await self.initialize()
 
+        # Type narrowing: cipher is set after initialize()
+        assert self.cipher is not None
+
         # Encrypt sensitive data
         encrypted_secret = self.cipher.encrypt(client_secret.encode())
         encrypted_reg_token = (
@@ -757,6 +697,9 @@ class RefreshTokenStorage:
         if not self._initialized:
             await self.initialize()
 
+        # Type narrowing: cipher is set after initialize()
+        assert self.cipher is not None
+
         async with aiosqlite.connect(self.db_path) as db:
             async with db.execute(
                 """

nextcloud_mcp_server/auth/templates/vector_viz.html

@@ -65,8 +65,12 @@
                                     <span>Contacts</span>
                                 </label>
                                 <label style="display: flex; align-items: center; cursor: pointer; font-weight: normal;">
-                                    <input type="checkbox" x-model="docTypes" value="deck" style="margin-right: 4px;">
+                                    <input type="checkbox" x-model="docTypes" value="deck_card" style="margin-right: 4px;">
-                                    <span>Deck</span>
+                                    <span>Deck Cards</span>
+                                </label>
+                                <label style="display: flex; align-items: center; cursor: pointer; font-weight: normal;">
+                                    <input type="checkbox" x-model="docTypes" value="news_item" style="margin-right: 4px;">
+                                    <span>News</span>
                                 </label>
                             </div>
                         </div>

nextcloud_mcp_server/auth/token_broker.py

@@ -21,7 +21,6 @@ from typing import Dict, Optional, Tuple
 import anyio
 import httpx
 import jwt
-from cryptography.fernet import Fernet
 
 from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.auth.token_exchange import exchange_token_for_delegation
@@ -104,7 +103,8 @@ class TokenBrokerService:
         storage: RefreshTokenStorage,
         oidc_discovery_url: str,
         nextcloud_host: str,
-        encryption_key: str,
+        client_id: str,
+        client_secret: str,
         cache_ttl: int = 300,
         cache_early_refresh: int = 30,
     ):
@@ -112,23 +112,25 @@ class TokenBrokerService:
         Initialize the Token Broker Service.
 
         Args:
-            storage: Database storage for refresh tokens
+            storage: Database storage for refresh tokens (handles encryption internally)
             oidc_discovery_url: OIDC provider discovery URL
             nextcloud_host: Nextcloud server URL
-            encryption_key: Fernet key for token encryption
+            client_id: OAuth client ID for token operations
+            client_secret: OAuth client secret for token operations
             cache_ttl: Cache TTL in seconds (default: 5 minutes)
             cache_early_refresh: Early refresh threshold in seconds (default: 30 seconds)
         """
         self.storage = storage
         self.oidc_discovery_url = oidc_discovery_url
         self.nextcloud_host = nextcloud_host
-        self.fernet = Fernet(
+        self.client_id = client_id
-            encryption_key.encode()
+        self.client_secret = client_secret
-            if isinstance(encryption_key, str)
-            else encryption_key
-        )
         self.cache = TokenCache(cache_ttl, cache_early_refresh)
         self._oidc_config = None
+
+        # Per-user locks for token refresh operations (prevents race conditions)
+        self._user_refresh_locks: dict[str, anyio.Lock] = {}
+        self._locks_lock = anyio.Lock()  # Protects the locks dict itself
         self._http_client = None
 
     async def _get_http_client(self) -> httpx.AsyncClient:
@@ -139,6 +141,24 @@ class TokenBrokerService:
             )
         return self._http_client
 
+    async def _get_user_refresh_lock(self, user_id: str) -> anyio.Lock:
+        """
+        Get or create a lock for a specific user's refresh operations.
+
+        This prevents race conditions when multiple concurrent requests
+        attempt to refresh the same user's token simultaneously.
+
+        Args:
+            user_id: User ID to get lock for
+
+        Returns:
+            anyio.Lock for this user's refresh operations
+        """
+        async with self._locks_lock:
+            if user_id not in self._user_refresh_locks:
+                self._user_refresh_locks[user_id] = anyio.Lock()
+            return self._user_refresh_locks[user_id]
+
     async def _get_oidc_config(self) -> dict:
         """Get OIDC configuration from discovery endpoint."""
         if self._oidc_config is None:
@@ -148,6 +168,37 @@ class TokenBrokerService:
             self._oidc_config = response.json()
         return self._oidc_config
 
+    def _rewrite_token_endpoint(self, token_endpoint: str) -> str:
+        """Rewrite token endpoint from public URL to internal Docker URL.
+
+        OIDC discovery documents return public URLs (e.g., http://localhost:8080/...)
+        but server-side requests must use internal Docker network (e.g., http://app:80/...).
+
+        Args:
+            token_endpoint: Token endpoint URL from discovery document
+
+        Returns:
+            Rewritten URL using internal Docker host
+        """
+        import os
+        from urllib.parse import urlparse
+
+        public_issuer = os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL")
+        if not public_issuer:
+            return token_endpoint
+
+        internal_parsed = urlparse(self.nextcloud_host)
+        token_parsed = urlparse(token_endpoint)
+        public_parsed = urlparse(public_issuer)
+
+        if token_parsed.hostname == public_parsed.hostname:
+            # Replace public URL with internal Docker URL
+            rewritten = f"{internal_parsed.scheme}://{internal_parsed.netloc}{token_parsed.path}"
+            logger.info(f"Rewrote token endpoint: {token_endpoint} -> {rewritten}")
+            return rewritten
+
+        return token_endpoint
+
     async def get_nextcloud_token(self, user_id: str) -> Optional[str]:
         """
         Get a valid Nextcloud access token for the user.
@@ -180,9 +231,8 @@ class TokenBrokerService:
             return None
 
         try:
-            # Decrypt refresh token
+            # storage.get_refresh_token() returns already-decrypted token
-            encrypted_token = refresh_data["refresh_token"]
+            refresh_token = refresh_data["refresh_token"]
-            refresh_token = self.fernet.decrypt(encrypted_token.encode()).decode()
 
             # Exchange refresh token for new access token
             access_token, expires_in = await self._refresh_access_token(refresh_token)
@@ -271,41 +321,79 @@ class TokenBrokerService:
         """
         # Check cache first (background tokens can be cached)
         cache_key = f"{user_id}:background:{','.join(sorted(required_scopes))}"
+        refresh_in_progress_key = f"{user_id}:refresh_in_progress"
+
         cached_token = await self.cache.get(cache_key)
         if cached_token:
             return cached_token
 
-        # Get stored refresh token
+        # Acquire per-user lock BEFORE refresh operation to prevent race conditions
-        refresh_data = await self.storage.get_refresh_token(user_id)
+        refresh_lock = await self._get_user_refresh_lock(user_id)
-        if not refresh_data:
+        async with refresh_lock:
-            logger.info(f"No refresh token found for user {user_id}")
+            # Double-check cache after acquiring lock
-            return None
+            # (another thread may have refreshed while we waited)
+            cached_token = await self.cache.get(cache_key)
+            if cached_token:
+                logger.debug(
+                    f"Token found in cache after lock acquisition for user {user_id}"
+                )
+                return cached_token
 
-        try:
+            # Check if another thread is currently refreshing
-            # Decrypt refresh token
+            if await self.cache.get(refresh_in_progress_key):
-            encrypted_token = refresh_data["refresh_token"]
+                logger.debug(f"Refresh in progress for user {user_id}, waiting briefly")
-            refresh_token = self.fernet.decrypt(encrypted_token.encode()).decode()
+                await anyio.sleep(0.1)  # Brief wait for in-progress refresh
+                # Check cache one more time after wait
+                cached_token = await self.cache.get(cache_key)
+                if cached_token:
+                    logger.debug(
+                        f"Token refreshed by another thread for user {user_id}"
+                    )
+                    return cached_token
 
-            # Get token with specific scopes for background operation
+            # Mark refresh as in-progress
-            access_token, expires_in = await self._refresh_access_token_with_scopes(
+            await self.cache.set(refresh_in_progress_key, "true", expires_in=5)
-                refresh_token, required_scopes
-            )
 
-            # Cache the background token
+            try:
-            await self.cache.set(cache_key, access_token, expires_in)
+                # Get stored refresh token
+                refresh_data = await self.storage.get_refresh_token(user_id)
+                if not refresh_data:
+                    logger.info(f"No refresh token found for user {user_id}")
+                    return None
 
-            logger.info(
+                # storage.get_refresh_token() returns already-decrypted token
-                f"Generated background token for user {user_id} with scopes: {required_scopes}"
+                refresh_token = refresh_data["refresh_token"]
-            )
 
-            return access_token
+                # Get token with specific scopes for background operation
+                # Pass user_id to enable refresh token rotation storage
+                access_token, expires_in = await self._refresh_access_token_with_scopes(
+                    refresh_token, required_scopes, user_id=user_id
+                )
 
-        except Exception as e:
+                # Cache the background token
-            logger.error(f"Failed to get background token for user {user_id}: {e}")
+                await self.cache.set(cache_key, access_token, expires_in)
-            await self.cache.invalidate(cache_key)
-            return None
 
-    async def _refresh_access_token(self, refresh_token: str) -> Tuple[str, int]:
+                logger.info(
+                    f"Generated background token for user {user_id} with scopes: {required_scopes}"
+                )
+
+                return access_token
+
+            except Exception as e:
+                logger.error(
+                    f"Failed to get background token for user {user_id}: {e}",
+                    exc_info=True,
+                )
+                await self.cache.invalidate(cache_key)
+                return None
+
+            finally:
+                # Always clear the in-progress marker
+                await self.cache.invalidate(refresh_in_progress_key)
+
+    async def _refresh_access_token(
+        self, refresh_token: str, user_id: str | None = None
+    ) -> Tuple[str, int]:
         """
         Exchange refresh token for new access token.
 
@@ -313,20 +401,24 @@ class TokenBrokerService:
 
         Args:
             refresh_token: The refresh token
+            user_id: If provided, store the rotated refresh token for this user
 
         Returns:
             Tuple of (access_token, expires_in_seconds)
         """
         config = await self._get_oidc_config()
-        token_endpoint = config["token_endpoint"]
+        token_endpoint = self._rewrite_token_endpoint(config["token_endpoint"])
 
         client = await self._get_http_client()
 
         # Request new access token using refresh token
+        # Include client credentials as required by most OAuth servers
         data = {
             "grant_type": "refresh_token",
             "refresh_token": refresh_token,
-            "scope": "openid profile email notes:read notes:write calendar:read calendar:write",
+            "scope": "openid profile email offline_access notes:read notes:write calendar:read calendar:write",
+            "client_id": self.client_id,
+            "client_secret": self.client_secret,
         }
 
         response = await client.post(
@@ -345,42 +437,69 @@ class TokenBrokerService:
         access_token = token_data["access_token"]
         expires_in = token_data.get("expires_in", 3600)  # Default 1 hour
 
-        # Validate audience
+        # Handle refresh token rotation (Nextcloud OIDC rotates on every use)
-        await self._validate_token_audience(access_token, "nextcloud")
+        new_refresh_token = token_data.get("refresh_token")
+        if user_id and new_refresh_token and new_refresh_token != refresh_token:
+            # Calculate expiry as Unix timestamp (90 days from now)
+            expires_at = int(
+                (datetime.now(timezone.utc) + timedelta(days=90)).timestamp()
+            )
+            await self.storage.store_refresh_token(
+                user_id=user_id,
+                refresh_token=new_refresh_token,
+                expires_at=expires_at,
+            )
+            logger.info(f"Stored rotated refresh token for user {user_id}")
+
+        # Note: Nextcloud validates token audience on API calls - no need to pre-validate here
 
         logger.info(f"Refreshed access token (expires in {expires_in}s)")
         return access_token, expires_in
 
     async def _refresh_access_token_with_scopes(
-        self, refresh_token: str, required_scopes: list[str]
+        self, refresh_token: str, required_scopes: list[str], user_id: str | None = None
     ) -> Tuple[str, int]:
         """
         Exchange refresh token for new access token with specific scopes.
 
         This method implements scope downscoping for least privilege.
 
+        IMPORTANT: Nextcloud OIDC rotates refresh tokens on every use (one-time use).
+        When user_id is provided, this method stores the new refresh token returned
+        by Nextcloud to ensure subsequent refresh operations succeed.
+
         Args:
             refresh_token: The refresh token
             required_scopes: Minimal scopes needed for this operation
+            user_id: If provided, store the rotated refresh token for this user
 
         Returns:
             Tuple of (access_token, expires_in_seconds)
         """
         config = await self._get_oidc_config()
-        token_endpoint = config["token_endpoint"]
+        token_endpoint = self._rewrite_token_endpoint(config["token_endpoint"])
 
         client = await self._get_http_client()
 
-        # Always include basic OpenID scopes
+        # Always include basic OpenID scopes + offline_access to get new refresh token
-        scopes = list(set(["openid", "profile", "email"] + required_scopes))
+        scopes = list(
+            set(["openid", "profile", "email", "offline_access"] + required_scopes)
+        )
 
         # Request new access token with specific scopes
+        # Include client credentials as required by most OAuth servers
         data = {
             "grant_type": "refresh_token",
             "refresh_token": refresh_token,
             "scope": " ".join(scopes),
+            "client_id": self.client_id,
+            "client_secret": self.client_secret,
         }
 
+        logger.info(
+            f"Token refresh request to {token_endpoint} with client_id={self.client_id[:16]}..."
+        )
+
         response = await client.post(
             token_endpoint,
             data=data,
@@ -391,14 +510,29 @@ class TokenBrokerService:
             logger.error(
                 f"Token refresh with scopes failed: {response.status_code} - {response.text}"
             )
+            logger.error(f"  client_id used: {self.client_id[:16]}...")
             raise Exception(f"Token refresh failed: {response.status_code}")
 
         token_data = response.json()
         access_token = token_data["access_token"]
         expires_in = token_data.get("expires_in", 3600)  # Default 1 hour
 
-        # Validate audience
+        # Handle refresh token rotation (Nextcloud OIDC rotates on every use)
-        await self._validate_token_audience(access_token, "nextcloud")
+        new_refresh_token = token_data.get("refresh_token")
+        if user_id and new_refresh_token and new_refresh_token != refresh_token:
+            # Store the new refresh token for future use
+            # Calculate expiry as Unix timestamp (90 days from now)
+            expires_at = int(
+                (datetime.now(timezone.utc) + timedelta(days=90)).timestamp()
+            )
+            await self.storage.store_refresh_token(
+                user_id=user_id,
+                refresh_token=new_refresh_token,
+                expires_at=expires_at,
+            )
+            logger.info(f"Stored rotated refresh token for user {user_id}")
+
+        # Note: Nextcloud validates token audience on API calls - no need to pre-validate here
 
         logger.info(
             f"Refreshed access token with scopes {scopes} (expires in {expires_in}s)"
@@ -453,11 +587,8 @@ class TokenBrokerService:
             return False
 
         try:
-            # Decrypt current refresh token
+            # storage.get_refresh_token() returns already-decrypted token
-            encrypted_token = refresh_data["refresh_token"]
+            current_refresh_token = refresh_data["refresh_token"]
-            current_refresh_token = self.fernet.decrypt(
-                encrypted_token.encode()
-            ).decode()
 
             # Get OIDC configuration
             config = await self._get_oidc_config()
@@ -486,13 +617,15 @@ class TokenBrokerService:
             new_refresh_token = token_data.get("refresh_token")
 
             if new_refresh_token and new_refresh_token != current_refresh_token:
-                # Encrypt and store new refresh token
+                # storage.store_refresh_token() handles encryption internally
-                encrypted_new = self.fernet.encrypt(new_refresh_token.encode()).decode()
+                # Convert datetime to Unix timestamp (int) for database storage
+                expires_at = int(
+                    (datetime.now(timezone.utc) + timedelta(days=90)).timestamp()
+                )
                 await self.storage.store_refresh_token(
                     user_id=user_id,
-                    refresh_token=encrypted_new,
+                    refresh_token=new_refresh_token,
-                    expires_at=datetime.now(timezone.utc)
+                    expires_at=expires_at,
-                    + timedelta(days=90),  # 90-day expiry
                 )
                 logger.info(f"Rotated master refresh token for user {user_id}")
 
@@ -536,11 +669,8 @@ class TokenBrokerService:
             refresh_data = await self.storage.get_refresh_token(user_id)
             if refresh_data:
                 try:
-                    # Attempt to revoke at IdP
+                    # storage.get_refresh_token() returns already-decrypted token
-                    encrypted_token = refresh_data["refresh_token"]
+                    refresh_token = refresh_data["refresh_token"]
-                    refresh_token = self.fernet.decrypt(
-                        encrypted_token.encode()
-                    ).decode()
                     await self._revoke_token_at_idp(refresh_token)
                 except Exception as e:
                     logger.warning(f"Failed to revoke at IdP: {e}")

nextcloud_mcp_server/auth/unified_verifier.py

@@ -303,10 +303,13 @@ class UnifiedTokenVerifier(TokenVerifier):
 
         try:
             # Introspection requires client authentication
+            client_id = self.settings.oidc_client_id
+            client_secret = self.settings.oidc_client_secret
+            assert client_id is not None and client_secret is not None
             response = await self.http_client.post(
                 self.introspection_uri,
                 data={"token": token},
-                auth=(self.settings.oidc_client_id, self.settings.oidc_client_secret),
+                auth=(client_id, client_secret),
             )
 
             if response.status_code == 200:

nextcloud_mcp_server/auth/viz_routes.py

@@ -298,6 +298,7 @@ async def vector_visualization_search(request: Request) -> JSONResponse:
                             "title": r.title,
                             "excerpt": r.excerpt,
                             "score": r.score,
+                            "metadata": r.metadata,
                         }
                         for r in search_results
                     ],
@@ -458,6 +459,7 @@ async def vector_visualization_search(request: Request) -> JSONResponse:
                 ),  # Raw score from algorithm
                 "chunk_start_offset": r.chunk_start_offset,
                 "chunk_end_offset": r.chunk_end_offset,
+                "metadata": r.metadata,  # Include metadata (e.g., board_id for deck_card)
             }
             for r in search_results
         ]

nextcloud_mcp_server/auth/webhook_routes.py

@@ -139,6 +139,7 @@ async def _get_authenticated_client(request: Request) -> httpx.AsyncClient:
             raise RuntimeError("BasicAuth credentials not configured")
 
         assert nextcloud_host is not None  # Type narrowing for type checker
+        assert username is not None and password is not None  # Type narrowing
         return httpx.AsyncClient(
             base_url=nextcloud_host,
             auth=(username, password),

nextcloud_mcp_server/cli.py

@@ -253,5 +253,195 @@ def run(
     )
 
 
+@click.group()
+def db():
+    """Database migration management commands."""
+    pass
+
+
+@db.command()
+@click.option(
+    "--database-path",
+    "-d",
+    envvar="TOKEN_STORAGE_DB",
+    default="/app/data/tokens.db",
+    show_default=True,
+    help="Path to token storage database (can also use TOKEN_STORAGE_DB env var)",
+)
+@click.option(
+    "--revision",
+    "-r",
+    default="head",
+    show_default=True,
+    help="Target revision (default: head for latest)",
+)
+def upgrade(database_path: str, revision: str):
+    """Upgrade database to a specific revision.
+
+    \b
+    Examples:
+      # Upgrade to latest version
+      $ nextcloud-mcp-server db upgrade
+
+      # Upgrade to specific revision
+      $ nextcloud-mcp-server db upgrade --revision 001
+
+      # Use custom database path
+      $ nextcloud-mcp-server db upgrade -d /path/to/tokens.db
+    """
+    from nextcloud_mcp_server.migrations import upgrade_database
+
+    try:
+        click.echo(f"Upgrading database to revision: {revision}")
+        upgrade_database(database_path, revision)
+        click.echo(click.style("✓ Database upgraded successfully", fg="green"))
+    except Exception as e:
+        click.echo(click.style(f"✗ Upgrade failed: {e}", fg="red"), err=True)
+        raise click.ClickException(str(e))
+
+
+@db.command()
+@click.option(
+    "--database-path",
+    "-d",
+    envvar="TOKEN_STORAGE_DB",
+    default="/app/data/tokens.db",
+    show_default=True,
+    help="Path to token storage database",
+)
+@click.option(
+    "--revision",
+    "-r",
+    default="-1",
+    show_default=True,
+    help="Target revision (default: -1 for previous version)",
+)
+@click.confirmation_option(
+    prompt="Are you sure you want to downgrade the database? This may result in data loss."
+)
+def downgrade(database_path: str, revision: str):
+    """Downgrade database to a specific revision.
+
+    WARNING: This may result in data loss! Use with caution.
+
+    \b
+    Examples:
+      # Downgrade by one version
+      $ nextcloud-mcp-server db downgrade
+
+      # Downgrade to specific revision
+      $ nextcloud-mcp-server db downgrade --revision 001
+
+      # Downgrade to base (empty database)
+      $ nextcloud-mcp-server db downgrade --revision base
+    """
+    from nextcloud_mcp_server.migrations import downgrade_database
+
+    try:
+        click.echo(f"Downgrading database to revision: {revision}")
+        downgrade_database(database_path, revision)
+        click.echo(click.style("✓ Database downgraded successfully", fg="green"))
+    except Exception as e:
+        click.echo(click.style(f"✗ Downgrade failed: {e}", fg="red"), err=True)
+        raise click.ClickException(str(e))
+
+
+@db.command()
+@click.option(
+    "--database-path",
+    "-d",
+    envvar="TOKEN_STORAGE_DB",
+    default="/app/data/tokens.db",
+    show_default=True,
+    help="Path to token storage database",
+)
+def current(database_path: str):
+    """Show current database revision.
+
+    \b
+    Example:
+      $ nextcloud-mcp-server db current
+    """
+    from nextcloud_mcp_server.migrations import get_current_revision
+
+    try:
+        revision = get_current_revision(database_path)
+        if revision:
+            click.echo(f"Current revision: {click.style(revision, fg='cyan')}")
+        else:
+            click.echo(
+                click.style(
+                    "Database is not versioned (no alembic_version table)", fg="yellow"
+                )
+            )
+    except Exception as e:
+        click.echo(
+            click.style(f"✗ Failed to get current revision: {e}", fg="red"), err=True
+        )
+        raise click.ClickException(str(e))
+
+
+@db.command()
+@click.option(
+    "--database-path",
+    "-d",
+    envvar="TOKEN_STORAGE_DB",
+    default="/app/data/tokens.db",
+    show_default=True,
+    help="Path to token storage database",
+)
+def history(database_path: str):
+    """Show migration history.
+
+    \b
+    Example:
+      $ nextcloud-mcp-server db history
+    """
+    from nextcloud_mcp_server.migrations import show_migration_history
+
+    try:
+        click.echo("Migration history:")
+        show_migration_history(database_path)
+    except Exception as e:
+        click.echo(click.style(f"✗ Failed to show history: {e}", fg="red"), err=True)
+        raise click.ClickException(str(e))
+
+
+@db.command()
+@click.argument("message")
+def migrate(message: str):
+    """Create a new migration script (developers only).
+
+    The MESSAGE argument describes the changes in this migration.
+
+    \b
+    Examples:
+      $ nextcloud-mcp-server db migrate "add user preferences table"
+      $ nextcloud-mcp-server db migrate "add index on refresh_tokens.user_id"
+
+    Note: You must manually edit the generated migration file to add SQL statements.
+    """
+    from nextcloud_mcp_server.migrations import create_migration
+
+    try:
+        click.echo(f"Creating new migration: {message}")
+        create_migration(message)
+        click.echo(click.style("✓ Migration created successfully", fg="green"))
+        click.echo(
+            "Edit the migration file in alembic/versions/ to add upgrade/downgrade SQL."
+        )
+    except Exception as e:
+        click.echo(
+            click.style(f"✗ Failed to create migration: {e}", fg="red"), err=True
+        )
+        raise click.ClickException(str(e))
+
+
+# Create CLI group with subcommands
+cli = click.Group()
+cli.add_command(run)
+cli.add_command(db)
+
+
 if __name__ == "__main__":
-    run()
+    cli()

nextcloud_mcp_server/client/__init__.py

@@ -18,6 +18,7 @@ from .contacts import ContactsClient
 from .cookbook import CookbookClient
 from .deck import DeckClient
 from .groups import GroupsClient
+from .news import NewsClient
 from .notes import NotesClient
 from .sharing import SharingClient
 from .tables import TablesClient
@@ -81,6 +82,7 @@ class NextcloudClient:
         self.contacts = ContactsClient(self._client, username)
         self.cookbook = CookbookClient(self._client, username)
         self.deck = DeckClient(self._client, username)
+        self.news = NewsClient(self._client, username)
         self.users = UsersClient(self._client, username)
         self.groups = GroupsClient(self._client, username)
         self.sharing = SharingClient(self._client, username)

nextcloud_mcp_server/client/news.py

@@ -0,0 +1,394 @@
+"""Client for Nextcloud News app operations."""
+
+import logging
+from enum import IntEnum
+from typing import Any
+
+from .base import BaseNextcloudClient
+
+logger = logging.getLogger(__name__)
+
+
+class NewsItemType(IntEnum):
+    """Type constants for News API item queries."""
+
+    FEED = 0  # Single feed
+    FOLDER = 1  # Folder and its feeds
+    STARRED = 2  # All starred items
+    ALL = 3  # All items
+
+
+class NewsClient(BaseNextcloudClient):
+    """Client for Nextcloud News app operations."""
+
+    app_name = "news"
+    API_BASE = "/apps/news/api/v1-3"
+
+    # --- Folders ---
+
+    async def get_folders(self) -> list[dict[str, Any]]:
+        """Get all folders."""
+        response = await self._make_request("GET", f"{self.API_BASE}/folders")
+        return response.json().get("folders", [])
+
+    async def create_folder(self, name: str) -> dict[str, Any]:
+        """Create a new folder.
+
+        Args:
+            name: Folder name
+
+        Returns:
+            Created folder data
+
+        Raises:
+            HTTPStatusError: 409 if folder name already exists,
+                            422 if name is empty
+        """
+        response = await self._make_request(
+            "POST", f"{self.API_BASE}/folders", json={"name": name}
+        )
+        folders = response.json().get("folders", [])
+        return folders[0] if folders else {}
+
+    async def rename_folder(self, folder_id: int, name: str) -> None:
+        """Rename a folder.
+
+        Args:
+            folder_id: Folder ID
+            name: New folder name
+
+        Raises:
+            HTTPStatusError: 404 if folder not found, 409 if name exists
+        """
+        await self._make_request(
+            "PUT", f"{self.API_BASE}/folders/{folder_id}", json={"name": name}
+        )
+
+    async def delete_folder(self, folder_id: int) -> None:
+        """Delete a folder and all its feeds/items.
+
+        Args:
+            folder_id: Folder ID
+
+        Raises:
+            HTTPStatusError: 404 if folder not found
+        """
+        await self._make_request("DELETE", f"{self.API_BASE}/folders/{folder_id}")
+
+    async def mark_folder_read(self, folder_id: int, newest_item_id: int) -> None:
+        """Mark all items in a folder as read.
+
+        Args:
+            folder_id: Folder ID
+            newest_item_id: ID of newest item to mark read (prevents marking
+                           items user hasn't seen yet)
+
+        Raises:
+            HTTPStatusError: 404 if folder not found
+        """
+        await self._make_request(
+            "POST",
+            f"{self.API_BASE}/folders/{folder_id}/read",
+            json={"newestItemId": newest_item_id},
+        )
+
+    # --- Feeds ---
+
+    async def get_feeds(self) -> dict[str, Any]:
+        """Get all feeds with metadata.
+
+        Returns:
+            Dict with keys:
+                - feeds: List of feed objects
+                - starredCount: Number of starred items
+                - newestItemId: ID of newest item (omitted if no items)
+        """
+        response = await self._make_request("GET", f"{self.API_BASE}/feeds")
+        return response.json()
+
+    async def create_feed(
+        self, url: str, folder_id: int | None = None
+    ) -> dict[str, Any]:
+        """Subscribe to a new feed.
+
+        Args:
+            url: Feed URL
+            folder_id: Optional folder ID (None for root)
+
+        Returns:
+            Created feed data
+
+        Raises:
+            HTTPStatusError: 409 if feed already exists, 422 if URL is invalid
+        """
+        body: dict[str, Any] = {"url": url}
+        if folder_id is not None:
+            body["folderId"] = folder_id
+        response = await self._make_request("POST", f"{self.API_BASE}/feeds", json=body)
+        data = response.json()
+        feeds = data.get("feeds", [])
+        return feeds[0] if feeds else {}
+
+    async def delete_feed(self, feed_id: int) -> None:
+        """Unsubscribe from a feed (deletes all items).
+
+        Args:
+            feed_id: Feed ID
+
+        Raises:
+            HTTPStatusError: 404 if feed not found
+        """
+        await self._make_request("DELETE", f"{self.API_BASE}/feeds/{feed_id}")
+
+    async def move_feed(self, feed_id: int, folder_id: int | None) -> None:
+        """Move a feed to a different folder.
+
+        Args:
+            feed_id: Feed ID
+            folder_id: Target folder ID (None for root)
+
+        Raises:
+            HTTPStatusError: 404 if feed not found
+        """
+        await self._make_request(
+            "POST",
+            f"{self.API_BASE}/feeds/{feed_id}/move",
+            json={"folderId": folder_id},
+        )
+
+    async def rename_feed(self, feed_id: int, title: str) -> None:
+        """Rename a feed.
+
+        Args:
+            feed_id: Feed ID
+            title: New feed title
+
+        Raises:
+            HTTPStatusError: 404 if feed not found
+        """
+        await self._make_request(
+            "POST",
+            f"{self.API_BASE}/feeds/{feed_id}/rename",
+            json={"feedTitle": title},
+        )
+
+    async def mark_feed_read(self, feed_id: int, newest_item_id: int) -> None:
+        """Mark all items in a feed as read.
+
+        Args:
+            feed_id: Feed ID
+            newest_item_id: ID of newest item to mark read
+
+        Raises:
+            HTTPStatusError: 404 if feed not found
+        """
+        await self._make_request(
+            "POST",
+            f"{self.API_BASE}/feeds/{feed_id}/read",
+            json={"newestItemId": newest_item_id},
+        )
+
+    # --- Items ---
+
+    async def get_items(
+        self,
+        batch_size: int = 50,
+        offset: int = 0,
+        type_: int = NewsItemType.ALL,
+        id_: int = 0,
+        get_read: bool = True,
+        oldest_first: bool = False,
+    ) -> list[dict[str, Any]]:
+        """Get items (articles) with filtering.
+
+        Args:
+            batch_size: Number of items to return (-1 for all)
+            offset: Item ID to start after (for pagination)
+            type_: Item type filter (NewsItemType)
+            id_: Feed/folder ID (ignored for STARRED/ALL types)
+            get_read: Include read items
+            oldest_first: Sort oldest first instead of newest
+
+        Returns:
+            List of item objects
+        """
+        params: dict[str, Any] = {
+            "batchSize": batch_size,
+            "offset": offset,
+            "type": type_,
+            "id": id_,
+            "getRead": str(get_read).lower(),
+            "oldestFirst": str(oldest_first).lower(),
+        }
+        response = await self._make_request(
+            "GET", f"{self.API_BASE}/items", params=params
+        )
+        return response.json().get("items", [])
+
+    async def get_item(self, item_id: int) -> dict[str, Any]:
+        """Get a specific item by ID.
+
+        Note: The News API doesn't have a direct single-item endpoint,
+        so we fetch all items and filter. For efficiency, consider
+        caching or using get_items with specific feed if known.
+
+        Args:
+            item_id: Item ID
+
+        Returns:
+            Item data
+
+        Raises:
+            ValueError: If item not found
+        """
+        # Fetch all items and find the one we need
+        # This is inefficient but the API doesn't provide a direct endpoint
+        items = await self.get_items(batch_size=-1, get_read=True)
+        for item in items:
+            if item.get("id") == item_id:
+                return item
+        raise ValueError(f"Item {item_id} not found")
+
+    async def get_updated_items(
+        self,
+        last_modified: int,
+        type_: int = NewsItemType.ALL,
+        id_: int = 0,
+    ) -> list[dict[str, Any]]:
+        """Get items modified since a timestamp (for delta sync).
+
+        Args:
+            last_modified: Unix timestamp (seconds or microseconds)
+            type_: Item type filter
+            id_: Feed/folder ID
+
+        Returns:
+            List of modified items (includes deleted items)
+        """
+        params: dict[str, Any] = {
+            "lastModified": last_modified,
+            "type": type_,
+            "id": id_,
+        }
+        response = await self._make_request(
+            "GET", f"{self.API_BASE}/items/updated", params=params
+        )
+        return response.json().get("items", [])
+
+    async def mark_item_read(self, item_id: int) -> None:
+        """Mark a single item as read.
+
+        Args:
+            item_id: Item ID
+
+        Raises:
+            HTTPStatusError: 404 if item not found
+        """
+        await self._make_request("POST", f"{self.API_BASE}/items/{item_id}/read")
+
+    async def mark_item_unread(self, item_id: int) -> None:
+        """Mark a single item as unread.
+
+        Args:
+            item_id: Item ID
+
+        Raises:
+            HTTPStatusError: 404 if item not found
+        """
+        await self._make_request("POST", f"{self.API_BASE}/items/{item_id}/unread")
+
+    async def star_item(self, item_id: int) -> None:
+        """Star (favorite) a single item.
+
+        Args:
+            item_id: Item ID
+
+        Raises:
+            HTTPStatusError: 404 if item not found
+        """
+        await self._make_request("POST", f"{self.API_BASE}/items/{item_id}/star")
+
+    async def unstar_item(self, item_id: int) -> None:
+        """Unstar a single item.
+
+        Args:
+            item_id: Item ID
+
+        Raises:
+            HTTPStatusError: 404 if item not found
+        """
+        await self._make_request("POST", f"{self.API_BASE}/items/{item_id}/unstar")
+
+    async def mark_items_read(self, item_ids: list[int]) -> None:
+        """Mark multiple items as read.
+
+        Args:
+            item_ids: List of item IDs
+        """
+        await self._make_request(
+            "POST", f"{self.API_BASE}/items/read/multiple", json={"itemIds": item_ids}
+        )
+
+    async def mark_items_unread(self, item_ids: list[int]) -> None:
+        """Mark multiple items as unread.
+
+        Args:
+            item_ids: List of item IDs
+        """
+        await self._make_request(
+            "POST",
+            f"{self.API_BASE}/items/unread/multiple",
+            json={"itemIds": item_ids},
+        )
+
+    async def star_items(self, item_ids: list[int]) -> None:
+        """Star multiple items.
+
+        Args:
+            item_ids: List of item IDs
+        """
+        await self._make_request(
+            "POST", f"{self.API_BASE}/items/star/multiple", json={"itemIds": item_ids}
+        )
+
+    async def unstar_items(self, item_ids: list[int]) -> None:
+        """Unstar multiple items.
+
+        Args:
+            item_ids: List of item IDs
+        """
+        await self._make_request(
+            "POST",
+            f"{self.API_BASE}/items/unstar/multiple",
+            json={"itemIds": item_ids},
+        )
+
+    async def mark_all_read(self, newest_item_id: int) -> None:
+        """Mark all items as read.
+
+        Args:
+            newest_item_id: ID of newest item to mark read
+        """
+        await self._make_request(
+            "POST", f"{self.API_BASE}/items/read", json={"newestItemId": newest_item_id}
+        )
+
+    # --- Status ---
+
+    async def get_status(self) -> dict[str, Any]:
+        """Get News app status and configuration.
+
+        Returns:
+            Dict with version and warnings
+        """
+        response = await self._make_request("GET", f"{self.API_BASE}/status")
+        return response.json()
+
+    async def get_version(self) -> str:
+        """Get News app version.
+
+        Returns:
+            Version string (e.g., "25.0.0")
+        """
+        response = await self._make_request("GET", f"{self.API_BASE}/version")
+        return response.json().get("version", "")

nextcloud_mcp_server/client/webdav.py

@@ -1174,13 +1174,17 @@ class WebDAVClient(BaseNextcloudClient):
 
             if display_name_elem is not None and display_name_elem.text == tag_name:
                 tag_info = {
-                    "id": int(tag_id_elem.text) if tag_id_elem is not None else None,
+                    "id": int(tag_id_elem.text)
+                    if tag_id_elem is not None and tag_id_elem.text is not None
+                    else None,
                     "name": display_name_elem.text,
                     "userVisible": user_visible_elem.text.lower() == "true"
                     if user_visible_elem is not None
+                    and user_visible_elem.text is not None
                     else True,
                     "userAssignable": user_assignable_elem.text.lower() == "true"
                     if user_assignable_elem is not None
+                    and user_assignable_elem.text is not None
                     else True,
                 }
                 logger.debug(f"Found tag '{tag_name}' with ID {tag_info['id']}")
@@ -1369,7 +1373,9 @@ class WebDAVClient(BaseNextcloudClient):
         )
 
         file_info = {
-            "id": int(fileid_elem.text) if fileid_elem is not None else None,
+            "id": int(fileid_elem.text)
+            if fileid_elem is not None and fileid_elem.text is not None
+            else None,
             "path": path,
             "name": displayname_elem.text
             if displayname_elem is not None

nextcloud_mcp_server/config.py

@@ -163,6 +163,12 @@ def get_document_processor_config() -> dict[str, Any]:
 class Settings:
     """Application settings from environment variables."""
 
+    # Deployment mode (ADR-021: explicit mode selection)
+    # Optional: If not set, mode is auto-detected from other settings
+    # Valid values: single_user_basic, multi_user_basic, oauth_single_audience,
+    #               oauth_token_exchange, smithery
+    deployment_mode: Optional[str] = None
+
     # OAuth/OIDC settings
     oidc_discovery_url: Optional[str] = None
     oidc_client_id: Optional[str] = None
@@ -187,6 +193,11 @@ class Settings:
     enable_token_exchange: bool = False
     enable_offline_access: bool = False
 
+    # Multi-user BasicAuth pass-through mode (ADR-019 interim solution)
+    # When enabled, MCP server extracts BasicAuth credentials from request headers
+    # and passes them through to Nextcloud APIs (no storage, stateless)
+    enable_multi_user_basic_auth: bool = False
+
     # Token exchange cache settings
     token_exchange_cache_ttl: int = 300  # seconds (5 minutes default)
 
@@ -205,6 +216,7 @@ class Settings:
     vector_sync_scan_interval: int = 300  # seconds (5 minutes)
     vector_sync_processor_workers: int = 3
     vector_sync_queue_max_size: int = 10000
+    vector_sync_user_poll_interval: int = 60  # seconds - OAuth mode user discovery
 
     # Qdrant settings (mutually exclusive modes)
     qdrant_url: Optional[str] = None  # Network mode: http://qdrant:6333
@@ -345,13 +357,131 @@ class Settings:
         return f"{deployment_id}-{model_name}"
 
 
+def _get_semantic_search_enabled() -> bool:
+    """Get semantic search enabled status, supporting both old and new variable names.
+
+    Supports:
+    - ENABLE_SEMANTIC_SEARCH (new, preferred)
+    - VECTOR_SYNC_ENABLED (old, deprecated)
+
+    Returns:
+        True if semantic search should be enabled
+    """
+    logger = logging.getLogger(__name__)
+
+    new_value = os.getenv("ENABLE_SEMANTIC_SEARCH", "").lower() == "true"
+    old_value = os.getenv("VECTOR_SYNC_ENABLED", "").lower() == "true"
+
+    if new_value and old_value:
+        logger.warning(
+            "Both ENABLE_SEMANTIC_SEARCH and VECTOR_SYNC_ENABLED are set. "
+            "Using ENABLE_SEMANTIC_SEARCH. "
+            "VECTOR_SYNC_ENABLED is deprecated and will be removed in v1.0.0."
+        )
+    elif old_value and not new_value:
+        logger.warning(
+            "VECTOR_SYNC_ENABLED is deprecated. "
+            "Please use ENABLE_SEMANTIC_SEARCH instead. "
+            "Support for VECTOR_SYNC_ENABLED will be removed in v1.0.0."
+        )
+
+    return new_value or old_value
+
+
+def _is_multi_user_mode() -> bool:
+    """Detect if this is a multi-user deployment mode.
+
+    Multi-user modes are:
+    - Multi-user BasicAuth (ENABLE_MULTI_USER_BASIC_AUTH=true)
+    - OAuth Single-Audience (no username/password set)
+    - OAuth Token Exchange (ENABLE_TOKEN_EXCHANGE=true)
+
+    Single-user modes are:
+    - Single-user BasicAuth (username and password both set)
+    - Smithery Stateless (SMITHERY_DEPLOYMENT=true)
+
+    Returns:
+        True if multi-user mode detected
+    """
+    # Smithery is always single-user (stateless)
+    if os.getenv("SMITHERY_DEPLOYMENT", "false").lower() == "true":
+        return False
+
+    # Multi-user BasicAuth explicitly enabled
+    if os.getenv("ENABLE_MULTI_USER_BASIC_AUTH", "false").lower() == "true":
+        return True
+
+    # Token exchange implies OAuth multi-user
+    if os.getenv("ENABLE_TOKEN_EXCHANGE", "false").lower() == "true":
+        return True
+
+    # If both username and password are set, it's single-user BasicAuth
+    has_username = bool(os.getenv("NEXTCLOUD_USERNAME"))
+    has_password = bool(os.getenv("NEXTCLOUD_PASSWORD"))
+    if has_username and has_password:
+        return False
+
+    # Otherwise, assume OAuth multi-user (default when no credentials provided)
+    return True
+
+
+def _get_background_operations_enabled() -> bool:
+    """Get background operations enabled status with auto-enablement for semantic search.
+
+    Supports:
+    - ENABLE_BACKGROUND_OPERATIONS (new, preferred)
+    - ENABLE_OFFLINE_ACCESS (old, deprecated)
+    - Auto-enabled if ENABLE_SEMANTIC_SEARCH=true in multi-user modes
+
+    Returns:
+        True if background operations should be enabled
+    """
+    logger = logging.getLogger(__name__)
+
+    # Check new and old variable names
+    explicit = os.getenv("ENABLE_BACKGROUND_OPERATIONS", "").lower() == "true"
+    legacy = os.getenv("ENABLE_OFFLINE_ACCESS", "").lower() == "true"
+
+    if explicit and legacy:
+        logger.warning(
+            "Both ENABLE_BACKGROUND_OPERATIONS and ENABLE_OFFLINE_ACCESS are set. "
+            "Using ENABLE_BACKGROUND_OPERATIONS. "
+            "ENABLE_OFFLINE_ACCESS is deprecated and will be removed in v1.0.0."
+        )
+    elif legacy and not explicit:
+        logger.warning(
+            "ENABLE_OFFLINE_ACCESS is deprecated. "
+            "Please use ENABLE_BACKGROUND_OPERATIONS instead. "
+            "Support for ENABLE_OFFLINE_ACCESS will be removed in v1.0.0."
+        )
+
+    # Auto-enable if semantic search is enabled in multi-user mode
+    semantic_search_enabled = _get_semantic_search_enabled()
+    is_multi_user = _is_multi_user_mode()
+    auto_enabled = semantic_search_enabled and is_multi_user
+
+    if auto_enabled and not (explicit or legacy):
+        logger.info(
+            "Automatically enabled background operations for semantic search in multi-user mode. "
+            "Set ENABLE_BACKGROUND_OPERATIONS=false to disable (this will also disable semantic search)."
+        )
+
+    return explicit or legacy or auto_enabled
+
+
 def get_settings() -> Settings:
     """Get application settings from environment variables.
 
     Returns:
         Settings object with configuration values
     """
+    # Get consolidated values with smart dependency resolution
+    enable_semantic_search = _get_semantic_search_enabled()
+    enable_background_operations = _get_background_operations_enabled()
+
     return Settings(
+        # Deployment mode (ADR-021)
+        deployment_mode=os.getenv("MCP_DEPLOYMENT_MODE"),
         # OAuth/OIDC settings
         oidc_discovery_url=os.getenv("OIDC_DISCOVERY_URL"),
         oidc_client_id=os.getenv("NEXTCLOUD_OIDC_CLIENT_ID"),
@@ -372,8 +502,10 @@ def get_settings() -> Settings:
         enable_token_exchange=(
             os.getenv("ENABLE_TOKEN_EXCHANGE", "false").lower() == "true"
         ),
-        enable_offline_access=(
+        enable_offline_access=enable_background_operations,  # Smart dependency resolution
-            os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() == "true"
+        # Multi-user BasicAuth pass-through mode
+        enable_multi_user_basic_auth=(
+            os.getenv("ENABLE_MULTI_USER_BASIC_AUTH", "false").lower() == "true"
         ),
         # Token exchange cache settings
         token_exchange_cache_ttl=int(os.getenv("TOKEN_EXCHANGE_CACHE_TTL", "300")),
@@ -381,9 +513,7 @@ def get_settings() -> Settings:
         token_encryption_key=os.getenv("TOKEN_ENCRYPTION_KEY"),
         token_storage_db=os.getenv("TOKEN_STORAGE_DB", "/tmp/tokens.db"),
         # Vector sync settings (ADR-007)
-        vector_sync_enabled=(
+        vector_sync_enabled=enable_semantic_search,  # Smart dependency resolution
-            os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
-        ),
         vector_sync_scan_interval=int(os.getenv("VECTOR_SYNC_SCAN_INTERVAL", "300")),
         vector_sync_processor_workers=int(
             os.getenv("VECTOR_SYNC_PROCESSOR_WORKERS", "3")
@@ -391,6 +521,9 @@ def get_settings() -> Settings:
         vector_sync_queue_max_size=int(
             os.getenv("VECTOR_SYNC_QUEUE_MAX_SIZE", "10000")
         ),
+        vector_sync_user_poll_interval=int(
+            os.getenv("VECTOR_SYNC_USER_POLL_INTERVAL", "60")
+        ),
         # Qdrant settings
         qdrant_url=os.getenv("QDRANT_URL"),
         qdrant_location=os.getenv("QDRANT_LOCATION"),

nextcloud_mcp_server/config_validators.py

@@ -0,0 +1,460 @@
+"""Configuration validation and mode detection for the MCP server.
+
+This module provides:
+- Mode detection based on configuration
+- Configuration validation with clear error messages
+- Single source of truth for deployment mode requirements
+
+See ADR-020 for detailed architecture and deployment mode documentation.
+"""
+
+import logging
+from dataclasses import dataclass
+from enum import Enum
+
+from nextcloud_mcp_server.config import Settings
+
+logger = logging.getLogger(__name__)
+
+
+class AuthMode(Enum):
+    """Authentication mode for the MCP server.
+
+    Determines how users authenticate and how the server accesses Nextcloud.
+    """
+
+    SINGLE_USER_BASIC = "single_user_basic"
+    MULTI_USER_BASIC = "multi_user_basic"
+    OAUTH_SINGLE_AUDIENCE = "oauth_single"
+    OAUTH_TOKEN_EXCHANGE = "oauth_exchange"
+    SMITHERY_STATELESS = "smithery"
+
+
+@dataclass
+class ModeRequirements:
+    """Requirements for a deployment mode.
+
+    Attributes:
+        required: Configuration variables that must be set
+        optional: Configuration variables that may be set
+        forbidden: Configuration variables that should not be set
+        conditional: Additional requirements based on feature flags
+                     Format: {feature_flag: [required_vars]}
+        description: Human-readable description of the mode
+    """
+
+    required: list[str]
+    optional: list[str]
+    forbidden: list[str]
+    conditional: dict[str, list[str]]
+    description: str
+
+
+# Mode requirements definition
+MODE_REQUIREMENTS: dict[AuthMode, ModeRequirements] = {
+    AuthMode.SINGLE_USER_BASIC: ModeRequirements(
+        required=["nextcloud_host", "nextcloud_username", "nextcloud_password"],
+        optional=[
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+            "document_chunk_size",
+            "document_chunk_overlap",
+        ],
+        forbidden=[
+            "enable_multi_user_basic_auth",
+            "enable_token_exchange",
+            "oidc_client_id",
+            "oidc_client_secret",
+        ],
+        conditional={
+            "vector_sync_enabled": [
+                # Either qdrant_url OR qdrant_location (checked in Settings.__post_init__)
+                # At least one embedding provider (ollama_base_url OR openai_api_key)
+            ],
+        },
+        description="Single-user deployment with BasicAuth credentials. "
+        "Suitable for personal Nextcloud instances and local development.",
+    ),
+    AuthMode.MULTI_USER_BASIC: ModeRequirements(
+        required=["nextcloud_host", "enable_multi_user_basic_auth"],
+        optional=[
+            # Background sync with app passwords (via Astrolabe)
+            "enable_offline_access",
+            "token_encryption_key",
+            "token_storage_db",
+            "oidc_client_id",
+            "oidc_client_secret",
+            # Vector sync
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+        ],
+        forbidden=[
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_token_exchange",
+        ],
+        conditional={
+            "enable_offline_access": [
+                # OAuth credentials validated separately (lines 397-406) with clearer error message
+                "token_encryption_key",
+                "token_storage_db",
+            ],
+            # Note: vector_sync_enabled (now ENABLE_SEMANTIC_SEARCH) automatically
+            # enables background operations in multi-user modes. No explicit
+            # enable_offline_access setting required.
+        },
+        description="Multi-user deployment with BasicAuth pass-through. "
+        "Users provide credentials in request headers. "
+        "Optional background sync using app passwords stored via Astrolabe.",
+    ),
+    AuthMode.OAUTH_SINGLE_AUDIENCE: ModeRequirements(
+        required=["nextcloud_host"],
+        optional=[
+            # OAuth credentials (uses DCR if not provided)
+            "oidc_client_id",
+            "oidc_client_secret",
+            "oidc_discovery_url",
+            # Offline access
+            "enable_offline_access",
+            "token_encryption_key",
+            "token_storage_db",
+            # Vector sync
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+            # Scopes
+            "nextcloud_oidc_scopes",
+        ],
+        forbidden=[
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_token_exchange",
+            "enable_multi_user_basic_auth",
+        ],
+        conditional={
+            "enable_offline_access": [
+                "token_encryption_key",
+                "token_storage_db",
+            ],
+            # Note: vector_sync_enabled (now ENABLE_SEMANTIC_SEARCH) automatically
+            # enables background operations in multi-user modes. No explicit
+            # enable_offline_access setting required.
+        },
+        description="OAuth multi-user deployment with single-audience tokens. "
+        "Tokens work for both MCP server and Nextcloud APIs (pass-through). "
+        "Uses Dynamic Client Registration if credentials not provided.",
+    ),
+    AuthMode.OAUTH_TOKEN_EXCHANGE: ModeRequirements(
+        required=["nextcloud_host", "enable_token_exchange"],
+        optional=[
+            # OAuth credentials
+            "oidc_client_id",
+            "oidc_client_secret",
+            "oidc_discovery_url",
+            # Token exchange settings
+            "token_exchange_cache_ttl",
+            # Offline access
+            "enable_offline_access",
+            "token_encryption_key",
+            "token_storage_db",
+            # Vector sync
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+        ],
+        forbidden=[
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_multi_user_basic_auth",
+        ],
+        conditional={
+            "enable_offline_access": [
+                "token_encryption_key",
+                "token_storage_db",
+            ],
+            # Note: vector_sync_enabled (now ENABLE_SEMANTIC_SEARCH) automatically
+            # enables background operations in multi-user modes. No explicit
+            # enable_offline_access setting required.
+        },
+        description="OAuth multi-user deployment with token exchange (RFC 8693). "
+        "MCP tokens are separate from Nextcloud tokens. "
+        "Server exchanges MCP token for Nextcloud token on each request.",
+    ),
+    AuthMode.SMITHERY_STATELESS: ModeRequirements(
+        required=[],  # All config from session URL params
+        optional=[],
+        forbidden=[
+            "nextcloud_host",
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_multi_user_basic_auth",
+            "enable_token_exchange",
+            "enable_offline_access",
+            "vector_sync_enabled",
+            "oidc_client_id",
+            "oidc_client_secret",
+        ],
+        conditional={},
+        description="Stateless multi-tenant deployment for Smithery platform. "
+        "Configuration comes from session URL parameters. "
+        "No persistent storage, no OAuth, no vector sync.",
+    ),
+}
+
+
+def detect_auth_mode(settings: Settings) -> AuthMode:
+    """Detect authentication mode from configuration.
+
+    Mode detection priority (ADR-021):
+    0. Explicit MCP_DEPLOYMENT_MODE (if set) - NEW in ADR-021
+    1. Smithery (explicit flag)
+    2. Token exchange (most specific OAuth mode)
+    3. Multi-user BasicAuth
+    4. Single-user BasicAuth
+    5. OAuth single-audience (default OAuth mode)
+
+    Args:
+        settings: Application settings
+
+    Returns:
+        Detected AuthMode
+
+    Raises:
+        ValueError: If explicit deployment_mode is invalid or conflicts with detected mode
+    """
+    import logging
+    import os
+
+    logger = logging.getLogger(__name__)
+
+    # ADR-021: Check for explicit deployment mode first
+    if settings.deployment_mode:
+        mode_str = settings.deployment_mode.lower().strip()
+
+        # Map string to AuthMode enum
+        mode_map = {
+            "single_user_basic": AuthMode.SINGLE_USER_BASIC,
+            "multi_user_basic": AuthMode.MULTI_USER_BASIC,
+            "oauth_single_audience": AuthMode.OAUTH_SINGLE_AUDIENCE,
+            "oauth_token_exchange": AuthMode.OAUTH_TOKEN_EXCHANGE,
+            "smithery": AuthMode.SMITHERY_STATELESS,
+        }
+
+        if mode_str not in mode_map:
+            valid_modes = ", ".join(mode_map.keys())
+            raise ValueError(
+                f"Invalid MCP_DEPLOYMENT_MODE: '{settings.deployment_mode}'. "
+                f"Valid values: {valid_modes}"
+            )
+
+        explicit_mode = mode_map[mode_str]
+        logger.info(f"Using explicit deployment mode: {explicit_mode.value}")
+        return explicit_mode
+
+    # Auto-detection (existing behavior)
+    # Check for Smithery mode (explicit environment variable)
+    # Note: This checks the environment directly, not settings
+    # because Smithery mode has no settings-based config
+    if os.getenv("SMITHERY_DEPLOYMENT", "false").lower() == "true":
+        return AuthMode.SMITHERY_STATELESS
+
+    # Check for token exchange (most specific OAuth mode)
+    if settings.enable_token_exchange:
+        return AuthMode.OAUTH_TOKEN_EXCHANGE
+
+    # Check for multi-user BasicAuth
+    if settings.enable_multi_user_basic_auth:
+        return AuthMode.MULTI_USER_BASIC
+
+    # Check for single-user BasicAuth (explicit credentials)
+    if settings.nextcloud_username and settings.nextcloud_password:
+        return AuthMode.SINGLE_USER_BASIC
+
+    # Default: OAuth single-audience mode
+    # This is the safest multi-user mode (no credential storage)
+    return AuthMode.OAUTH_SINGLE_AUDIENCE
+
+
+def validate_configuration(settings: Settings) -> tuple[AuthMode, list[str]]:
+    """Validate configuration for detected mode.
+
+    Args:
+        settings: Application settings
+
+    Returns:
+        Tuple of (detected_mode, list_of_errors)
+        Empty list means valid configuration.
+    """
+    mode = detect_auth_mode(settings)
+    requirements = MODE_REQUIREMENTS[mode]
+    errors: list[str] = []
+
+    logger.debug(f"Validating configuration for mode: {mode.value}")
+
+    # Check required variables
+    for var in requirements.required:
+        value = getattr(settings, var, None)
+        if value is None or (isinstance(value, str) and not value.strip()):
+            errors.append(
+                f"[{mode.value}] Missing required configuration: {var.upper()}"
+            )
+
+    # Check forbidden variables
+    for var in requirements.forbidden:
+        value = getattr(settings, var, None)
+        # For bools, check if True (forbidden means must be False/unset)
+        # For strings, check if non-empty
+        is_set = False
+        if isinstance(value, bool):
+            is_set = value is True
+        elif isinstance(value, str):
+            is_set = bool(value.strip())
+        elif value is not None:
+            is_set = True
+
+        if is_set:
+            errors.append(
+                f"[{mode.value}] Forbidden configuration: {var.upper()} "
+                f"should not be set in this mode"
+            )
+
+    # Check conditional requirements
+    for condition, required_vars in requirements.conditional.items():
+        # Check if the condition is enabled
+        condition_value = getattr(settings, condition, None)
+        is_enabled = False
+
+        if isinstance(condition_value, bool):
+            is_enabled = condition_value is True
+        elif isinstance(condition_value, str):
+            is_enabled = bool(condition_value.strip())
+        elif condition_value is not None:
+            is_enabled = True
+
+        if is_enabled:
+            # Check that all required vars for this condition are set
+            for var in required_vars:
+                value = getattr(settings, var, None)
+
+                # For boolean requirements, check that they are True (not just set)
+                if hasattr(Settings, var):
+                    field_type = type(getattr(Settings(), var, None))
+                    if field_type is bool:
+                        if value is not True:
+                            errors.append(
+                                f"[{mode.value}] {var.upper()} must be enabled when "
+                                f"{condition.upper()} is enabled"
+                            )
+                        continue
+
+                # For non-boolean requirements, check that they are set
+                if value is None or (isinstance(value, str) and not value.strip()):
+                    errors.append(
+                        f"[{mode.value}] {var.upper()} is required when "
+                        f"{condition.upper()} is enabled"
+                    )
+
+    # Special validations for specific modes
+    if mode == AuthMode.SINGLE_USER_BASIC:
+        # Validate that NEXTCLOUD_HOST doesn't have trailing slash
+        if settings.nextcloud_host and settings.nextcloud_host.endswith("/"):
+            errors.append(
+                f"[{mode.value}] NEXTCLOUD_HOST should not have trailing slash: "
+                f"{settings.nextcloud_host}"
+            )
+
+    if mode in [
+        AuthMode.OAUTH_SINGLE_AUDIENCE,
+        AuthMode.OAUTH_TOKEN_EXCHANGE,
+    ]:
+        # If OAuth credentials not provided, DCR must be available
+        # (This is a runtime check, not a config check, so we just warn)
+        if not settings.oidc_client_id or not settings.oidc_client_secret:
+            logger.info(
+                f"[{mode.value}] OAuth credentials not configured. "
+                "Will attempt Dynamic Client Registration (DCR) at startup."
+            )
+
+    if mode == AuthMode.MULTI_USER_BASIC:
+        # If background operations enabled, check for OAuth credentials (for app password retrieval)
+        # Allow DCR as fallback, just like OAuth modes
+        if settings.enable_offline_access:
+            if not settings.oidc_client_id or not settings.oidc_client_secret:
+                logger.info(
+                    f"[{mode.value}] OAuth credentials not configured. "
+                    "Will attempt Dynamic Client Registration (DCR) at startup "
+                    "(required for app password retrieval via Astrolabe)."
+                )
+
+        # Note: Vector sync no longer requires explicit ENABLE_OFFLINE_ACCESS setting
+        # ENABLE_SEMANTIC_SEARCH (formerly VECTOR_SYNC_ENABLED) automatically enables
+        # background operations in multi-user modes via smart dependency resolution
+        # in config.py
+
+    # Note: Embedding provider validation removed - Simple provider is always
+    # available as fallback (ADR-015). Users can optionally configure Ollama or OpenAI
+    # for better quality embeddings.
+
+    return mode, errors
+
+
+def get_mode_summary(mode: AuthMode) -> str:
+    """Get human-readable summary of a deployment mode.
+
+    Args:
+        mode: Deployment mode
+
+    Returns:
+        Multi-line string describing the mode
+    """
+    requirements = MODE_REQUIREMENTS[mode]
+
+    summary_lines = [
+        f"Mode: {mode.value}",
+        f"Description: {requirements.description}",
+        "",
+        "Required configuration:",
+    ]
+
+    if requirements.required:
+        for var in requirements.required:
+            summary_lines.append(f"  - {var.upper()}")
+    else:
+        summary_lines.append("  (none - configured via session)")
+
+    summary_lines.append("")
+    summary_lines.append("Optional configuration:")
+
+    if requirements.optional:
+        for var in requirements.optional:
+            summary_lines.append(f"  - {var.upper()}")
+    else:
+        summary_lines.append("  (none)")
+
+    if requirements.conditional:
+        summary_lines.append("")
+        summary_lines.append("Conditional requirements:")
+        for condition, vars in requirements.conditional.items():
+            summary_lines.append(f"  When {condition.upper()} is enabled:")
+            for var in vars:
+                summary_lines.append(f"    - {var.upper()}")
+
+    return "\n".join(summary_lines)

nextcloud_mcp_server/context.py

@@ -67,6 +67,11 @@ async def get_client(ctx: Context) -> NextcloudClient:
         return _get_client_from_session_config(ctx)
 
     settings = get_settings()
+
+    # Multi-user BasicAuth pass-through mode - extract credentials from request
+    if settings.enable_multi_user_basic_auth:
+        return _get_client_from_basic_auth(ctx)
+
     lifespan_ctx = ctx.request_context.lifespan_context
 
     # BasicAuth mode - use shared client (no token exchange)
@@ -177,3 +182,67 @@ def _get_client_from_session_config(ctx: Context) -> NextcloudClient:
         username=username,
         auth=BasicAuth(username, app_password),
     )
+
+
+def _get_client_from_basic_auth(ctx: Context) -> NextcloudClient:
+    """
+    Create NextcloudClient from BasicAuth credentials in request headers.
+
+    For multi-user BasicAuth pass-through mode, this function extracts
+    username/password from the Authorization: Basic header (stored by
+    BasicAuthMiddleware) and creates a client that passes these credentials
+    through to Nextcloud APIs.
+
+    The credentials are NOT stored persistently - they exist only for the
+    duration of this request (stateless).
+
+    Args:
+        ctx: MCP request context with basic_auth in request state
+
+    Returns:
+        NextcloudClient configured with BasicAuth credentials
+
+    Raises:
+        ValueError: If BasicAuth credentials not found in request or if
+                   NEXTCLOUD_HOST is not configured
+    """
+    settings = get_settings()
+
+    # Validate that NEXTCLOUD_HOST is configured
+    if not settings.nextcloud_host:
+        raise ValueError(
+            "NEXTCLOUD_HOST environment variable must be set for multi-user BasicAuth mode"
+        )
+
+    # Extract BasicAuth credentials from request state (set by BasicAuthMiddleware)
+    # Access scope through the request object
+    scope = getattr(ctx.request_context.request, "scope", None)
+    if scope is None:
+        raise ValueError("Request scope not available in context")
+
+    request_state = scope.get("state", {})
+    basic_auth = request_state.get("basic_auth")
+
+    if not basic_auth:
+        raise ValueError(
+            "BasicAuth credentials not found in request. "
+            "Ensure Authorization: Basic header is provided with valid credentials."
+        )
+
+    username = basic_auth.get("username")
+    password = basic_auth.get("password")
+
+    if not username or not password:
+        raise ValueError("Invalid BasicAuth credentials - missing username or password")
+
+    logger.debug(
+        f"Creating multi-user BasicAuth client for {settings.nextcloud_host} as {username}"
+    )
+
+    # Create client that passes BasicAuth credentials through to Nextcloud
+    # settings.nextcloud_host is guaranteed to be str after the check above
+    return NextcloudClient(
+        base_url=settings.nextcloud_host,
+        username=username,
+        auth=BasicAuth(username, password),
+    )

nextcloud_mcp_server/migrations.py

@@ -0,0 +1,192 @@
+"""Database migration utilities for nextcloud-mcp-server.
+
+This module provides helper functions for managing Alembic database migrations
+programmatically. It enables automatic migration on application startup and
+provides CLI integration.
+"""
+
+import logging
+from pathlib import Path
+
+from alembic.config import Config
+
+from alembic import command
+
+logger = logging.getLogger(__name__)
+
+
+def get_alembic_config(database_path: str | Path | None = None) -> Config:
+    """
+    Get Alembic configuration for programmatic use.
+
+    Works in both development and installed (Docker) modes by using
+    package location instead of alembic.ini file.
+
+    Args:
+        database_path: Path to SQLite database file. If None, uses default
+                      (/app/data/tokens.db for Docker)
+
+    Returns:
+        Alembic Config object configured for the specified database
+    """
+    from nextcloud_mcp_server import alembic as alembic_package
+
+    # Use package location (works in both editable and installed modes)
+    if alembic_package.__file__ is None:
+        raise RuntimeError("alembic package __file__ is None")
+    script_location = Path(alembic_package.__file__).parent
+
+    # Create config programmatically (no alembic.ini needed at runtime)
+    config = Config()
+    config.set_main_option("script_location", str(script_location))
+    config.set_main_option("path_separator", "os")  # Suppress deprecation warning
+
+    # Set database URL
+    if database_path:
+        db_path = Path(database_path).resolve()
+    else:
+        db_path = Path("/app/data/tokens.db")  # Default for Docker
+
+    url = f"sqlite+aiosqlite:///{db_path}"
+    config.set_main_option("sqlalchemy.url", url)
+
+    logger.debug(f"Alembic script location: {script_location}")
+    logger.debug(f"Database: {db_path}")
+
+    return config
+
+
+def upgrade_database(
+    database_path: str | Path | None = None, revision: str = "head"
+) -> None:
+    """
+    Upgrade database to a specific revision.
+
+    Args:
+        database_path: Path to SQLite database file
+        revision: Target revision (default: "head" for latest)
+    """
+    config = get_alembic_config(database_path)
+    logger.info(f"Upgrading database to revision: {revision}")
+    command.upgrade(config, revision)
+    logger.info("Database upgrade completed successfully")
+
+
+def downgrade_database(
+    database_path: str | Path | None = None, revision: str = "-1"
+) -> None:
+    """
+    Downgrade database to a specific revision.
+
+    Args:
+        database_path: Path to SQLite database file
+        revision: Target revision (default: "-1" for previous version)
+    """
+    config = get_alembic_config(database_path)
+    logger.warning(f"Downgrading database to revision: {revision}")
+    command.downgrade(config, revision)
+    logger.info("Database downgrade completed successfully")
+
+
+def get_current_revision(database_path: str | Path | None = None) -> str | None:
+    """
+    Get the current database revision by directly querying the alembic_version table.
+
+    Args:
+        database_path: Path to SQLite database file
+
+    Returns:
+        Current revision ID or None if not versioned
+    """
+    import sqlite3
+
+    if database_path is None:
+        database_path = "/app/data/tokens.db"
+
+    db_path = Path(database_path).resolve()
+
+    if not db_path.exists():
+        logger.debug(f"Database does not exist: {db_path}")
+        return None
+
+    try:
+        # Query alembic_version table directly
+        conn = sqlite3.connect(str(db_path))
+        cursor = conn.cursor()
+
+        # Check if alembic_version table exists
+        cursor.execute(
+            "SELECT name FROM sqlite_master WHERE type='table' AND name='alembic_version'"
+        )
+        has_table = cursor.fetchone() is not None
+
+        if not has_table:
+            conn.close()
+            return None
+
+        # Get current version
+        cursor.execute("SELECT version_num FROM alembic_version")
+        row = cursor.fetchone()
+        conn.close()
+
+        return row[0] if row else None
+
+    except Exception as e:
+        logger.error(f"Failed to get current revision: {e}")
+        return None
+
+
+def stamp_database(
+    database_path: str | Path | None = None, revision: str = "head"
+) -> None:
+    """
+    Stamp database with a specific revision without running migrations.
+
+    This is useful for marking existing databases that were created before
+    Alembic was introduced. It tells Alembic "this database is at revision X"
+    without actually running the migration.
+
+    Args:
+        database_path: Path to SQLite database file
+        revision: Revision to stamp (default: "head" for latest)
+    """
+    config = get_alembic_config(database_path)
+    logger.info(f"Stamping database with revision: {revision}")
+    command.stamp(config, revision)
+    logger.info("Database stamped successfully")
+
+
+def show_migration_history(database_path: str | Path | None = None) -> None:
+    """
+    Display migration history.
+
+    Args:
+        database_path: Path to SQLite database file
+    """
+    config = get_alembic_config(database_path)
+    command.history(config, verbose=True)
+
+
+def create_migration(message: str, autogenerate: bool = False) -> None:
+    """
+    Create a new migration script.
+
+    Args:
+        message: Description of the migration
+        autogenerate: Whether to attempt auto-generation (requires SQLAlchemy models)
+
+    Note:
+        Since we don't use SQLAlchemy models, autogenerate will be disabled
+        and migrations must be written manually.
+    """
+    config = get_alembic_config()
+    logger.info(f"Creating new migration: {message}")
+
+    if autogenerate:
+        logger.warning(
+            "Auto-generation is not supported (no SQLAlchemy models). "
+            "Migration will be created with empty upgrade/downgrade functions."
+        )
+
+    command.revision(config, message=message, autogenerate=False)
+    logger.info("Migration created successfully. Edit the file to add SQL statements.")

nextcloud_mcp_server/models/news.py

@@ -0,0 +1,170 @@
+"""Pydantic models for Nextcloud News app responses."""
+
+from typing import List
+
+from pydantic import BaseModel, ConfigDict, Field
+
+from .base import BaseResponse
+
+
+class NewsFolder(BaseModel):
+    """Model for a News folder."""
+
+    model_config = ConfigDict(populate_by_name=True)
+
+    id: int = Field(description="Folder ID")
+    name: str = Field(description="Folder name")
+
+
+class NewsFeed(BaseModel):
+    """Model for a News feed (RSS/Atom subscription)."""
+
+    model_config = ConfigDict(populate_by_name=True)
+
+    id: int = Field(description="Feed ID")
+    url: str = Field(description="Feed URL")
+    title: str = Field(description="Feed title")
+    favicon_link: str | None = Field(
+        None, alias="faviconLink", description="Favicon URL"
+    )
+    link: str | None = Field(None, description="Website link")
+    added: int = Field(description="Unix timestamp when feed was added")
+    folder_id: int | None = Field(
+        None, alias="folderId", description="Parent folder ID"
+    )
+    unread_count: int = Field(
+        0, alias="unreadCount", description="Number of unread items"
+    )
+    ordering: int = Field(
+        0, description="Feed ordering (0=default, 1=oldest, 2=newest)"
+    )
+    pinned: bool = Field(False, description="Whether feed is pinned to top")
+    update_error_count: int = Field(
+        0, alias="updateErrorCount", description="Consecutive update failures"
+    )
+    last_update_error: str | None = Field(
+        None, alias="lastUpdateError", description="Last update error message"
+    )
+
+    @property
+    def has_errors(self) -> bool:
+        """Check if feed has update errors."""
+        return self.update_error_count > 0
+
+
+class NewsItem(BaseModel):
+    """Model for a News item (article) with full content."""
+
+    model_config = ConfigDict(populate_by_name=True)
+
+    id: int = Field(description="Item ID")
+    guid: str = Field(description="Globally unique identifier")
+    guid_hash: str = Field(alias="guidHash", description="MD5 hash of GUID")
+    url: str | None = Field(None, description="Article URL")
+    title: str = Field(description="Article title")
+    author: str | None = Field(None, description="Article author")
+    pub_date: int | None = Field(
+        None, alias="pubDate", description="Publication timestamp"
+    )
+    body: str | None = Field(None, description="Article content (HTML)")
+    enclosure_mime: str | None = Field(
+        None, alias="enclosureMime", description="Enclosure MIME type"
+    )
+    enclosure_link: str | None = Field(
+        None, alias="enclosureLink", description="Enclosure URL"
+    )
+    media_thumbnail: str | None = Field(
+        None, alias="mediaThumbnail", description="Media thumbnail URL"
+    )
+    media_description: str | None = Field(
+        None, alias="mediaDescription", description="Media description"
+    )
+    feed_id: int = Field(alias="feedId", description="Parent feed ID")
+    unread: bool = Field(True, description="Whether item is unread")
+    starred: bool = Field(False, description="Whether item is starred")
+    rtl: bool = Field(False, description="Right-to-left text")
+    last_modified: int = Field(
+        alias="lastModified", description="Last modification timestamp"
+    )
+    fingerprint: str | None = Field(
+        None, description="Content fingerprint for deduplication"
+    )
+    content_hash: str | None = Field(
+        None, alias="contentHash", description="Content hash"
+    )
+
+
+class NewsItemSummary(BaseModel):
+    """Lightweight model for News item list responses."""
+
+    model_config = ConfigDict(populate_by_name=True)
+
+    id: int = Field(description="Item ID")
+    title: str = Field(description="Article title")
+    feed_id: int = Field(alias="feedId", description="Parent feed ID")
+    unread: bool = Field(True, description="Whether item is unread")
+    starred: bool = Field(False, description="Whether item is starred")
+    pub_date: int | None = Field(
+        None, alias="pubDate", description="Publication timestamp"
+    )
+    url: str | None = Field(None, description="Article URL")
+    author: str | None = Field(None, description="Article author")
+
+
+class NewsStatus(BaseModel):
+    """Model for News app status."""
+
+    version: str = Field(description="News app version")
+    warnings: dict = Field(default_factory=dict, description="Configuration warnings")
+
+
+# --- Response Models ---
+
+
+class ListFoldersResponse(BaseResponse):
+    """Response model for listing folders."""
+
+    results: List[NewsFolder] = Field(description="List of folders")
+    total_count: int = Field(description="Total number of folders")
+
+
+class ListFeedsResponse(BaseResponse):
+    """Response model for listing feeds."""
+
+    results: List[NewsFeed] = Field(description="List of feeds")
+    starred_count: int = Field(0, description="Number of starred items")
+    newest_item_id: int | None = Field(None, description="ID of newest item")
+    total_count: int = Field(description="Total number of feeds")
+
+
+class ListItemsResponse(BaseResponse):
+    """Response model for listing items."""
+
+    results: List[NewsItemSummary] = Field(description="List of items")
+    total_count: int = Field(description="Number of items returned")
+    has_more: bool = Field(False, description="Whether more items exist")
+    oldest_id: int | None = Field(None, description="Oldest item ID (for pagination)")
+
+
+class GetItemResponse(BaseResponse):
+    """Response model for getting a single item."""
+
+    item: NewsItem = Field(description="Full item details")
+
+
+class FeedHealthResponse(BaseResponse):
+    """Response model for feed health status."""
+
+    feed_id: int = Field(description="Feed ID")
+    title: str = Field(description="Feed title")
+    url: str = Field(description="Feed URL")
+    has_errors: bool = Field(description="Whether feed has update errors")
+    error_count: int = Field(description="Number of consecutive errors")
+    last_error: str | None = Field(None, description="Last error message")
+
+
+class GetStatusResponse(BaseResponse):
+    """Response model for app status."""
+
+    version: str = Field(description="News app version")
+    warnings: dict = Field(default_factory=dict, description="Configuration warnings")

nextcloud_mcp_server/models/semantic.py

@@ -38,6 +38,9 @@ class SemanticSearchResult(BaseModel):
     page_number: Optional[int] = Field(
         default=None, description="Page number for PDF documents"
     )
+    page_count: Optional[int] = Field(
+        default=None, description="Total number of pages in PDF document"
+    )
     # Context expansion fields (optional, populated when include_context=True)
     has_context_expansion: bool = Field(
         default=False, description="Whether context expansion was performed"

nextcloud_mcp_server/observability/logging_config.py

@@ -60,7 +60,7 @@ class TraceContextFormatter(JsonFormatter):
 
     def add_fields(
         self,
-        log_record: dict[str, Any],
+        log_data: dict[str, Any],
         record: logging.LogRecord,
         message_dict: dict[str, Any],
     ) -> None:
@@ -68,28 +68,28 @@ class TraceContextFormatter(JsonFormatter):
         Add custom fields to the log record, including trace context.
 
         Args:
-            log_record: Dictionary to be serialized as JSON
+            log_data: Dictionary to be serialized as JSON
             record: LogRecord instance
             message_dict: Dictionary of extra fields from log call
         """
         # Call parent to add standard fields
-        super().add_fields(log_record, record, message_dict)
+        super().add_fields(log_data, record, message_dict)
 
         # Add trace context if available
         trace_context = get_trace_context()
         if trace_context:
-            log_record["trace_id"] = trace_context.get("trace_id")
+            log_data["trace_id"] = trace_context.get("trace_id")
-            log_record["span_id"] = trace_context.get("span_id")
+            log_data["span_id"] = trace_context.get("span_id")
 
         # Add standard fields with consistent naming
-        log_record["timestamp"] = self.formatTime(record)
+        log_data["timestamp"] = self.formatTime(record)
-        log_record["level"] = record.levelname
+        log_data["level"] = record.levelname
-        log_record["logger"] = record.name
+        log_data["logger"] = record.name
-        log_record["message"] = record.getMessage()
+        log_data["message"] = record.getMessage()
 
         # Include exception info if present
         if record.exc_info:
-            log_record["exception"] = self.formatException(record.exc_info)
+            log_data["exception"] = self.formatException(record.exc_info)
 
 
 class TraceContextTextFormatter(logging.Formatter):

nextcloud_mcp_server/observability/tracing.py

@@ -53,10 +53,11 @@ def setup_tracing(
     global _tracer
 
     # Create resource with service name
+    pkg_name = __package__.split(".")[0] if __package__ else "nextcloud_mcp_server"
     resource = Resource.create(
         {
             "service.name": service_name,
-            "service.version": version(__package__.split(".")[0]),
+            "service.version": version(pkg_name),
         }
     )
 

nextcloud_mcp_server/providers/anthropic.py

@@ -17,18 +17,20 @@ class AnthropicProvider(Provider):
     Note: Anthropic doesn't provide embedding models, only text generation.
     """
 
-    def __init__(self, api_key: str, model: str = "claude-3-5-sonnet-20241022"):
+    def __init__(
+        self, api_key: str, generation_model: str = "claude-3-5-sonnet-20241022"
+    ):
         """
         Initialize Anthropic provider.
 
         Args:
             api_key: Anthropic API key
-            model: Model name (e.g., "claude-3-5-sonnet-20241022")
+            generation_model: Model name (e.g., "claude-3-5-sonnet-20241022")
         """
         self.client = AsyncAnthropic(api_key=api_key)
-        self.model = model
+        self.model = generation_model
 
-        logger.info(f"Initialized Anthropic provider (model={model})")
+        logger.info(f"Initialized Anthropic provider (model={self.model})")
 
     @property
     def supports_embeddings(self) -> bool:

nextcloud_mcp_server/providers/openai.py

@@ -7,13 +7,48 @@ Supports:
 """
 
 import logging
+from functools import wraps
 
-from openai import AsyncOpenAI
+import anyio
+from openai import AsyncOpenAI, RateLimitError
 
 from .base import Provider
 
 logger = logging.getLogger(__name__)
 
+# Rate limit retry configuration
+MAX_RETRIES = 5
+INITIAL_RETRY_DELAY = 2.0  # seconds
+MAX_RETRY_DELAY = 60.0  # seconds
+
+
+def retry_on_rate_limit(func):
+    """Decorator to retry on OpenAI rate limit errors with exponential backoff."""
+
+    @wraps(func)
+    async def wrapper(*args, **kwargs):
+        retry_delay = INITIAL_RETRY_DELAY
+        last_error: Exception | None = None
+
+        for attempt in range(1, MAX_RETRIES + 1):
+            try:
+                return await func(*args, **kwargs)
+            except RateLimitError as e:
+                last_error = e
+                if attempt < MAX_RETRIES:
+                    logger.warning(
+                        f"Rate limit hit (attempt {attempt}/{MAX_RETRIES}), "
+                        f"retrying in {retry_delay:.1f}s..."
+                    )
+                    await anyio.sleep(retry_delay)
+                    retry_delay = min(retry_delay * 2, MAX_RETRY_DELAY)
+
+        logger.error(f"Rate limit exceeded after {MAX_RETRIES} attempts")
+        raise last_error  # type: ignore[misc]
+
+    return wrapper
+
+
 # Well-known embedding dimensions for OpenAI models
 OPENAI_EMBEDDING_DIMENSIONS: dict[str, int] = {
     "text-embedding-3-small": 1536,
@@ -86,6 +121,7 @@ class OpenAIProvider(Provider):
         """Whether this provider supports text generation."""
         return self.generation_model is not None
 
+    @retry_on_rate_limit
     async def embed(self, text: str) -> list[float]:
         """
         Generate embedding vector for text.
@@ -104,6 +140,7 @@ class OpenAIProvider(Provider):
                 "Embedding not supported - no embedding_model configured"
             )
 
+        assert self.embedding_model is not None  # Type narrowing
         response = await self.client.embeddings.create(
             input=text,
             model=self.embedding_model,
@@ -151,14 +188,8 @@ class OpenAIProvider(Provider):
         for i in range(0, len(texts), batch_size):
             batch = texts[i : i + batch_size]
 
-            response = await self.client.embeddings.create(
+            # Use helper method with retry logic for each batch
-                input=batch,
+            batch_embeddings = await self._embed_batch_request(batch)
-                model=self.embedding_model,
-            )
-
-            # Sort by index to maintain order
-            sorted_data = sorted(response.data, key=lambda x: x.index)
-            batch_embeddings = [item.embedding for item in sorted_data]
             all_embeddings.extend(batch_embeddings)
 
             # Update dimension if not set
@@ -171,6 +202,18 @@ class OpenAIProvider(Provider):
 
         return all_embeddings
 
+    @retry_on_rate_limit
+    async def _embed_batch_request(self, batch: list[str]) -> list[list[float]]:
+        """Make a single batch embedding request with retry logic."""
+        assert self.embedding_model is not None  # Type narrowing
+        response = await self.client.embeddings.create(
+            input=batch,
+            model=self.embedding_model,
+        )
+        # Sort by index to maintain order
+        sorted_data = sorted(response.data, key=lambda x: x.index)
+        return [item.embedding for item in sorted_data]
+
     def get_dimension(self) -> int:
         """
         Get embedding dimension.
@@ -194,6 +237,7 @@ class OpenAIProvider(Provider):
             )
         return self._dimension
 
+    @retry_on_rate_limit
     async def generate(self, prompt: str, max_tokens: int = 500) -> str:
         """
         Generate text from a prompt.

nextcloud_mcp_server/search/algorithms.py

@@ -108,10 +108,10 @@ async def get_indexed_doc_types(user_id: str) -> set[str]:
             with_vectors=False,  # Don't need vectors for type discovery
         )
 
-        doc_types = {
+        doc_types: set[str] = {
-            point.payload.get("doc_type")
+            str(point.payload.get("doc_type"))
             for point in scroll_results
-            if point.payload.get("doc_type")
+            if point.payload and point.payload.get("doc_type")
         }
 
         logger.debug(f"Found indexed document types for user {user_id}: {doc_types}")
@@ -138,6 +138,7 @@ class SearchResult:
         chunk_start_offset: Character position where chunk starts (None if not available)
         chunk_end_offset: Character position where chunk ends (None if not available)
         page_number: Page number for PDF documents (None for other doc types)
+        page_count: Total number of pages in PDF document (None for other doc types)
         chunk_index: Zero-based index of this chunk in the document
         total_chunks: Total number of chunks in the document
         point_id: Qdrant point ID for batch vector retrieval (None if not from Qdrant)
@@ -152,6 +153,7 @@ class SearchResult:
     chunk_start_offset: int | None = None
     chunk_end_offset: int | None = None
     page_number: int | None = None
+    page_count: int | None = None
     chunk_index: int = 0
     total_chunks: int = 1
     point_id: str | None = None

nextcloud_mcp_server/search/bm25_hybrid.py

@@ -204,6 +204,8 @@ class BM25HybridSearchAlgorithm(SearchAlgorithm):
             results = []
 
             for result in search_response.points:
+                if result.payload is None:
+                    continue
                 # doc_id can be int (notes) or str (files - file paths)
                 doc_id = result.payload["doc_id"]
                 doc_type = result.payload.get("doc_type", "note")
@@ -217,6 +219,22 @@ class BM25HybridSearchAlgorithm(SearchAlgorithm):
 
                 seen_chunks.add(chunk_key)
 
+                # Build metadata dict with common fields
+                metadata = {
+                    "chunk_index": result.payload.get("chunk_index"),
+                    "total_chunks": result.payload.get("total_chunks"),
+                    "search_method": f"bm25_hybrid_{self.fusion_name}",
+                }
+
+                # Add file-specific metadata for PDF viewer
+                if doc_type == "file" and (path := result.payload.get("file_path")):
+                    metadata["path"] = path
+
+                # Add deck_card-specific metadata for frontend URL construction
+                if doc_type == "deck_card":
+                    if board_id := result.payload.get("board_id"):
+                        metadata["board_id"] = board_id
+
                 # Return unverified results (verification happens at output stage)
                 results.append(
                     SearchResult(
@@ -225,14 +243,11 @@ class BM25HybridSearchAlgorithm(SearchAlgorithm):
                         title=result.payload.get("title", "Untitled"),
                         excerpt=result.payload.get("excerpt", ""),
                         score=result.score,  # Fusion score (RRF or DBSF)
-                        metadata={
+                        metadata=metadata,
-                            "chunk_index": result.payload.get("chunk_index"),
-                            "total_chunks": result.payload.get("total_chunks"),
-                            "search_method": f"bm25_hybrid_{self.fusion_name}",
-                        },
                         chunk_start_offset=result.payload.get("chunk_start_offset"),
                         chunk_end_offset=result.payload.get("chunk_end_offset"),
                         page_number=result.payload.get("page_number"),
+                        page_count=result.payload.get("page_count"),
                         chunk_index=result.payload.get("chunk_index", 0),
                         total_chunks=result.payload.get("total_chunks", 1),
                         point_id=str(result.id),  # Qdrant point ID for batch retrieval

nextcloud_mcp_server/search/context.py

@@ -209,6 +209,64 @@ async def _get_file_path_from_qdrant(
         return None
 
 
+async def _get_deck_metadata_from_qdrant(
+    user_id: str, card_id: int
+) -> dict[str, int] | None:
+    """Retrieve board_id and stack_id for a deck card from Qdrant payload.
+
+    Args:
+        user_id: User ID who owns the card
+        card_id: Card ID
+
+    Returns:
+        Dictionary with board_id and stack_id, or None if not found
+    """
+    try:
+        from qdrant_client.models import FieldCondition, Filter, MatchValue
+
+        from nextcloud_mcp_server.config import get_settings
+        from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
+
+        qdrant_client = await get_qdrant_client()
+        settings = get_settings()
+
+        # Query for any chunk of this card (we just need metadata)
+        scroll_result = await qdrant_client.scroll(
+            collection_name=settings.get_collection_name(),
+            scroll_filter=Filter(
+                must=[
+                    FieldCondition(key="user_id", match=MatchValue(value=user_id)),
+                    FieldCondition(key="doc_id", match=MatchValue(value=card_id)),
+                    FieldCondition(key="doc_type", match=MatchValue(value="deck_card")),
+                ]
+            ),
+            limit=1,
+            with_payload=["board_id", "stack_id"],
+            with_vectors=False,
+        )
+
+        if scroll_result[0]:
+            point = scroll_result[0][0]
+            board_id = point.payload.get("board_id")
+            stack_id = point.payload.get("stack_id")
+            if board_id is not None and stack_id is not None:
+                logger.debug(
+                    f"Retrieved deck metadata for card {card_id}: "
+                    f"board_id={board_id}, stack_id={stack_id}"
+                )
+                return {"board_id": int(board_id), "stack_id": int(stack_id)}
+
+        logger.debug(
+            f"Could not find deck metadata in Qdrant for card {card_id} "
+            f"(might be legacy data without board_id/stack_id)"
+        )
+        return None
+
+    except Exception as e:
+        logger.debug(f"Error querying Qdrant for deck metadata: {e}")
+        return None
+
+
 @dataclass
 class ChunkContext:
     """Expanded chunk with surrounding context and position markers.
@@ -394,7 +452,9 @@ async def get_chunk_with_context(
         logger.debug(f"Resolved file_id {doc_id} to file_path {file_path}")
 
     # Fetch full document text
-    full_text = await _fetch_document_text(nc_client, resolved_doc_id, doc_type)
+    full_text = await _fetch_document_text(
+        nc_client, resolved_doc_id, doc_type, user_id
+    )
     if full_text is None:
         logger.warning(
             f"Could not fetch document text for {doc_type} {doc_id}, "
@@ -453,7 +513,7 @@ async def get_chunk_with_context(
 
 
 async def _fetch_document_text(
-    nc_client: NextcloudClient, doc_id: str | int, doc_type: str
+    nc_client: NextcloudClient, doc_id: str | int, doc_type: str, user_id: str
 ) -> str | None:
     """Fetch full text content of a document.
 
@@ -524,6 +584,96 @@ async def _fetch_document_text(
                     f"Error fetching file content for {doc_id}: {e}", exc_info=True
                 )
                 return None
+        elif doc_type == "news_item":
+            # Fetch news item by ID
+            from nextcloud_mcp_server.vector.html_processor import html_to_markdown
+
+            item = await nc_client.news.get_item(int(doc_id))
+            # Reconstruct full content as indexed: title + source + URL + body
+            # This ensures chunk offsets align with indexed content structure
+            body_markdown = html_to_markdown(item.get("body", ""))
+            item_title = item.get("title", "")
+            item_url = item.get("url", "")
+            feed_title = item.get("feedTitle", "")
+
+            content_parts = [item_title]
+            if feed_title:
+                content_parts.append(f"Source: {feed_title}")
+            if item_url:
+                content_parts.append(f"URL: {item_url}")
+            content_parts.append("")  # Blank line
+            content_parts.append(body_markdown)
+            return "\n".join(content_parts)
+        elif doc_type == "deck_card":
+            # Fetch card from Deck API
+            # Try to get board_id/stack_id from Qdrant metadata (O(1) lookup)
+            # Otherwise fall back to iteration (legacy data)
+            card = None
+            deck_metadata = await _get_deck_metadata_from_qdrant(user_id, int(doc_id))
+
+            if deck_metadata:
+                # Fast path: Direct lookup with known board_id/stack_id
+                board_id = deck_metadata["board_id"]
+                stack_id = deck_metadata["stack_id"]
+                try:
+                    card = await nc_client.deck.get_card(
+                        board_id=board_id, stack_id=stack_id, card_id=int(doc_id)
+                    )
+                    logger.debug(
+                        f"Retrieved deck card {doc_id} using metadata "
+                        f"(board_id={board_id}, stack_id={stack_id})"
+                    )
+                except Exception as e:
+                    logger.warning(
+                        f"Failed to fetch card with metadata (board_id={board_id}, "
+                        f"stack_id={stack_id}, card_id={doc_id}): {e}, falling back to iteration"
+                    )
+
+            # Fallback: Iterate through all boards/stacks (for legacy data or if fast path failed)
+            if card is None:
+                boards = await nc_client.deck.get_boards()
+                card_found = False
+
+                for board in boards:
+                    if card_found:
+                        break
+
+                    # Skip deleted boards (soft delete: deletedAt > 0)
+                    if board.deletedAt > 0:
+                        logger.debug(
+                            f"Skipping deleted board {board.id} while searching for card {doc_id}"
+                        )
+                        continue
+
+                    stacks = await nc_client.deck.get_stacks(board.id)
+
+                    for stack in stacks:
+                        if card_found:
+                            break
+                        if stack.cards:
+                            for c in stack.cards:
+                                if c.id == int(doc_id):
+                                    card = c
+                                    card_found = True
+                                    logger.debug(
+                                        f"Found deck card {doc_id} in board {board.id}, "
+                                        f"stack {stack.id} (fallback iteration)"
+                                    )
+                                    break
+
+                if not card_found:
+                    logger.warning(f"Deck card {doc_id} not found in any board/stack")
+                    return None
+
+            # Type narrowing: card is set if we reach here
+            assert card is not None
+
+            # Reconstruct full content as indexed: title + "\n\n" + description
+            # This ensures chunk offsets align with indexed content structure
+            content_parts = [card.title]
+            if card.description:
+                content_parts.append(card.description)
+            return "\n\n".join(content_parts)
         else:
             logger.warning(f"Unsupported doc_type for context expansion: {doc_type}")
             return None

nextcloud_mcp_server/search/semantic.py

@@ -136,6 +136,8 @@ class SemanticSearchAlgorithm(SearchAlgorithm):
         results = []
 
         for result in search_response.points:
+            if result.payload is None:
+                continue
             # doc_id can be int (notes) or str (files - file paths)
             doc_id = result.payload["doc_id"]
             doc_type = result.payload.get("doc_type", "note")
@@ -149,6 +151,21 @@ class SemanticSearchAlgorithm(SearchAlgorithm):
 
             seen_chunks.add(chunk_key)
 
+            # Build metadata dict with common fields
+            metadata = {
+                "chunk_index": result.payload.get("chunk_index"),
+                "total_chunks": result.payload.get("total_chunks"),
+            }
+
+            # Add file-specific metadata for PDF viewer
+            if doc_type == "file" and (path := result.payload.get("file_path")):
+                metadata["path"] = path
+
+            # Add deck_card-specific metadata for frontend URL construction
+            if doc_type == "deck_card":
+                if board_id := result.payload.get("board_id"):
+                    metadata["board_id"] = board_id
+
             # Return unverified results (verification happens at output stage)
             results.append(
                 SearchResult(
@@ -157,13 +174,11 @@ class SemanticSearchAlgorithm(SearchAlgorithm):
                     title=result.payload.get("title", "Untitled"),
                     excerpt=result.payload.get("excerpt", ""),
                     score=result.score,
-                    metadata={
+                    metadata=metadata,
-                        "chunk_index": result.payload.get("chunk_index"),
-                        "total_chunks": result.payload.get("total_chunks"),
-                    },
                     chunk_start_offset=result.payload.get("chunk_start_offset"),
                     chunk_end_offset=result.payload.get("chunk_end_offset"),
                     page_number=result.payload.get("page_number"),
+                    page_count=result.payload.get("page_count"),
                     chunk_index=result.payload.get("chunk_index", 0),
                     total_chunks=result.payload.get("total_chunks", 1),
                     point_id=str(result.id),  # Qdrant point ID for batch retrieval

nextcloud_mcp_server/server/__init__.py

@@ -2,6 +2,7 @@ from .calendar import configure_calendar_tools
 from .contacts import configure_contacts_tools
 from .cookbook import configure_cookbook_tools
 from .deck import configure_deck_tools
+from .news import configure_news_tools
 from .notes import configure_notes_tools
 from .semantic import configure_semantic_tools
 from .sharing import configure_sharing_tools
@@ -13,6 +14,7 @@ __all__ = [
     "configure_contacts_tools",
     "configure_cookbook_tools",
     "configure_deck_tools",
+    "configure_news_tools",
     "configure_notes_tools",
     "configure_semantic_tools",
     "configure_sharing_tools",

nextcloud_mcp_server/server/calendar.py

@@ -3,6 +3,7 @@ import logging
 from typing import Optional
 
 from mcp.server.fastmcp import Context, FastMCP
+from mcp.types import ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -19,7 +20,10 @@ logger = logging.getLogger(__name__)
 
 def configure_calendar_tools(mcp: FastMCP):
     # Calendar tools
-    @mcp.tool()
+    @mcp.tool(
+        title="List Calendars",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("calendar:read")
     @instrument_tool
     async def nc_calendar_list_calendars(ctx: Context) -> ListCalendarsResponse:
@@ -30,7 +34,10 @@ def configure_calendar_tools(mcp: FastMCP):
         calendars = [Calendar(**cal_data) for cal_data in calendars_data]
         return ListCalendarsResponse(calendars=calendars, total_count=len(calendars))
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Calendar Event",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("calendar:write")
     @instrument_tool
     async def nc_calendar_create_event(
@@ -107,7 +114,10 @@ def configure_calendar_tools(mcp: FastMCP):
 
         return await client.calendar.create_event(calendar_name, event_data)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Calendar Events",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("calendar:read")
     @instrument_tool
     async def nc_calendar_list_events(
@@ -210,7 +220,10 @@ def configure_calendar_tools(mcp: FastMCP):
 
             return events
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Calendar Event",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("calendar:read")
     @instrument_tool
     async def nc_calendar_get_event(
@@ -223,7 +236,10 @@ def configure_calendar_tools(mcp: FastMCP):
         event_data, etag = await client.calendar.get_event(calendar_name, event_uid)
         return event_data
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Calendar Event",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("calendar:write")
     @instrument_tool
     async def nc_calendar_update_event(
@@ -297,7 +313,12 @@ def configure_calendar_tools(mcp: FastMCP):
             calendar_name, event_uid, event_data, etag
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Calendar Event",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("calendar:write")
     @instrument_tool
     async def nc_calendar_delete_event(
@@ -309,7 +330,10 @@ def configure_calendar_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.calendar.delete_event(calendar_name, event_uid)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Meeting",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("calendar:write")
     @instrument_tool
     async def nc_calendar_create_meeting(
@@ -376,7 +400,10 @@ def configure_calendar_tools(mcp: FastMCP):
 
         return await client.calendar.create_event(calendar_name, event_data)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Upcoming Events",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("calendar:read")
     @instrument_tool
     async def nc_calendar_get_upcoming_events(
@@ -427,7 +454,10 @@ def configure_calendar_tools(mcp: FastMCP):
             all_events.sort(key=lambda x: x.get("start_datetime", ""))
             return all_events[:limit]
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Find Availability",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("calendar:read")
     @instrument_tool
     async def nc_calendar_find_availability(
@@ -508,7 +538,10 @@ def configure_calendar_tools(mcp: FastMCP):
             constraints=constraints,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Bulk Calendar Operations",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("calendar:write")
     @instrument_tool
     async def nc_calendar_bulk_operations(
@@ -758,7 +791,10 @@ def configure_calendar_tools(mcp: FastMCP):
                 "results": results,
             }
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Manage Calendar",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("calendar:write")
     @instrument_tool
     async def nc_calendar_manage_calendar(
@@ -828,7 +864,10 @@ def configure_calendar_tools(mcp: FastMCP):
 
     # ============= Todo/Task Tools =============
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Todo Tasks",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("todo:read", "calendar:read")
     @instrument_tool
     async def nc_calendar_list_todos(
@@ -874,7 +913,10 @@ def configure_calendar_tools(mcp: FastMCP):
             todos=todos, calendar_name=calendar_name, total_count=len(todos)
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Todo Task",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("todo:write", "calendar:read")
     @instrument_tool
     async def nc_calendar_create_todo(
@@ -918,7 +960,10 @@ def configure_calendar_tools(mcp: FastMCP):
 
         return await client.calendar.create_todo(calendar_name, todo_data)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Todo Task",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("todo:write", "calendar:read")
     @instrument_tool
     async def nc_calendar_update_todo(
@@ -979,7 +1024,12 @@ def configure_calendar_tools(mcp: FastMCP):
 
         return await client.calendar.update_todo(calendar_name, todo_uid, todo_data)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Todo Task",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("todo:write", "calendar:read")
     @instrument_tool
     async def nc_calendar_delete_todo(
@@ -1000,7 +1050,10 @@ def configure_calendar_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.calendar.delete_todo(calendar_name, todo_uid)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Search Todo Tasks",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("todo:read", "calendar:read")
     @instrument_tool
     async def nc_calendar_search_todos(

nextcloud_mcp_server/server/contacts.py

@@ -1,6 +1,7 @@
 import logging
 
 from mcp.server.fastmcp import Context, FastMCP
+from mcp.types import ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -11,7 +12,10 @@ logger = logging.getLogger(__name__)
 
 def configure_contacts_tools(mcp: FastMCP):
     # Contacts tools
-    @mcp.tool()
+    @mcp.tool(
+        title="List Address Books",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("contacts:read")
     @instrument_tool
     async def nc_contacts_list_addressbooks(ctx: Context):
@@ -19,7 +23,10 @@ def configure_contacts_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.contacts.list_addressbooks()
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Contacts",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("contacts:read")
     @instrument_tool
     async def nc_contacts_list_contacts(ctx: Context, *, addressbook: str):
@@ -27,7 +34,10 @@ def configure_contacts_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.contacts.list_contacts(addressbook=addressbook)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Address Book",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("contacts:write")
     @instrument_tool
     async def nc_contacts_create_addressbook(
@@ -44,7 +54,12 @@ def configure_contacts_tools(mcp: FastMCP):
             name=name, display_name=display_name
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Address Book",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("contacts:write")
     @instrument_tool
     async def nc_contacts_delete_addressbook(ctx: Context, *, name: str):
@@ -52,7 +67,10 @@ def configure_contacts_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.contacts.delete_addressbook(name=name)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Contact",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("contacts:write")
     @instrument_tool
     async def nc_contacts_create_contact(
@@ -70,7 +88,12 @@ def configure_contacts_tools(mcp: FastMCP):
             addressbook=addressbook, uid=uid, contact_data=contact_data
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Contact",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("contacts:write")
     @instrument_tool
     async def nc_contacts_delete_contact(ctx: Context, *, addressbook: str, uid: str):
@@ -78,7 +101,10 @@ def configure_contacts_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.contacts.delete_contact(addressbook=addressbook, uid=uid)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Contact",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("contacts:write")
     @instrument_tool
     async def nc_contacts_update_contact(

nextcloud_mcp_server/server/cookbook.py

@@ -3,7 +3,7 @@ import logging
 from httpx import HTTPStatusError, RequestError
 from mcp.server.fastmcp import Context, FastMCP
 from mcp.shared.exceptions import McpError
-from mcp.types import ErrorData
+from mcp.types import ErrorData, ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -71,7 +71,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Import Recipe from URL",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("cookbook:write")
     @instrument_tool
     async def nc_cookbook_import_recipe(url: str, ctx: Context) -> ImportRecipeResponse:
@@ -129,7 +132,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Recipes",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("cookbook:read")
     @instrument_tool
     async def nc_cookbook_list_recipes(ctx: Context) -> ListRecipesResponse:
@@ -155,7 +161,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Recipe",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("cookbook:read")
     @instrument_tool
     async def nc_cookbook_get_recipe(recipe_id: int, ctx: Context) -> Recipe:
@@ -181,7 +190,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Recipe",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("cookbook:write")
     @instrument_tool
     async def nc_cookbook_create_recipe(
@@ -261,7 +273,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Recipe",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("cookbook:write")
     @instrument_tool
     async def nc_cookbook_update_recipe(
@@ -351,7 +366,12 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Recipe",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("cookbook:write")
     @instrument_tool
     async def nc_cookbook_delete_recipe(
@@ -387,7 +407,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Search Recipes",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("cookbook:read")
     @instrument_tool
     async def nc_cookbook_search_recipes(
@@ -424,7 +447,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Recipe Categories",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("cookbook:read")
     @instrument_tool
     async def nc_cookbook_list_categories(ctx: Context) -> ListCategoriesResponse:
@@ -452,7 +478,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Recipes in Category",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("cookbook:read")
     @instrument_tool
     async def nc_cookbook_get_recipes_in_category(
@@ -489,7 +518,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Recipe Keywords",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("cookbook:read")
     @instrument_tool
     async def nc_cookbook_list_keywords(ctx: Context) -> ListKeywordsResponse:
@@ -515,7 +547,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Recipes with Keywords",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("cookbook:read")
     @instrument_tool
     async def nc_cookbook_get_recipes_with_keywords(
@@ -550,7 +585,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Set Cookbook Configuration",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("cookbook:write")
     @instrument_tool
     async def nc_cookbook_set_config(
@@ -594,7 +632,10 @@ def configure_cookbook_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Reindex Recipes",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("cookbook:write")
     @instrument_tool
     async def nc_cookbook_reindex(ctx: Context) -> ReindexResponse:

nextcloud_mcp_server/server/deck.py

@@ -2,6 +2,7 @@ import logging
 from typing import Optional
 
 from mcp.server.fastmcp import Context, FastMCP
+from mcp.types import ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -117,7 +118,10 @@ def configure_deck_tools(mcp: FastMCP):
 
     # Read Tools (converted from resources)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Deck Boards",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_boards(ctx: Context) -> list[DeckBoard]:
@@ -126,7 +130,10 @@ def configure_deck_tools(mcp: FastMCP):
         boards = await client.deck.get_boards()
         return boards
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Deck Board",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_board(ctx: Context, board_id: int) -> DeckBoard:
@@ -135,7 +142,10 @@ def configure_deck_tools(mcp: FastMCP):
         board = await client.deck.get_board(board_id)
         return board
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Deck Stacks",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_stacks(ctx: Context, board_id: int) -> list[DeckStack]:
@@ -144,7 +154,10 @@ def configure_deck_tools(mcp: FastMCP):
         stacks = await client.deck.get_stacks(board_id)
         return stacks
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Deck Stack",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_stack(ctx: Context, board_id: int, stack_id: int) -> DeckStack:
@@ -153,7 +166,10 @@ def configure_deck_tools(mcp: FastMCP):
         stack = await client.deck.get_stack(board_id, stack_id)
         return stack
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Deck Cards",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_cards(
@@ -166,7 +182,10 @@ def configure_deck_tools(mcp: FastMCP):
             return stack.cards
         return []
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Deck Card",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_card(
@@ -177,7 +196,10 @@ def configure_deck_tools(mcp: FastMCP):
         card = await client.deck.get_card(board_id, stack_id, card_id)
         return card
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Deck Labels",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_labels(ctx: Context, board_id: int) -> list[DeckLabel]:
@@ -186,7 +208,10 @@ def configure_deck_tools(mcp: FastMCP):
         board = await client.deck.get_board(board_id)
         return board.labels
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Deck Label",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("deck:read")
     @instrument_tool
     async def deck_get_label(ctx: Context, board_id: int, label_id: int) -> DeckLabel:
@@ -197,7 +222,10 @@ def configure_deck_tools(mcp: FastMCP):
 
     # Create/Update/Delete Tools
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Deck Board",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_create_board(
@@ -215,7 +243,10 @@ def configure_deck_tools(mcp: FastMCP):
 
     # Stack Tools
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Deck Stack",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_create_stack(
@@ -232,7 +263,10 @@ def configure_deck_tools(mcp: FastMCP):
         stack = await client.deck.create_stack(board_id, title, order)
         return CreateStackResponse(id=stack.id, title=stack.title, order=stack.order)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Deck Stack",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_update_stack(
@@ -259,7 +293,12 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Deck Stack",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_delete_stack(
@@ -281,7 +320,10 @@ def configure_deck_tools(mcp: FastMCP):
         )
 
     # Card Tools
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_create_card(
@@ -316,7 +358,10 @@ def configure_deck_tools(mcp: FastMCP):
             stackId=card.stackId,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_update_card(
@@ -370,7 +415,12 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Deck Card",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_delete_card(
@@ -393,7 +443,10 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Archive Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_archive_card(
@@ -416,7 +469,10 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Unarchive Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_unarchive_card(
@@ -439,7 +495,10 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Reorder/Move Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_reorder_card(
@@ -472,7 +531,10 @@ def configure_deck_tools(mcp: FastMCP):
         )
 
     # Label Tools
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Deck Label",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_create_label(
@@ -489,7 +551,10 @@ def configure_deck_tools(mcp: FastMCP):
         label = await client.deck.create_label(board_id, title, color)
         return CreateLabelResponse(id=label.id, title=label.title, color=label.color)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Deck Label",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_update_label(
@@ -516,7 +581,12 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Deck Label",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_delete_label(
@@ -538,7 +608,10 @@ def configure_deck_tools(mcp: FastMCP):
         )
 
     # Card-Label Assignment Tools
-    @mcp.tool()
+    @mcp.tool(
+        title="Assign Label to Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_assign_label_to_card(
@@ -562,7 +635,10 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Remove Label from Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_remove_label_from_card(
@@ -587,7 +663,10 @@ def configure_deck_tools(mcp: FastMCP):
         )
 
     # Card-User Assignment Tools
-    @mcp.tool()
+    @mcp.tool(
+        title="Assign User to Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_assign_user_to_card(
@@ -611,7 +690,10 @@ def configure_deck_tools(mcp: FastMCP):
             board_id=board_id,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Unassign User from Deck Card",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("deck:write")
     @instrument_tool
     async def deck_unassign_user_from_card(

nextcloud_mcp_server/server/news.py

@@ -0,0 +1,384 @@
+"""MCP tools for Nextcloud News app."""
+
+import logging
+
+from httpx import HTTPStatusError, RequestError
+from mcp.server.fastmcp import Context, FastMCP
+from mcp.shared.exceptions import McpError
+from mcp.types import ErrorData, ToolAnnotations
+
+from nextcloud_mcp_server.auth import require_scopes
+from nextcloud_mcp_server.client.news import NewsItemType
+from nextcloud_mcp_server.context import get_client
+from nextcloud_mcp_server.models.news import (
+    FeedHealthResponse,
+    GetItemResponse,
+    GetStatusResponse,
+    ListFeedsResponse,
+    ListFoldersResponse,
+    ListItemsResponse,
+    NewsFeed,
+    NewsFolder,
+    NewsItem,
+    NewsItemSummary,
+)
+from nextcloud_mcp_server.observability.metrics import instrument_tool
+
+logger = logging.getLogger(__name__)
+
+
+def configure_news_tools(mcp: FastMCP):
+    """Configure News app MCP tools."""
+
+    @mcp.tool(
+        title="List News Folders",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_list_folders(ctx: Context) -> ListFoldersResponse:
+        """List all News folders (requires news:read scope)."""
+        client = await get_client(ctx)
+        try:
+            folders_data = await client.news.get_folders()
+            folders = [NewsFolder(**f) for f in folders_data]
+            return ListFoldersResponse(results=folders, total_count=len(folders))
+        except RequestError as e:
+            raise McpError(
+                ErrorData(code=-1, message=f"Network error listing folders: {str(e)}")
+            )
+        except HTTPStatusError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to list folders: {e.response.status_code}",
+                )
+            )
+
+    @mcp.tool(
+        title="List News Feeds",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_list_feeds(ctx: Context) -> ListFeedsResponse:
+        """List all News feeds with metadata (requires news:read scope).
+
+        Returns feeds with unread counts, error status, and overall starred count.
+        """
+        client = await get_client(ctx)
+        try:
+            data = await client.news.get_feeds()
+            feeds = [NewsFeed(**f) for f in data.get("feeds", [])]
+            return ListFeedsResponse(
+                results=feeds,
+                starred_count=data.get("starredCount", 0),
+                newest_item_id=data.get("newestItemId"),
+                total_count=len(feeds),
+            )
+        except RequestError as e:
+            raise McpError(
+                ErrorData(code=-1, message=f"Network error listing feeds: {str(e)}")
+            )
+        except HTTPStatusError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to list feeds: {e.response.status_code}",
+                )
+            )
+
+    @mcp.tool(
+        title="List News Items",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_list_items(
+        ctx: Context,
+        feed_id: int | None = None,
+        folder_id: int | None = None,
+        starred_only: bool = False,
+        unread_only: bool = False,
+        limit: int = 50,
+        offset: int = 0,
+    ) -> ListItemsResponse:
+        """List News items (articles) with optional filtering (requires news:read scope).
+
+        Args:
+            feed_id: Filter by specific feed ID
+            folder_id: Filter by specific folder ID
+            starred_only: Return only starred items
+            unread_only: Return only unread items
+            limit: Maximum number of items to return (default 50, -1 for all)
+            offset: Item ID to start after (for pagination)
+
+        Returns:
+            ListItemsResponse with items, count, and pagination info
+        """
+        client = await get_client(ctx)
+
+        # Determine item type filter
+        type_ = NewsItemType.ALL
+        id_ = 0
+        if starred_only:
+            type_ = NewsItemType.STARRED
+        elif feed_id is not None:
+            type_ = NewsItemType.FEED
+            id_ = feed_id
+        elif folder_id is not None:
+            type_ = NewsItemType.FOLDER
+            id_ = folder_id
+
+        try:
+            items_data = await client.news.get_items(
+                batch_size=limit,
+                offset=offset,
+                type_=type_,
+                id_=id_,
+                get_read=not unread_only,
+            )
+            items = [NewsItemSummary(**i) for i in items_data]
+
+            # Determine pagination info
+            oldest_id = min((i.id for i in items), default=None) if items else None
+            has_more = len(items) == limit and limit > 0
+
+            return ListItemsResponse(
+                results=items,
+                total_count=len(items),
+                has_more=has_more,
+                oldest_id=oldest_id,
+            )
+        except RequestError as e:
+            raise McpError(
+                ErrorData(code=-1, message=f"Network error listing items: {str(e)}")
+            )
+        except HTTPStatusError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to list items: {e.response.status_code}",
+                )
+            )
+
+    @mcp.tool(
+        title="Get News Item",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_get_item(item_id: int, ctx: Context) -> GetItemResponse:
+        """Get a specific News item by ID with full content (requires news:read scope).
+
+        Args:
+            item_id: Item ID
+
+        Returns:
+            GetItemResponse with full item details including HTML body
+        """
+        client = await get_client(ctx)
+        try:
+            item_data = await client.news.get_item(item_id)
+            item = NewsItem(**item_data)
+            return GetItemResponse(item=item)
+        except ValueError as e:
+            raise McpError(ErrorData(code=-1, message=str(e)))
+        except RequestError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1, message=f"Network error getting item {item_id}: {str(e)}"
+                )
+            )
+        except HTTPStatusError as e:
+            if e.response.status_code == 404:
+                raise McpError(ErrorData(code=-1, message=f"Item {item_id} not found"))
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to get item {item_id}: {e.response.status_code}",
+                )
+            )
+
+    @mcp.tool(
+        title="Get Starred News Items",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_get_starred_items(
+        ctx: Context, limit: int = 50, offset: int = 0
+    ) -> ListItemsResponse:
+        """Get starred (favorited) News items (requires news:read scope).
+
+        Convenience method for retrieving user's starred articles.
+
+        Args:
+            limit: Maximum number of items to return (default 50, -1 for all)
+            offset: Item ID to start after (for pagination)
+
+        Returns:
+            ListItemsResponse with starred items
+        """
+        client = await get_client(ctx)
+        try:
+            items_data = await client.news.get_items(
+                batch_size=limit,
+                offset=offset,
+                type_=NewsItemType.STARRED,
+                get_read=True,  # Include read starred items
+            )
+            items = [NewsItemSummary(**i) for i in items_data]
+
+            oldest_id = min((i.id for i in items), default=None) if items else None
+            has_more = len(items) == limit and limit > 0
+
+            return ListItemsResponse(
+                results=items,
+                total_count=len(items),
+                has_more=has_more,
+                oldest_id=oldest_id,
+            )
+        except RequestError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1, message=f"Network error getting starred items: {str(e)}"
+                )
+            )
+        except HTTPStatusError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to get starred items: {e.response.status_code}",
+                )
+            )
+
+    @mcp.tool(
+        title="Get Unread News Items",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_get_unread_items(
+        ctx: Context, limit: int = 50, offset: int = 0
+    ) -> ListItemsResponse:
+        """Get unread News items (requires news:read scope).
+
+        Convenience method for retrieving unread articles across all feeds.
+
+        Args:
+            limit: Maximum number of items to return (default 50, -1 for all)
+            offset: Item ID to start after (for pagination)
+
+        Returns:
+            ListItemsResponse with unread items
+        """
+        client = await get_client(ctx)
+        try:
+            items_data = await client.news.get_items(
+                batch_size=limit,
+                offset=offset,
+                type_=NewsItemType.ALL,
+                get_read=False,  # Only unread items
+            )
+            items = [NewsItemSummary(**i) for i in items_data]
+
+            oldest_id = min((i.id for i in items), default=None) if items else None
+            has_more = len(items) == limit and limit > 0
+
+            return ListItemsResponse(
+                results=items,
+                total_count=len(items),
+                has_more=has_more,
+                oldest_id=oldest_id,
+            )
+        except RequestError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1, message=f"Network error getting unread items: {str(e)}"
+                )
+            )
+        except HTTPStatusError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to get unread items: {e.response.status_code}",
+                )
+            )
+
+    @mcp.tool(
+        title="Get News Feed Health",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_get_feed_health(feed_id: int, ctx: Context) -> FeedHealthResponse:
+        """Get health status for a specific feed (requires news:read scope).
+
+        Returns error count and last error message if the feed has update issues.
+
+        Args:
+            feed_id: Feed ID to check
+
+        Returns:
+            FeedHealthResponse with error status
+        """
+        client = await get_client(ctx)
+        try:
+            data = await client.news.get_feeds()
+            for feed_data in data.get("feeds", []):
+                if feed_data.get("id") == feed_id:
+                    feed = NewsFeed(**feed_data)
+                    return FeedHealthResponse(
+                        feed_id=feed.id,
+                        title=feed.title,
+                        url=feed.url,
+                        has_errors=feed.has_errors,
+                        error_count=feed.update_error_count,
+                        last_error=feed.last_update_error,
+                    )
+            raise McpError(ErrorData(code=-1, message=f"Feed {feed_id} not found"))
+        except RequestError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Network error getting feed health: {str(e)}",
+                )
+            )
+        except HTTPStatusError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to get feed health: {e.response.status_code}",
+                )
+            )
+
+    @mcp.tool(
+        title="Get News App Status",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
+    @require_scopes("news:read")
+    @instrument_tool
+    async def nc_news_get_status(ctx: Context) -> GetStatusResponse:
+        """Get News app status and version (requires news:read scope).
+
+        Returns version information and any configuration warnings.
+        """
+        client = await get_client(ctx)
+        try:
+            status_data = await client.news.get_status()
+            return GetStatusResponse(
+                version=status_data.get("version", "unknown"),
+                warnings=status_data.get("warnings", {}),
+            )
+        except RequestError as e:
+            raise McpError(
+                ErrorData(code=-1, message=f"Network error getting status: {str(e)}")
+            )
+        except HTTPStatusError as e:
+            raise McpError(
+                ErrorData(
+                    code=-1,
+                    message=f"Failed to get status: {e.response.status_code}",
+                )
+            )

nextcloud_mcp_server/server/notes.py

@@ -3,7 +3,7 @@ import logging
 from httpx import HTTPStatusError, RequestError
 from mcp.server.fastmcp import Context, FastMCP
 from mcp.shared.exceptions import McpError
-from mcp.types import ErrorData
+from mcp.types import ErrorData, ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -85,7 +85,13 @@ def configure_notes_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Note",
+        annotations=ToolAnnotations(
+            idempotentHint=False,  # Multiple calls create multiple notes
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("notes:write")
     @instrument_tool
     async def nc_notes_create_note(
@@ -132,7 +138,13 @@ def configure_notes_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Note",
+        annotations=ToolAnnotations(
+            idempotentHint=False,  # Requires etag which changes = not idempotent
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("notes:write")
     @instrument_tool
     async def nc_notes_update_note(
@@ -198,7 +210,13 @@ def configure_notes_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Append to Note",
+        annotations=ToolAnnotations(
+            idempotentHint=False,  # Each call adds content = not idempotent
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("notes:write")
     @instrument_tool
     async def nc_notes_append_content(
@@ -249,7 +267,13 @@ def configure_notes_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Search Notes",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Search doesn't modify data
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("notes:read")
     @instrument_tool
     async def nc_notes_search_notes(query: str, ctx: Context) -> SearchNotesResponse:
@@ -296,7 +320,13 @@ def configure_notes_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Note",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Read operation only
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("notes:read")
     @instrument_tool
     async def nc_notes_get_note(note_id: int, ctx: Context) -> Note:
@@ -326,7 +356,13 @@ def configure_notes_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Note Attachment",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Read operation only
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("notes:read")
     @instrument_tool
     async def nc_notes_get_attachment(
@@ -373,7 +409,14 @@ def configure_notes_tools(mcp: FastMCP):
                     )
                 )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Note",
+        annotations=ToolAnnotations(
+            destructiveHint=True,  # Permanently deletes data
+            idempotentHint=True,  # Deleting deleted note = same end state
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("notes:write")
     @instrument_tool
     async def nc_notes_delete_note(note_id: int, ctx: Context) -> DeleteNoteResponse:

nextcloud_mcp_server/server/oauth_tools.py

@@ -15,6 +15,7 @@ import httpx
 from mcp.server.auth.middleware.auth_context import get_access_token
 from mcp.server.auth.provider import AccessToken
 from mcp.server.fastmcp import Context
+from mcp.types import ToolAnnotations
 from pydantic import BaseModel, Field
 
 from nextcloud_mcp_server.auth import require_scopes
@@ -100,6 +101,9 @@ class ProvisioningStatus(BaseModel):
     provisioned_at: Optional[str] = Field(
         None, description="ISO timestamp when provisioned"
     )
+    credential_type: Optional[str] = Field(
+        None, description="Type of credential ('refresh_token' or 'app_password')"
+    )
     client_id: Optional[str] = Field(
         None, description="Client ID that initiated the original Flow 1"
     )
@@ -113,8 +117,8 @@ class ProvisioningResult(BaseModel):
     """Result of provisioning attempt."""
 
     success: bool = Field(description="Whether provisioning was initiated")
-    authorization_url: Optional[str] = Field(
+    provisioning_url: Optional[str] = Field(
-        None, description="URL for user to complete OAuth authorization"
+        None, description="URL to Astrolabe settings for provisioning background sync"
     )
     message: str = Field(description="Status message for the user")
     already_provisioned: bool = Field(
@@ -142,8 +146,9 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
     """
     Check the provisioning status for Nextcloud access.
 
-    This checks whether the user has completed Flow 2 to provision
+    Checks for both credential types:
-    offline access to Nextcloud resources.
+    1. App password from Astrolabe (works today)
+    2. OAuth refresh token from storage (for future)
 
     Args:
         mcp: MCP context
@@ -152,6 +157,37 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
     Returns:
         ProvisioningStatus with current provisioning state
     """
+    from datetime import datetime, timezone
+
+    from nextcloud_mcp_server.auth.astrolabe_client import AstrolabeClient
+    from nextcloud_mcp_server.config import get_settings
+
+    settings = get_settings()
+
+    # Check for app password first (interim solution)
+    if settings.oidc_client_id and settings.oidc_client_secret:
+        try:
+            astrolabe = AstrolabeClient(
+                nextcloud_host=settings.nextcloud_host or "",
+                client_id=settings.oidc_client_id,
+                client_secret=settings.oidc_client_secret,
+            )
+            status = await astrolabe.get_background_sync_status(user_id)
+
+            if status.get("has_access"):
+                logger.info(
+                    f"  get_provisioning_status: ✓ App password FOUND for user_id={user_id}"
+                )
+                provisioned_at_str = status.get("provisioned_at")
+                return ProvisioningStatus(
+                    is_provisioned=True,
+                    provisioned_at=provisioned_at_str,
+                    credential_type="app_password",
+                )
+        except Exception as e:
+            logger.debug(f"  App password check failed for {user_id}: {e}")
+
+    # Check for OAuth refresh token (fallback)
     logger.info(
         f"  get_provisioning_status: Looking up refresh token for user_id={user_id}"
     )
@@ -162,7 +198,7 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
 
     if not token_data:
         logger.info(
-            f"  get_provisioning_status: ✗ No refresh token found for user_id={user_id}"
+            f"  get_provisioning_status: ✗ No credentials found for user_id={user_id}"
         )
         return ProvisioningStatus(is_provisioned=False)
 
@@ -177,14 +213,13 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
     # Convert timestamp to ISO format if present
     provisioned_at_str = None
     if token_data.get("provisioned_at"):
-        from datetime import datetime, timezone
-
         dt = datetime.fromtimestamp(token_data["provisioned_at"], tz=timezone.utc)
         provisioned_at_str = dt.isoformat()
 
     return ProvisioningStatus(
         is_provisioned=True,
         provisioned_at=provisioned_at_str,
+        credential_type="refresh_token",
         client_id=token_data.get("provisioning_client_id"),
         scopes=token_data.get("scopes"),
         flow_type=token_data.get("flow_type", "hybrid"),
@@ -238,36 +273,22 @@ async def provision_nextcloud_access(
     """
     MCP Tool: Provision offline access to Nextcloud resources.
 
-    This tool initiates Flow 2 of the Progressive Consent architecture,
+    Returns URL to Astrolabe settings page where users can provision background
-    allowing the MCP server to obtain delegated access to Nextcloud APIs.
+    sync access using either:
-
+    - App password (works today, interim solution)
-    The user must complete the OAuth flow in their browser to grant access.
+    - OAuth refresh token (future, when Nextcloud supports OAuth for app APIs)
 
     Args:
         ctx: MCP context with user's Flow 1 token
         user_id: Optional user identifier (extracted from token if not provided)
 
     Returns:
-        ProvisioningResult with authorization URL or status
+        ProvisioningResult with Astrolabe settings URL or status
     """
     try:
         # Extract user ID from the MCP access token (Flow 1 token)
         if not user_id:
-            # Get the authorization token from context
+            user_id = await extract_user_id_from_token(ctx)
-            if hasattr(ctx, "authorization") and ctx.authorization:
-                token = ctx.authorization.token  # type: ignore
-                # Decode token to get user info
-                try:
-                    import jwt
-
-                    payload = jwt.decode(token, options={"verify_signature": False})
-                    user_id = payload.get("sub", "unknown")
-                    logger.info(f"Extracted user_id from Flow 1 token: {user_id}")
-                except Exception as e:
-                    logger.warning(f"Failed to decode token: {e}")
-                    user_id = "default_user"
-            else:
-                user_id = "default_user"
 
         # Check if already provisioned
         status = await get_provisioning_status(ctx, user_id)
@@ -276,7 +297,8 @@ async def provision_nextcloud_access(
                 success=True,
                 already_provisioned=True,
                 message=(
-                    f"Nextcloud access is already provisioned (since {status.provisioned_at}). "
+                    f"Nextcloud access is already provisioned (credential_type={status.credential_type}, "
+                    f"since {status.provisioned_at}). "
                     "Use 'revoke_nextcloud_access' if you want to re-provision."
                 ),
             )
@@ -294,83 +316,20 @@ async def provision_nextcloud_access(
                 ),
             )
 
-        # Get MCP server's OAuth client credentials
+        # Return Astrolabe settings URL for background sync provisioning
-        # Try environment variable first, then fall back to DCR client_id
+        nextcloud_host = os.getenv("NEXTCLOUD_HOST", "http://localhost:8080")
-        server_client_id = os.getenv("MCP_SERVER_CLIENT_ID")
+        astrolabe_url = f"{nextcloud_host}/settings/user/astrolabe#background-sync"
-        if not server_client_id:
-            # Try to get from lifespan context (DCR)
-            lifespan_ctx = ctx.request_context.lifespan_context
-            if hasattr(lifespan_ctx, "server_client_id"):
-                server_client_id = lifespan_ctx.server_client_id
-
-        if not server_client_id:
-            return ProvisioningResult(
-                success=False,
-                message=(
-                    "MCP server OAuth client not configured. "
-                    "Set MCP_SERVER_CLIENT_ID environment variable or use Dynamic Client Registration."
-                ),
-            )
-
-        # Generate OAuth URL for Flow 2
-        oidc_discovery_url = os.getenv(
-            "OIDC_DISCOVERY_URL",
-            f"{os.getenv('NEXTCLOUD_HOST')}/.well-known/openid-configuration",
-        )
-
-        # Generate secure state for CSRF protection
-        state = secrets.token_urlsafe(32)
-
-        # Store state in session for validation on callback
-        storage = RefreshTokenStorage.from_env()
-        await storage.initialize()
-
-        # Create OAuth session for Flow 2
-        session_id = f"flow2_{user_id}_{secrets.token_hex(8)}"
-        redirect_uri = f"{os.getenv('NEXTCLOUD_MCP_SERVER_URL', 'http://localhost:8000')}/oauth/callback"
-
-        await storage.store_oauth_session(
-            session_id=session_id,
-            client_redirect_uri="",  # No client redirect for Flow 2
-            state=state,
-            flow_type="flow2",
-            is_provisioning=True,
-            ttl_seconds=600,  # 10 minute TTL
-        )
-
-        # Define scopes for Nextcloud access
-        scopes = [
-            "openid",
-            "profile",
-            "email",
-            "offline_access",  # Critical for background operations
-            "notes:read",
-            "notes:write",
-            "calendar:read",
-            "calendar:write",
-            "contacts:read",
-            "contacts:write",
-            "files:read",
-            "files:write",
-        ]
-
-        # Generate authorization URL
-        auth_url = generate_oauth_url_for_flow2(
-            oidc_discovery_url=oidc_discovery_url,
-            server_client_id=server_client_id,
-            redirect_uri=redirect_uri,
-            state=state,
-            scopes=scopes,
-        )
 
         return ProvisioningResult(
             success=True,
-            authorization_url=auth_url,
+            provisioning_url=astrolabe_url,
             message=(
-                "Please visit the authorization URL to grant the MCP server "
+                "Visit Astrolabe settings to provision background sync access.\n\n"
-                "offline access to your Nextcloud resources. This is a one-time "
+                "You can choose either:\n"
-                "setup that allows the server to access Nextcloud on your behalf "
+                "- App password (works today, recommended for now)\n"
-                "even when you're not actively connected."
+                "- OAuth refresh token (future, when Nextcloud fully supports OAuth)\n\n"
+                "After provisioning, background sync will enable the MCP server to "
+                "access Nextcloud resources even when you're not actively connected."
             ),
         )
 
@@ -417,11 +376,12 @@ async def revoke_nextcloud_access(
         storage = RefreshTokenStorage.from_env()
         await storage.initialize()
 
-        encryption_key = os.getenv("TOKEN_ENCRYPTION_KEY")
+        # Get OAuth client credentials from storage
-        if not encryption_key:
+        client_creds = await storage.get_oauth_client()
+        if not client_creds:
             return RevocationResult(
                 success=False,
-                message="Token encryption key not configured.",
+                message="OAuth client credentials not found in storage.",
             )
 
         broker = TokenBrokerService(
@@ -431,7 +391,8 @@ async def revoke_nextcloud_access(
                 f"{os.getenv('NEXTCLOUD_HOST')}/.well-known/openid-configuration",
             ),
             nextcloud_host=os.getenv("NEXTCLOUD_HOST"),  # type: ignore
-            encryption_key=encryption_key,
+            client_id=client_creds["client_id"],
+            client_secret=client_creds["client_secret"],
         )
 
         # Revoke access
@@ -684,11 +645,16 @@ def register_oauth_tools(mcp):
 
     @mcp.tool(
         name="provision_nextcloud_access",
+        title="Grant Server Access to Nextcloud",
         description=(
             "Provision offline access to Nextcloud resources. "
             "This is required before using Nextcloud tools. "
             "You'll need to complete an OAuth authorization in your browser."
         ),
+        annotations=ToolAnnotations(
+            idempotentHint=False,  # Creates new OAuth session each time
+            openWorldHint=True,
+        ),
     )
     @require_scopes("openid")
     async def tool_provision_access(
@@ -699,7 +665,13 @@ def register_oauth_tools(mcp):
 
     @mcp.tool(
         name="revoke_nextcloud_access",
+        title="Revoke Server Access to Nextcloud",
         description="Revoke offline access to Nextcloud resources.",
+        annotations=ToolAnnotations(
+            destructiveHint=True,  # Removes stored access tokens
+            idempotentHint=True,  # Revoking revoked access = same end state
+            openWorldHint=True,
+        ),
     )
     @require_scopes("openid")
     async def tool_revoke_access(
@@ -709,7 +681,12 @@ def register_oauth_tools(mcp):
 
     @mcp.tool(
         name="check_provisioning_status",
+        title="Check Provisioning Status",
         description="Check whether Nextcloud access is provisioned.",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Only checks status, doesn't modify
+            openWorldHint=True,
+        ),
     )
     @require_scopes("openid")
     async def tool_check_status(
@@ -719,10 +696,15 @@ def register_oauth_tools(mcp):
 
     @mcp.tool(
         name="check_logged_in",
+        title="Check Server Login Status",
         description=(
             "Check if you are logged in to Nextcloud. "
             "If not logged in, this tool will prompt you to complete the login flow."
         ),
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Checking status doesn't modify state
+            openWorldHint=True,
+        ),
     )
     @require_scopes("openid")
     async def tool_check_logged_in(ctx: Context, user_id: Optional[str] = None) -> str:

nextcloud_mcp_server/server/semantic.py

@@ -12,6 +12,7 @@ from mcp.types import (
     ModelPreferences,
     SamplingMessage,
     TextContent,
+    ToolAnnotations,
 )
 
 from nextcloud_mcp_server.auth import require_scopes
@@ -34,7 +35,13 @@ logger = logging.getLogger(__name__)
 def configure_semantic_tools(mcp: FastMCP):
     """Configure semantic search tools for MCP server."""
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Semantic Search",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Search doesn't modify data
+            openWorldHint=True,  # Queries external Nextcloud service
+        ),
+    )
     @require_scopes("semantic:read")
     @instrument_tool
     async def nc_semantic_search(
@@ -58,13 +65,13 @@ def configure_semantic_tools(mcp: FastMCP):
         database for optimal relevance. This provides the best of both semantic
         understanding and keyword precision.
 
-        Requires VECTOR_SYNC_ENABLED=true. Currently only "note" documents are
+        Requires VECTOR_SYNC_ENABLED=true. Supports indexing of notes, files,
-        fully supported for indexing.
+        news items, and deck cards.
 
         Args:
             query: Natural language or keyword search query
             limit: Maximum number of results to return (default: 10)
-            doc_types: Document types to search (e.g., ["note", "file"]). None = search all indexed types (default)
+            doc_types: Document types to search (e.g., ["note", "file", "deck_card", "news_item"]). None = search all indexed types (default)
             score_threshold: Minimum fusion score (0-1, default: 0.0)
             fusion: Fusion algorithm: "rrf" (Reciprocal Rank Fusion, default) or "dbsf" (Distribution-Based Score Fusion)
                    RRF: Good general-purpose fusion using reciprocal ranks
@@ -285,7 +292,13 @@ def configure_semantic_tools(mcp: FastMCP):
             logger.error(f"Search error: {e}", exc_info=True)
             raise McpError(ErrorData(code=-1, message=f"Search failed: {str(e)}"))
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Search with AI-Generated Answer",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Search doesn't modify data
+            openWorldHint=False,  # Searches only indexed Nextcloud data
+        ),
+    )
     @require_scopes("semantic:read")
     @instrument_tool
     async def nc_semantic_search_answer(
@@ -499,9 +512,11 @@ def configure_semantic_tools(mcp: FastMCP):
         )
 
         # 6. Request LLM completion via MCP sampling with timeout
+        # Note: 5 minute timeout to accommodate slower local LLMs (e.g., Ollama)
+        sampling_timeout_seconds = 300
 
         try:
-            with anyio.fail_after(30):
+            with anyio.fail_after(sampling_timeout_seconds):
                 sampling_result = await ctx.session.create_message(
                     messages=[
                         SamplingMessage(
@@ -548,14 +563,14 @@ def configure_semantic_tools(mcp: FastMCP):
 
         except TimeoutError:
             logger.warning(
-                f"Sampling request timed out after 30 seconds for query: '{query}', "
+                f"Sampling request timed out after {sampling_timeout_seconds} seconds for query: '{query}', "
                 f"returning search results only"
             )
             return SamplingSearchResponse(
                 query=query,
                 generated_answer=(
                     f"[Sampling request timed out]\n\n"
-                    f"The answer generation took too long (>30s). "
+                    f"The answer generation took too long (>{sampling_timeout_seconds}s). "
                     f"Found {len(accessible_results)} relevant documents. "
                     f"Please review the sources below or try a simpler query."
                 ),
@@ -621,7 +636,13 @@ def configure_semantic_tools(mcp: FastMCP):
                 success=True,
             )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Check Indexing Status",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,  # Only checks status
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("semantic:read")
     @instrument_tool
     async def nc_get_vector_sync_status(ctx: Context) -> VectorSyncStatusResponse:
@@ -675,15 +696,22 @@ def configure_semantic_tools(mcp: FastMCP):
             # Get Qdrant client and query indexed count
             indexed_count = 0
             try:
+                from qdrant_client.models import Filter
+
                 from nextcloud_mcp_server.config import get_settings
+                from nextcloud_mcp_server.vector.placeholder import (
+                    get_placeholder_filter,
+                )
                 from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
 
                 settings = get_settings()
                 qdrant_client = await get_qdrant_client()
 
-                # Count documents in collection
+                # Count documents in collection, excluding placeholders
+                # Placeholders are zero-vector points used to track processing state
                 count_result = await qdrant_client.count(
-                    collection_name=settings.get_collection_name()
+                    collection_name=settings.get_collection_name(),
+                    count_filter=Filter(must=[get_placeholder_filter()]),
                 )
                 indexed_count = count_result.count
 

nextcloud_mcp_server/server/sharing.py

@@ -3,6 +3,7 @@
 import json
 
 from mcp.server.fastmcp import Context, FastMCP
+from mcp.types import ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -16,7 +17,10 @@ def configure_sharing_tools(mcp: FastMCP):
         mcp: FastMCP server instance
     """
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Share",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("sharing:write")
     @instrument_tool
     async def nc_share_create(
@@ -56,7 +60,12 @@ def configure_sharing_tools(mcp: FastMCP):
         )
         return json.dumps(share_data, indent=2)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Share",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("sharing:write")
     @instrument_tool
     async def nc_share_delete(share_id: int, ctx: Context) -> str:
@@ -76,7 +85,10 @@ def configure_sharing_tools(mcp: FastMCP):
             {"success": True, "message": f"Share {share_id} deleted"}, indent=2
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Share Details",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("sharing:write")
     @instrument_tool
     async def nc_share_get(share_id: int, ctx: Context) -> str:
@@ -95,7 +107,10 @@ def configure_sharing_tools(mcp: FastMCP):
         share_data = await client.sharing.get_share(share_id)
         return json.dumps(share_data, indent=2)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Shares",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("sharing:write")
     @instrument_tool
     async def nc_share_list(
@@ -117,7 +132,10 @@ def configure_sharing_tools(mcp: FastMCP):
         )
         return json.dumps(shares, indent=2)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Share",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("sharing:write")
     @instrument_tool
     async def nc_share_update(share_id: int, permissions: int, ctx: Context) -> str:

nextcloud_mcp_server/server/tables.py

@@ -1,6 +1,7 @@
 import logging
 
 from mcp.server.fastmcp import Context, FastMCP
+from mcp.types import ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -11,7 +12,10 @@ logger = logging.getLogger(__name__)
 
 def configure_tables_tools(mcp: FastMCP):
     # Tables tools
-    @mcp.tool()
+    @mcp.tool(
+        title="List Tables",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("tables:read")
     @instrument_tool
     async def nc_tables_list_tables(ctx: Context):
@@ -19,7 +23,10 @@ def configure_tables_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.tables.list_tables()
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Get Table Schema",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("tables:read")
     @instrument_tool
     async def nc_tables_get_schema(table_id: int, ctx: Context):
@@ -27,7 +34,10 @@ def configure_tables_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.tables.get_table_schema(table_id)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Read Table Rows",
+        annotations=ToolAnnotations(readOnlyHint=True, openWorldHint=True),
+    )
     @require_scopes("tables:read")
     @instrument_tool
     async def nc_tables_read_table(
@@ -40,7 +50,10 @@ def configure_tables_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.tables.get_table_rows(table_id, limit, offset)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Insert Table Row",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("tables:write")
     @instrument_tool
     async def nc_tables_insert_row(table_id: int, data: dict, ctx: Context):
@@ -51,7 +64,10 @@ def configure_tables_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.tables.create_row(table_id, data)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Update Table Row",
+        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+    )
     @require_scopes("tables:write")
     @instrument_tool
     async def nc_tables_update_row(row_id: int, data: dict, ctx: Context):
@@ -62,7 +78,12 @@ def configure_tables_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.tables.update_row(row_id, data)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete Table Row",
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
+    )
     @require_scopes("tables:write")
     @instrument_tool
     async def nc_tables_delete_row(row_id: int, ctx: Context):

nextcloud_mcp_server/server/webdav.py

@@ -1,6 +1,7 @@
 import logging
 
 from mcp.server.fastmcp import Context, FastMCP
+from mcp.types import ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
@@ -16,7 +17,13 @@ logger = logging.getLogger(__name__)
 
 def configure_webdav_tools(mcp: FastMCP):
     # WebDAV file system tools
-    @mcp.tool()
+    @mcp.tool(
+        title="List Files and Directories",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:read")
     @instrument_tool
     async def nc_webdav_list_directory(
@@ -50,7 +57,13 @@ def configure_webdav_tools(mcp: FastMCP):
             total_size=total_size,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Read File",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:read")
     @instrument_tool
     async def nc_webdav_read_file(path: str, ctx: Context):
@@ -117,7 +130,13 @@ def configure_webdav_tools(mcp: FastMCP):
             "encoding": "base64",
         }
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Write File",
+        annotations=ToolAnnotations(
+            idempotentHint=True,  # HTTP PUT without version control is idempotent
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:write")
     @instrument_tool
     async def nc_webdav_write_file(
@@ -146,7 +165,13 @@ def configure_webdav_tools(mcp: FastMCP):
 
         return await client.webdav.write_file(path, content_bytes, content_type)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Create Directory",
+        annotations=ToolAnnotations(
+            idempotentHint=True,  # Creating existing dir returns 405 = same end state
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:write")
     @instrument_tool
     async def nc_webdav_create_directory(path: str, ctx: Context):
@@ -161,7 +186,14 @@ def configure_webdav_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.webdav.create_directory(path)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Delete File or Directory",
+        annotations=ToolAnnotations(
+            destructiveHint=True,  # Permanently deletes data
+            idempotentHint=True,  # Deleting deleted resource = same end state
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:write")
     @instrument_tool
     async def nc_webdav_delete_resource(path: str, ctx: Context):
@@ -176,7 +208,13 @@ def configure_webdav_tools(mcp: FastMCP):
         client = await get_client(ctx)
         return await client.webdav.delete_resource(path)
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Move or Rename File",
+        annotations=ToolAnnotations(
+            idempotentHint=False,  # Moving changes source and dest
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:write")
     @instrument_tool
     async def nc_webdav_move_resource(
@@ -197,7 +235,13 @@ def configure_webdav_tools(mcp: FastMCP):
             source_path, destination_path, overwrite
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Copy File or Directory",
+        annotations=ToolAnnotations(
+            idempotentHint=False,  # Creates new resource each time
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:write")
     @instrument_tool
     async def nc_webdav_copy_resource(
@@ -218,7 +262,13 @@ def configure_webdav_tools(mcp: FastMCP):
             source_path, destination_path, overwrite
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Search Files",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:read")
     @instrument_tool
     async def nc_webdav_search_files(
@@ -335,7 +385,13 @@ def configure_webdav_tools(mcp: FastMCP):
             filters_applied=filters if filters else None,
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Find Files by Name",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:read")
     @instrument_tool
     async def nc_webdav_find_by_name(
@@ -363,7 +419,13 @@ def configure_webdav_tools(mcp: FastMCP):
             filters_applied={"name_pattern": pattern},
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="Find Files by Type",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:read")
     @instrument_tool
     async def nc_webdav_find_by_type(
@@ -391,7 +453,13 @@ def configure_webdav_tools(mcp: FastMCP):
             filters_applied={"mime_type": mime_type},
         )
 
-    @mcp.tool()
+    @mcp.tool(
+        title="List Favorite Files",
+        annotations=ToolAnnotations(
+            readOnlyHint=True,
+            openWorldHint=True,
+        ),
+    )
     @require_scopes("files:read")
     @instrument_tool
     async def nc_webdav_list_favorites(

nextcloud_mcp_server/vector/html_processor.py

@@ -0,0 +1,49 @@
+"""HTML to Markdown conversion utilities for vector sync."""
+
+import logging
+
+from markdownify import markdownify as md
+
+logger = logging.getLogger(__name__)
+
+
+def html_to_markdown(html_content: str | None) -> str:
+    """Convert HTML content to Markdown, preserving semantic structure.
+
+    This function converts HTML (typically from RSS/Atom feed items) to Markdown
+    for better text embedding. Markdown preserves:
+    - Heading hierarchy (important for document structure)
+    - Lists (bullet and numbered)
+    - Links (as [text](url))
+    - Bold/italic emphasis
+    - Paragraphs and line breaks
+
+    Args:
+        html_content: HTML string to convert (may be None or empty)
+
+    Returns:
+        Markdown string, or empty string if input is None/empty
+
+    Example:
+        >>> html_to_markdown("<h1>Title</h1><p>Content with <b>bold</b>.</p>")
+        '# Title\\n\\nContent with **bold**.\\n\\n'
+    """
+    if not html_content:
+        return ""
+
+    try:
+        markdown = md(
+            html_content,
+            heading_style="ATX",  # Use # style headings
+            strip=["script", "style", "iframe", "noscript"],  # Remove unsafe elements
+            bullets="-",  # Use - for unordered lists
+            code_language="",  # Don't add language hints to code blocks
+        )
+        return markdown.strip()
+    except Exception as e:
+        logger.warning(f"Failed to convert HTML to Markdown: {e}")
+        # Fallback: strip all HTML tags as a last resort
+        import re
+
+        text = re.sub(r"<[^>]+>", " ", html_content)
+        return " ".join(text.split())  # Normalize whitespace

nextcloud_mcp_server/vector/oauth_sync.py

@@ -0,0 +1,392 @@
+"""OAuth mode vector sync orchestration.
+
+Manages multi-user background vector sync when running in OAuth mode
+with ENABLE_OFFLINE_ACCESS=true:
+- User Manager: Monitors RefreshTokenStorage for user changes
+- Per-User Scanners: One scanner task per provisioned user
+- Shared Processor Pool: Processes documents from all users
+
+Supports dual credential types for background sync:
+- App passwords (interim solution, works today)
+- OAuth refresh tokens (future, when Nextcloud supports OAuth for app APIs)
+"""
+
+import logging
+import time
+from dataclasses import dataclass, field
+from typing import TYPE_CHECKING
+
+import anyio
+from anyio.abc import TaskGroup, TaskStatus
+from anyio.streams.memory import (
+    MemoryObjectReceiveStream,
+    MemoryObjectSendStream,
+)
+from httpx import BasicAuth
+
+from nextcloud_mcp_server.auth.astrolabe_client import AstrolabeClient
+from nextcloud_mcp_server.client import NextcloudClient
+from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.vector.scanner import DocumentTask, scan_user_documents
+
+if TYPE_CHECKING:
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+    from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
+
+logger = logging.getLogger(__name__)
+
+# Scopes required for vector sync operations
+VECTOR_SYNC_SCOPES = [
+    "notes:read",
+    "files:read",
+    "deck:read",
+    # "news:read",  # News app may not be installed
+]
+
+
+class NotProvisionedError(Exception):
+    """User has not provisioned offline access or has revoked it."""
+
+    pass
+
+
+@dataclass
+class UserSyncState:
+    """State for a single user's scanner task."""
+
+    user_id: str
+    cancel_scope: anyio.CancelScope
+    started_at: float = field(default_factory=time.time)
+
+
+async def get_user_client(
+    user_id: str,
+    token_broker: "TokenBrokerService",
+    nextcloud_host: str,
+) -> NextcloudClient:
+    """Get an authenticated NextcloudClient for a user.
+
+    Supports dual credential types with priority:
+    1. App password from Astrolabe (works today with BasicAuth)
+    2. OAuth refresh token from storage (for future when OAuth fully supported)
+
+    Args:
+        user_id: User identifier
+        token_broker: Token broker for obtaining access tokens
+        nextcloud_host: Nextcloud base URL
+
+    Returns:
+        Authenticated NextcloudClient
+
+    Raises:
+        NotProvisionedError: If user has not provisioned offline access
+    """
+    settings = get_settings()
+
+    # Try app password first (interim solution, works today)
+    if settings.oidc_client_id and settings.oidc_client_secret:
+        try:
+            astrolabe = AstrolabeClient(
+                nextcloud_host=nextcloud_host,
+                client_id=settings.oidc_client_id,
+                client_secret=settings.oidc_client_secret,
+            )
+            app_password = await astrolabe.get_user_app_password(user_id)
+
+            if app_password:
+                logger.info(
+                    f"Using app password for background sync: {user_id} "
+                    f"(credential_type=app_password)"
+                )
+                return NextcloudClient(
+                    base_url=nextcloud_host,
+                    username=user_id,
+                    auth=BasicAuth(user_id, app_password),
+                )
+        except Exception as e:
+            logger.debug(f"App password not available for {user_id}: {e}")
+
+    # Fall back to OAuth refresh token
+    logger.info(
+        f"Using OAuth refresh token for background sync: {user_id} "
+        f"(credential_type=refresh_token)"
+    )
+    token = await token_broker.get_background_token(user_id, VECTOR_SYNC_SCOPES)
+    if not token:
+        raise NotProvisionedError(f"User {user_id} has not provisioned offline access")
+
+    return NextcloudClient.from_token(
+        base_url=nextcloud_host,
+        token=token,
+        username=user_id,
+    )
+
+
+async def user_scanner_task(
+    user_id: str,
+    send_stream: MemoryObjectSendStream[DocumentTask],
+    shutdown_event: anyio.Event,
+    wake_event: anyio.Event,
+    token_broker: "TokenBrokerService",
+    nextcloud_host: str,
+    *,
+    task_status: TaskStatus = anyio.TASK_STATUS_IGNORED,
+) -> None:
+    """Scanner task for a single user in OAuth mode.
+
+    Gets a fresh token at the start of each scan cycle.
+
+    Args:
+        user_id: User to scan
+        send_stream: Stream to send changed documents to processors
+        shutdown_event: Event signaling shutdown
+        wake_event: Event to trigger immediate scan
+        token_broker: Token broker for obtaining access tokens
+        nextcloud_host: Nextcloud base URL
+        task_status: Status object for signaling task readiness
+    """
+    logger.info(f"[OAuth] Scanner started for user: {user_id}")
+    settings = get_settings()
+
+    task_status.started()
+
+    while not shutdown_event.is_set():
+        nc_client = None
+        try:
+            # Get fresh token for this scan cycle
+            nc_client = await get_user_client(user_id, token_broker, nextcloud_host)
+
+            # Scan user's documents
+            await scan_user_documents(
+                user_id=user_id,
+                send_stream=send_stream,
+                nc_client=nc_client,
+            )
+
+        except NotProvisionedError:
+            logger.warning(
+                f"[OAuth] User {user_id} no longer provisioned, stopping scanner"
+            )
+            break
+
+        except Exception as e:
+            logger.error(f"[OAuth] Scanner error for {user_id}: {e}", exc_info=True)
+
+        finally:
+            if nc_client:
+                await nc_client.close()
+
+        # Sleep until next interval or wake event
+        try:
+            with anyio.move_on_after(settings.vector_sync_scan_interval):
+                await wake_event.wait()
+        except anyio.get_cancelled_exc_class():
+            break
+
+    logger.info(f"[OAuth] Scanner stopped for user: {user_id}")
+
+
+async def oauth_processor_task(
+    worker_id: int,
+    receive_stream: MemoryObjectReceiveStream[DocumentTask],
+    shutdown_event: anyio.Event,
+    token_broker: "TokenBrokerService",
+    nextcloud_host: str,
+    *,
+    task_status: TaskStatus = anyio.TASK_STATUS_IGNORED,
+) -> None:
+    """Processor task for OAuth mode.
+
+    Handles documents from any user by fetching tokens on-demand.
+
+    Args:
+        worker_id: Worker identifier for logging
+        receive_stream: Stream to receive documents from
+        shutdown_event: Event signaling shutdown
+        token_broker: Token broker for obtaining access tokens
+        nextcloud_host: Nextcloud base URL
+        task_status: Status object for signaling task readiness
+    """
+    from nextcloud_mcp_server.vector.processor import process_document
+
+    logger.info(f"[OAuth] Processor {worker_id} started")
+    task_status.started()
+
+    while not shutdown_event.is_set():
+        doc_task = None
+        nc_client = None
+        try:
+            # Get document with timeout
+            with anyio.fail_after(1.0):
+                doc_task = await receive_stream.receive()
+
+            # Get token for THIS document's user
+            nc_client = await get_user_client(
+                doc_task.user_id, token_broker, nextcloud_host
+            )
+
+            # Process the document
+            await process_document(doc_task, nc_client)
+
+        except TimeoutError:
+            continue
+
+        except anyio.EndOfStream:
+            logger.info(f"[OAuth] Processor {worker_id}: Stream closed, exiting")
+            break
+
+        except NotProvisionedError:
+            if doc_task:
+                logger.warning(
+                    f"[OAuth] User {doc_task.user_id} not provisioned, "
+                    f"skipping {doc_task.doc_type}_{doc_task.doc_id}"
+                )
+            continue
+
+        except Exception as e:
+            if doc_task:
+                logger.error(
+                    f"[OAuth] Processor {worker_id} error processing "
+                    f"{doc_task.doc_type}_{doc_task.doc_id}: {e}",
+                    exc_info=True,
+                )
+            else:
+                logger.error(f"[OAuth] Processor {worker_id} error: {e}", exc_info=True)
+
+        finally:
+            if nc_client:
+                await nc_client.close()
+
+    logger.info(f"[OAuth] Processor {worker_id} stopped")
+
+
+async def _run_user_scanner_with_scope(
+    user_id: str,
+    cancel_scope: anyio.CancelScope,
+    send_stream: MemoryObjectSendStream[DocumentTask],
+    shutdown_event: anyio.Event,
+    wake_event: anyio.Event,
+    token_broker: "TokenBrokerService",
+    nextcloud_host: str,
+    user_states: dict[str, UserSyncState],
+) -> None:
+    """Wrapper to run scanner with cancellation scope.
+
+    Cleans up user state on exit.
+    """
+    cloned_stream = send_stream.clone()
+    try:
+        with cancel_scope:
+            await user_scanner_task(
+                user_id=user_id,
+                send_stream=cloned_stream,
+                shutdown_event=shutdown_event,
+                wake_event=wake_event,
+                token_broker=token_broker,
+                nextcloud_host=nextcloud_host,
+            )
+    finally:
+        # Clean up on exit
+        if user_id in user_states:
+            del user_states[user_id]
+        await cloned_stream.aclose()
+
+
+async def user_manager_task(
+    send_stream: MemoryObjectSendStream[DocumentTask],
+    shutdown_event: anyio.Event,
+    wake_event: anyio.Event,
+    token_broker: "TokenBrokerService",
+    refresh_token_storage: "RefreshTokenStorage",
+    nextcloud_host: str,
+    user_states: dict[str, UserSyncState],
+    tg: TaskGroup,
+    *,
+    task_status: TaskStatus = anyio.TASK_STATUS_IGNORED,
+) -> None:
+    """Supervisor task that manages per-user scanners.
+
+    Periodically polls RefreshTokenStorage to detect:
+    - New users who have provisioned offline access -> start scanner
+    - Users who have revoked access -> cancel their scanner
+
+    Args:
+        send_stream: Stream to send documents to processors
+        shutdown_event: Event signaling shutdown
+        wake_event: Event to wake scanners for immediate scan
+        token_broker: Token broker for obtaining access tokens
+        refresh_token_storage: Storage for refresh tokens
+        nextcloud_host: Nextcloud base URL
+        user_states: Shared dict tracking active user scanners
+        tg: Task group for spawning scanner tasks
+        task_status: Status object for signaling task readiness
+    """
+    settings = get_settings()
+    poll_interval = settings.vector_sync_user_poll_interval
+
+    logger.info(f"[OAuth] User manager started (poll interval: {poll_interval}s)")
+    task_status.started()
+
+    while not shutdown_event.is_set():
+        try:
+            # Get current provisioned users
+            provisioned_users = set(await refresh_token_storage.get_all_user_ids())
+            active_users = set(user_states.keys())
+
+            # Start scanners for new users
+            new_users = provisioned_users - active_users
+            for user_id in new_users:
+                logger.info(
+                    f"[OAuth] Starting scanner for newly provisioned user: {user_id}"
+                )
+                cancel_scope = anyio.CancelScope()
+                user_states[user_id] = UserSyncState(
+                    user_id=user_id,
+                    cancel_scope=cancel_scope,
+                )
+
+                # Start scanner in task group
+                tg.start_soon(
+                    _run_user_scanner_with_scope,
+                    user_id,
+                    cancel_scope,
+                    send_stream,
+                    shutdown_event,
+                    wake_event,
+                    token_broker,
+                    nextcloud_host,
+                    user_states,
+                )
+
+            # Cancel scanners for revoked users
+            revoked_users = active_users - provisioned_users
+            for user_id in revoked_users:
+                logger.info(f"[OAuth] Stopping scanner for revoked user: {user_id}")
+                state = user_states.get(user_id)
+                if state:
+                    state.cancel_scope.cancel()
+                    # Note: state will be removed by _run_user_scanner_with_scope on exit
+
+            if new_users:
+                logger.info(f"[OAuth] Started {len(new_users)} new scanner(s)")
+            if revoked_users:
+                logger.info(f"[OAuth] Stopped {len(revoked_users)} scanner(s)")
+
+        except Exception as e:
+            logger.error(f"[OAuth] User manager error: {e}", exc_info=True)
+
+        # Sleep until next poll
+        try:
+            with anyio.move_on_after(poll_interval):
+                await shutdown_event.wait()
+        except anyio.get_cancelled_exc_class():
+            break
+
+    # Cancel all remaining scanners on shutdown
+    logger.info(
+        f"[OAuth] User manager shutting down, cancelling {len(user_states)} scanner(s)"
+    )
+    for state in list(user_states.values()):
+        state.cancel_scope.cancel()
+
+    logger.info("[OAuth] User manager stopped")

nextcloud_mcp_server/vector/processor.py

@@ -6,6 +6,7 @@ Processes documents from stream: fetches content, generates embeddings, stores i
 import logging
 import time
 import uuid
+from typing import Any, cast
 
 import anyio
 from anyio.abc import TaskStatus
@@ -272,6 +273,141 @@ async def _index_document(
             file_path = None  # Notes don't have file paths
             content_bytes = None  # Notes don't have binary content
             content_type = None
+        elif doc_task.doc_type == "news_item":
+            from nextcloud_mcp_server.vector.html_processor import html_to_markdown
+
+            item = await nc_client.news.get_item(int(doc_task.doc_id))
+            # Convert HTML body to Markdown for better embedding
+            body_markdown = html_to_markdown(item.get("body", ""))
+            # Build content: title + URL + body
+            item_title = item.get("title", "")
+            item_url = item.get("url", "")
+            feed_title = item.get("feedTitle", "")
+
+            # Structure content for embedding
+            content_parts = [item_title]
+            if feed_title:
+                content_parts.append(f"Source: {feed_title}")
+            if item_url:
+                content_parts.append(f"URL: {item_url}")
+            content_parts.append("")  # Blank line
+            content_parts.append(body_markdown)
+            content = "\n".join(content_parts)
+
+            title = item_title
+            etag = item.get("guidHash", "")
+            # Store news-specific metadata for later use in payload
+            file_metadata = {
+                "feed_id": item.get("feedId"),
+                "feed_title": feed_title,
+                "author": item.get("author"),
+                "pub_date": item.get("pubDate"),
+                "starred": item.get("starred", False),
+                "unread": item.get("unread", True),
+                "url": item_url,
+                "guid_hash": item.get("guidHash"),
+                "enclosure_link": item.get("enclosureLink"),
+                "enclosure_mime": item.get("enclosureMime"),
+            }
+            file_path = None
+            content_bytes = None
+            content_type = None
+        elif doc_task.doc_type == "deck_card":
+            # Fetch card from Deck API
+            # Use metadata from scanner if available (O(1) lookup)
+            # Otherwise fall back to iteration (legacy data)
+            card = None
+            board = None
+            stack = None
+
+            if (
+                doc_task.metadata
+                and "board_id" in doc_task.metadata
+                and "stack_id" in doc_task.metadata
+            ):
+                # Fast path: Direct lookup with known board_id/stack_id
+                board_id = doc_task.metadata["board_id"]
+                stack_id = doc_task.metadata["stack_id"]
+                try:
+                    card = await nc_client.deck.get_card(
+                        board_id=int(board_id),
+                        stack_id=int(stack_id),
+                        card_id=int(doc_task.doc_id),
+                    )
+                    # Fetch board and stack info for metadata
+                    boards = await nc_client.deck.get_boards()
+                    for b in boards:
+                        if b.id == int(board_id):
+                            board = b
+                            stacks = await nc_client.deck.get_stacks(b.id)
+                            for s in stacks:
+                                if s.id == int(stack_id):
+                                    stack = s
+                                    break
+                            break
+                except Exception as e:
+                    logger.warning(
+                        f"Failed to fetch card with metadata (board_id={board_id}, stack_id={stack_id}, card_id={doc_task.doc_id}): {e}, falling back to iteration"
+                    )
+
+            # Fallback: Iterate through all boards/stacks (for legacy data or if fast path failed)
+            if card is None:
+                boards = await nc_client.deck.get_boards()
+                card_found = False
+
+                for b in boards:
+                    if card_found:
+                        break
+                    # Skip deleted boards (soft delete: deletedAt > 0)
+                    if b.deletedAt > 0:
+                        continue
+                    stacks = await nc_client.deck.get_stacks(b.id)
+                    for s in stacks:
+                        if card_found:
+                            break
+                        if s.cards:
+                            for c in s.cards:
+                                if c.id == int(doc_task.doc_id):
+                                    card = c
+                                    board = b
+                                    stack = s
+                                    card_found = True
+                                    break
+
+                if not card_found:
+                    raise ValueError(
+                        f"Deck card {doc_task.doc_id} not found in any board/stack"
+                    )
+
+            # Type narrowing: card, board, stack are all set if we reach here
+            assert card is not None
+            assert board is not None
+            assert stack is not None
+
+            # Build content from card title and description
+            content_parts = [card.title]
+            if card.description:
+                content_parts.append(card.description)
+            content = "\n\n".join(content_parts)
+            title = card.title
+
+            # Store deck-specific metadata
+            file_metadata = {
+                "board_id": board.id,
+                "board_title": board.title,
+                "stack_id": stack.id,
+                "stack_title": stack.title,
+                "card_type": card.type,
+                "duedate": (card.duedate.isoformat() if card.duedate else None),
+                "archived": card.archived,
+                "owner": (
+                    card.owner.uid if hasattr(card.owner, "uid") else str(card.owner)
+                ),
+            }
+            etag = card.etag or ""
+            file_path = None
+            content_bytes = None
+            content_type = None
         elif doc_task.doc_type == "file":
             # For files, doc_id is now the numeric file ID, file_path comes from DocumentTask
             if not doc_task.file_path:
@@ -358,15 +494,18 @@ async def _index_document(
         chunks = await chunker.chunk_text(content)
 
     # Assign page numbers to chunks if page boundaries are available (PDFs)
-    if doc_task.doc_type == "file" and "page_boundaries" in file_metadata:
+    page_boundaries = file_metadata.get("page_boundaries")
+    if doc_task.doc_type == "file" and page_boundaries is not None:
+        # Type narrowing: page_boundaries is guaranteed to be list[dict] here
+        page_boundaries_list = cast(list[dict[str, Any]], page_boundaries)
         with trace_operation(
             "vector_sync.assign_page_numbers",
             attributes={
                 "vector_sync.chunk_count": len(chunks),
-                "vector_sync.page_count": len(file_metadata["page_boundaries"]),
+                "vector_sync.page_count": len(page_boundaries_list),
             },
         ):
-            assign_page_numbers(chunks, file_metadata["page_boundaries"])
+            assign_page_numbers(chunks, page_boundaries_list)
 
             # Diagnostic: Verify page number assignment
             assigned_count = sum(1 for c in chunks if c.page_number is not None)
@@ -389,8 +528,8 @@ async def _index_document(
                     f"Text length: {len(content)}, "
                     f"Chunks: {len(chunks)}, "
                     f"Chunk offset range: [{chunks[0].start_offset}:{chunks[-1].end_offset}], "
-                    f"Page boundaries: {len(file_metadata['page_boundaries'])} pages, "
+                    f"Page boundaries: {len(page_boundaries_list)} pages, "
-                    f"First boundary: {file_metadata['page_boundaries'][0] if file_metadata['page_boundaries'] else 'None'}"
+                    f"First boundary: {page_boundaries_list[0] if page_boundaries_list else 'None'}"
                 )
 
     # Extract chunk texts for embedding
@@ -464,6 +603,9 @@ async def _index_document(
                 logger.warning("No page boundaries available, skipping highlighting")
                 return
 
+            # Type narrowing: page_boundaries is guaranteed to be list[dict] here
+            page_boundaries_list = cast(list[dict[str, Any]], page_boundaries)
+
             logger.info(
                 f"Batch generating highlighted page images for {len(chunk_data)} PDF chunks"
             )
@@ -474,7 +616,7 @@ async def _index_document(
                 lambda: PDFHighlighter.highlight_chunks_batch(
                     pdf_bytes=content_bytes,
                     chunks=chunk_data,
-                    page_boundaries=page_boundaries,
+                    page_boundaries=page_boundaries_list,
                     full_text=content,
                     color="yellow",
                     zoom=2.0,
@@ -566,6 +708,37 @@ async def _index_document(
                         if doc_task.doc_type == "file"
                         else {}
                     ),
+                    # News item-specific metadata
+                    **(
+                        {
+                            "feed_id": file_metadata.get("feed_id"),
+                            "feed_title": file_metadata.get("feed_title"),
+                            "author": file_metadata.get("author"),
+                            "pub_date": file_metadata.get("pub_date"),
+                            "starred": file_metadata.get("starred"),
+                            "unread": file_metadata.get("unread"),
+                            "url": file_metadata.get("url"),
+                            "guid_hash": file_metadata.get("guid_hash"),
+                            "enclosure_link": file_metadata.get("enclosure_link"),
+                            "enclosure_mime": file_metadata.get("enclosure_mime"),
+                        }
+                        if doc_task.doc_type == "news_item"
+                        else {}
+                    ),
+                    # Deck card-specific metadata
+                    **(
+                        {
+                            "board_id": file_metadata.get("board_id"),
+                            "board_title": file_metadata.get("board_title"),
+                            "stack_id": file_metadata.get("stack_id"),
+                            "stack_title": file_metadata.get("stack_title"),
+                            "card_type": file_metadata.get("card_type"),
+                            "duedate": file_metadata.get("duedate"),
+                            "owner": file_metadata.get("owner"),
+                        }
+                        if doc_task.doc_type == "deck_card"
+                        else {}
+                    ),
                     # Highlighted page image (PDF only)
                     **(
                         {

nextcloud_mcp_server/vector/qdrant_client.py

@@ -89,6 +89,8 @@ async def get_qdrant_client() -> AsyncQdrantClient:
             if isinstance(vectors, dict):
                 actual_dimension = vectors["dense"].size
             else:
+                # Type narrowing: vectors must be VectorParams if not dict
+                assert isinstance(vectors, VectorParams)
                 actual_dimension = vectors.size
 
             # Validate dimension matches

nextcloud_mcp_server/vector/scanner.py

@@ -36,6 +36,9 @@ class DocumentTask:
     operation: str  # "index" or "delete"
     modified_at: int
     file_path: str | None = None  # File path for files (when doc_id is file_id)
+    metadata: dict[str, int | str] | None = (
+        None  # Additional metadata (e.g., board_id/stack_id for deck_card)
+    )
 
 
 # Track documents potentially deleted (grace period before actual deletion)
@@ -79,9 +82,11 @@ async def get_last_indexed_timestamp(user_id: str) -> int | None:
 
         if scroll_result[0]:
             timestamps = [
-                point.payload.get("indexed_at", 0) for point in scroll_result[0]
+                point.payload.get("indexed_at", 0)
+                for point in scroll_result[0]
+                if point.payload is not None
             ]
-            max_timestamp = max(timestamps)
+            max_timestamp = max(timestamps) if timestamps else 0
             logger.info(
                 f"Max indexed_at: {max_timestamp}, timestamps sample: {timestamps[:3]}"
             )
@@ -206,7 +211,11 @@ async def scan_user_documents(
                 limit=10000,
             )
 
-            indexed_doc_ids = {point.payload["doc_id"] for point in scroll_result[0]}
+            indexed_doc_ids = {
+                point.payload["doc_id"]
+                for point in (scroll_result[0] or [])
+                if point.payload is not None
+            }
 
             logger.debug(f"Found {len(indexed_doc_ids)} indexed documents in Qdrant")
 
@@ -376,7 +385,9 @@ async def scan_user_documents(
             )
 
             indexed_file_ids = {
-                point.payload["doc_id"] for point in file_scroll_result[0]
+                point.payload["doc_id"]
+                for point in (file_scroll_result[0] or [])
+                if point.payload is not None
             }
 
             logger.debug(f"Found {len(indexed_file_ids)} indexed files in Qdrant")
@@ -544,9 +555,419 @@ async def scan_user_documents(
 
         queued += file_queued
 
+        # Scan News items (starred + unread)
+        news_queued = 0
+        try:
+            news_queued = await scan_news_items(
+                user_id=user_id,
+                send_stream=send_stream,
+                nc_client=nc_client,
+                initial_sync=initial_sync,
+                scan_id=scan_id,
+            )
+            queued += news_queued
+        except Exception as e:
+            logger.warning(f"Failed to scan news items for {user_id}: {e}")
+
+        # Scan Deck cards
+        deck_queued = 0
+        try:
+            deck_queued = await scan_deck_cards(
+                user_id=user_id,
+                send_stream=send_stream,
+                nc_client=nc_client,
+                initial_sync=initial_sync,
+                scan_id=scan_id,
+            )
+            queued += deck_queued
+        except Exception as e:
+            logger.warning(f"Failed to scan deck cards for {user_id}: {e}")
+
         if queued > 0:
             logger.info(
-                f"Sent {queued} documents ({file_queued} files) for incremental sync: {user_id}"
+                f"Sent {queued} documents ({file_queued} files, {news_queued} news items, {deck_queued} deck cards) for incremental sync: {user_id}"
             )
         else:
             logger.debug(f"No changes detected for {user_id}")
+
+
+async def scan_news_items(
+    user_id: str,
+    send_stream: MemoryObjectSendStream[DocumentTask],
+    nc_client: NextcloudClient,
+    initial_sync: bool,
+    scan_id: int,
+) -> int:
+    """
+    Scan user's News items and queue changed items for indexing.
+
+    Indexes all items from the user's feeds. The News app's auto-purge
+    feature (default: 200 items per feed) naturally limits the total
+    number of items, making explicit filtering unnecessary.
+
+    Args:
+        user_id: User to scan
+        send_stream: Stream to send changed documents to processors
+        nc_client: Authenticated Nextcloud client
+        initial_sync: If True, send all documents (first-time sync)
+        scan_id: Scan identifier for logging
+
+    Returns:
+        Number of items queued for processing
+    """
+    from nextcloud_mcp_server.client.news import NewsItemType
+
+    settings = get_settings()
+    queued = 0
+
+    # Get indexed news item IDs from Qdrant (for deletion tracking)
+    indexed_item_ids: set[str] = set()
+    if not initial_sync:
+        qdrant_client = await get_qdrant_client()
+        scroll_result = await qdrant_client.scroll(
+            collection_name=settings.get_collection_name(),
+            scroll_filter=Filter(
+                must=[
+                    FieldCondition(key="user_id", match=MatchValue(value=user_id)),
+                    FieldCondition(key="doc_type", match=MatchValue(value="news_item")),
+                ]
+            ),
+            with_payload=["doc_id"],
+            with_vectors=False,
+            limit=10000,
+        )
+        indexed_item_ids = {
+            point.payload["doc_id"]
+            for point in (scroll_result[0] or [])
+            if point.payload is not None
+        }
+        logger.debug(f"Found {len(indexed_item_ids)} indexed news items in Qdrant")
+
+    # Fetch all items (News app caps at ~200 per feed via auto-purge)
+    all_items = await nc_client.news.get_items(
+        batch_size=-1,
+        type_=NewsItemType.ALL,
+        get_read=True,
+    )
+    logger.debug(f"[SCAN-{scan_id}] Found {len(all_items)} news items")
+
+    item_count = len(all_items)
+    nextcloud_item_ids: set[str] = set()
+
+    for item in all_items:
+        doc_id = str(item["id"])
+        nextcloud_item_ids.add(doc_id)
+
+        # Use lastModified timestamp (microseconds in News API)
+        modified_at = item.get("lastModified", 0)
+        # Convert to seconds if needed (News API uses microseconds)
+        if modified_at > 10000000000:  # > year 2286 in seconds
+            modified_at = modified_at // 1000000
+
+        if initial_sync:
+            # Send everything on first sync - write placeholder first
+            await write_placeholder_point(
+                doc_id=doc_id,
+                doc_type="news_item",
+                user_id=user_id,
+                modified_at=modified_at,
+            )
+            await send_stream.send(
+                DocumentTask(
+                    user_id=user_id,
+                    doc_id=doc_id,
+                    doc_type="news_item",
+                    operation="index",
+                    modified_at=modified_at,
+                )
+            )
+            queued += 1
+        else:
+            # Incremental sync: check if item exists and compare modified_at
+            doc_key = (user_id, doc_id)
+            if doc_key in _potentially_deleted:
+                logger.debug(
+                    f"News item {doc_id} reappeared, removing from deletion grace period"
+                )
+                del _potentially_deleted[doc_key]
+
+            # Query Qdrant for existing entry
+            existing_metadata = await query_document_metadata(
+                doc_id=doc_id, doc_type="news_item", user_id=user_id
+            )
+
+            needs_indexing = False
+            if existing_metadata is None:
+                needs_indexing = True
+            elif existing_metadata.get("modified_at", 0) < modified_at:
+                needs_indexing = True
+            elif existing_metadata.get("is_placeholder", False):
+                queued_at = existing_metadata.get("queued_at", 0)
+                placeholder_age = time.time() - queued_at
+                stale_threshold = settings.vector_sync_scan_interval * 5
+                if placeholder_age > stale_threshold:
+                    logger.debug(
+                        f"Found stale placeholder for news item {doc_id} "
+                        f"(age={placeholder_age:.1f}s), requeuing"
+                    )
+                    needs_indexing = True
+
+            if needs_indexing:
+                await write_placeholder_point(
+                    doc_id=doc_id,
+                    doc_type="news_item",
+                    user_id=user_id,
+                    modified_at=modified_at,
+                )
+                await send_stream.send(
+                    DocumentTask(
+                        user_id=user_id,
+                        doc_id=doc_id,
+                        doc_type="news_item",
+                        operation="index",
+                        modified_at=modified_at,
+                    )
+                )
+                queued += 1
+
+    logger.info(
+        f"[SCAN-{scan_id}] Found {item_count} news items (starred+unread) for {user_id}"
+    )
+    record_vector_sync_scan(item_count)
+
+    # Check for deleted items (not initial sync)
+    # Items become "deleted" when they are no longer starred AND become read
+    if not initial_sync:
+        grace_period = settings.vector_sync_scan_interval * 1.5
+        current_time = time.time()
+
+        for doc_id in indexed_item_ids:
+            if doc_id not in nextcloud_item_ids:
+                doc_key = (user_id, doc_id)
+
+                if doc_key in _potentially_deleted:
+                    first_missing_time = _potentially_deleted[doc_key]
+                    time_missing = current_time - first_missing_time
+
+                    if time_missing >= grace_period:
+                        logger.info(
+                            f"News item {doc_id} missing for {time_missing:.1f}s "
+                            f"(>{grace_period:.1f}s grace period), sending deletion"
+                        )
+                        await send_stream.send(
+                            DocumentTask(
+                                user_id=user_id,
+                                doc_id=doc_id,
+                                doc_type="news_item",
+                                operation="delete",
+                                modified_at=0,
+                            )
+                        )
+                        queued += 1
+                        del _potentially_deleted[doc_key]
+                else:
+                    logger.debug(
+                        f"News item {doc_id} missing for first time, starting grace period"
+                    )
+                    _potentially_deleted[doc_key] = current_time
+
+    return queued
+
+
+async def scan_deck_cards(
+    user_id: str,
+    send_stream: MemoryObjectSendStream[DocumentTask],
+    nc_client: NextcloudClient,
+    initial_sync: bool,
+    scan_id: int,
+) -> int:
+    """
+    Scan user's Deck cards and queue changed cards for indexing.
+
+    Indexes cards from all non-archived boards and stacks.
+
+    Args:
+        user_id: User to scan
+        send_stream: Stream to send changed documents to processors
+        nc_client: Authenticated Nextcloud client
+        initial_sync: If True, send all documents (first-time sync)
+        scan_id: Scan identifier for logging
+
+    Returns:
+        Number of cards queued for processing
+    """
+    settings = get_settings()
+    queued = 0
+
+    # Get indexed deck card IDs from Qdrant (for deletion tracking)
+    indexed_card_ids: set[str] = set()
+    if not initial_sync:
+        qdrant_client = await get_qdrant_client()
+        scroll_result = await qdrant_client.scroll(
+            collection_name=settings.get_collection_name(),
+            scroll_filter=Filter(
+                must=[
+                    FieldCondition(key="user_id", match=MatchValue(value=user_id)),
+                    FieldCondition(key="doc_type", match=MatchValue(value="deck_card")),
+                ]
+            ),
+            with_payload=["doc_id"],
+            with_vectors=False,
+            limit=10000,
+        )
+        indexed_card_ids = {
+            point.payload["doc_id"]
+            for point in (scroll_result[0] or [])
+            if point.payload is not None
+        }
+        logger.debug(f"Found {len(indexed_card_ids)} indexed deck cards in Qdrant")
+
+    # Fetch all boards
+    boards = await nc_client.deck.get_boards()
+    logger.debug(f"[SCAN-{scan_id}] Found {len(boards)} deck boards")
+
+    card_count = 0
+    nextcloud_card_ids: set[str] = set()
+
+    # Iterate through boards
+    for board in boards:
+        # Skip archived boards
+        if board.archived:
+            continue
+
+        # Skip deleted boards (soft delete: deletedAt > 0)
+        if board.deletedAt > 0:
+            logger.debug(f"[SCAN-{scan_id}] Skipping deleted board {board.id}")
+            continue
+
+        # Get stacks for this board
+        stacks = await nc_client.deck.get_stacks(board.id)
+
+        # Iterate through stacks
+        for stack in stacks:
+            # Skip if stack has no cards
+            if not stack.cards:
+                continue
+
+            # Iterate through cards in stack
+            for card in stack.cards:
+                # Skip archived cards
+                if card.archived:
+                    continue
+
+                card_count += 1
+                doc_id = str(card.id)
+                nextcloud_card_ids.add(doc_id)
+
+                # Use lastModified timestamp if available
+                modified_at = card.lastModified or 0
+
+                if initial_sync:
+                    # Send everything on first sync - write placeholder first
+                    await write_placeholder_point(
+                        doc_id=doc_id,
+                        doc_type="deck_card",
+                        user_id=user_id,
+                        modified_at=modified_at,
+                    )
+                    await send_stream.send(
+                        DocumentTask(
+                            user_id=user_id,
+                            doc_id=doc_id,
+                            doc_type="deck_card",
+                            operation="index",
+                            modified_at=modified_at,
+                            metadata={"board_id": board.id, "stack_id": stack.id},
+                        )
+                    )
+                    queued += 1
+                else:
+                    # Incremental sync: check if card exists and compare modified_at
+                    doc_key = (user_id, doc_id)
+                    if doc_key in _potentially_deleted:
+                        logger.debug(
+                            f"Deck card {doc_id} reappeared, removing from deletion grace period"
+                        )
+                        del _potentially_deleted[doc_key]
+
+                    # Query Qdrant for existing entry
+                    existing_metadata = await query_document_metadata(
+                        doc_id=doc_id, doc_type="deck_card", user_id=user_id
+                    )
+
+                    needs_indexing = False
+                    if existing_metadata is None:
+                        needs_indexing = True
+                    elif existing_metadata.get("modified_at", 0) < modified_at:
+                        needs_indexing = True
+                    elif existing_metadata.get("is_placeholder", False):
+                        queued_at = existing_metadata.get("queued_at", 0)
+                        placeholder_age = time.time() - queued_at
+                        stale_threshold = settings.vector_sync_scan_interval * 5
+                        if placeholder_age > stale_threshold:
+                            logger.debug(
+                                f"Found stale placeholder for deck card {doc_id} "
+                                f"(age={placeholder_age:.1f}s), requeuing"
+                            )
+                            needs_indexing = True
+
+                    if needs_indexing:
+                        await write_placeholder_point(
+                            doc_id=doc_id,
+                            doc_type="deck_card",
+                            user_id=user_id,
+                            modified_at=modified_at,
+                        )
+                        await send_stream.send(
+                            DocumentTask(
+                                user_id=user_id,
+                                doc_id=doc_id,
+                                doc_type="deck_card",
+                                operation="index",
+                                modified_at=modified_at,
+                                metadata={"board_id": board.id, "stack_id": stack.id},
+                            )
+                        )
+                        queued += 1
+
+    logger.info(
+        f"[SCAN-{scan_id}] Found {card_count} deck cards (non-archived) for {user_id}"
+    )
+    record_vector_sync_scan(card_count)
+
+    # Check for deleted cards (not initial sync)
+    if not initial_sync:
+        grace_period = settings.vector_sync_scan_interval * 1.5
+        current_time = time.time()
+
+        for doc_id in indexed_card_ids:
+            if doc_id not in nextcloud_card_ids:
+                doc_key = (user_id, doc_id)
+
+                if doc_key in _potentially_deleted:
+                    first_missing_time = _potentially_deleted[doc_key]
+                    time_missing = current_time - first_missing_time
+
+                    if time_missing >= grace_period:
+                        logger.info(
+                            f"Deck card {doc_id} missing for {time_missing:.1f}s "
+                            f"(>{grace_period:.1f}s grace period), sending deletion"
+                        )
+                        await send_stream.send(
+                            DocumentTask(
+                                user_id=user_id,
+                                doc_id=doc_id,
+                                doc_type="deck_card",
+                                operation="delete",
+                                modified_at=0,
+                            )
+                        )
+                        queued += 1
+                        del _potentially_deleted[doc_key]
+                else:
+                    logger.debug(
+                        f"Deck card {doc_id} missing for first time, starting grace period"
+                    )
+                    _potentially_deleted[doc_key] = current_time
+
+    return queued