bump: version 0.64.3 → 0.64.4

fix(deps): update dependency icalendar to v7

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

@@ -1,89 +0,0 @@
-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

@@ -1,275 +0,0 @@
-# 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

@@ -15,13 +15,13 @@ jobs:
       packages: write
     steps:
       - name: Check out
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
         with:
           fetch-depth: 0
           token: "${{ secrets.PERSONAL_ACCESS_TOKEN }}"
 
       - name: Set up Python
-        uses: actions/setup-python@a26af69be951a213d495a4c3e4e4022e16d87065 # v5
+        uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6.2.0
         with:
           python-version: '3.11'
 
@@ -71,7 +71,7 @@ jobs:
             fi
           }
 
-          # Bump MCP server (default - all commits except helm/astrolabe scopes)
+          # Bump MCP server (default - all commits except helm scope)
           echo "Checking MCP server for version bump..."
 
           # Get the most recent MCP tag
@@ -83,33 +83,36 @@ jobs:
             commit_range="${last_mcp_tag}..HEAD"
           fi
 
-          # Count conventional commits that are NOT scoped to helm or astrolabe
+          # Count conventional commits that are NOT scoped to helm
           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)
+            { grep -v "(helm)" || true; } | wc -l)
 
+          MCP_BUMPED=false
           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"
+            MCP_BUMPED=true
           else
             echo "No commits found for MCP server since $last_mcp_tag"
           fi
 
-          # Bump Helm chart (scope: helm)
+          # Bump Helm chart (scope: helm OR when MCP appVersion changes)
           echo "Checking Helm chart for version bump..."
+          HELM_HAS_COMMITS=false
           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"
+            HELM_HAS_COMMITS=true
           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="$BUMPED_COMPONENTS astrolabe"
+          if [ "$HELM_HAS_COMMITS" = true ]; then
+            echo "Bumping Helm chart version (helm-scoped commits)..."
+            ./scripts/bump-helm.sh
+            BUMPED_COMPONENTS="$BUMPED_COMPONENTS helm"
+          elif [ "$MCP_BUMPED" = true ]; then
+            echo "Bumping Helm chart version (appVersion changed)..."
+            ./scripts/bump-helm.sh --increment PATCH
+            BUMPED_COMPONENTS="$BUMPED_COMPONENTS helm"
           fi
 
           # Output summary
@@ -147,10 +150,6 @@ jobs:
                   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
 

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

@@ -27,15 +27,16 @@ jobs:
 
     steps:
       - name: Checkout repository
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
         with:
           fetch-depth: 1
 
       - name: Run Claude Code Review
         id: claude-review
-        uses: anthropics/claude-code-action@d7b6d50442a89f005016e778bf825a72ef582525 # v1
+        uses: anthropics/claude-code-action@ade221fd1c400376a4799977d683a4eda09f9d7c # v1.0.60
         with:
           claude_code_oauth_token: ${{ secrets.CLAUDE_CODE_OAUTH_TOKEN }}
+          allowed_bots: "renovate-bot-cbcoutinho"
           prompt: |
             REPO: ${{ github.repository }}
             PR NUMBER: ${{ github.event.pull_request.number }}

.github/workflows/claude.yml

@@ -26,13 +26,13 @@ jobs:
       actions: read # Required for Claude to read CI results on PRs
     steps:
       - name: Checkout repository
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
         with:
           fetch-depth: 1
 
       - name: Run Claude Code
         id: claude
-        uses: anthropics/claude-code-action@d7b6d50442a89f005016e778bf825a72ef582525 # v1
+        uses: anthropics/claude-code-action@ade221fd1c400376a4799977d683a4eda09f9d7c # v1.0.60
         with:
           claude_code_oauth_token: ${{ secrets.CLAUDE_CODE_OAUTH_TOKEN }}
 

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

@@ -13,11 +13,11 @@ jobs:
       packages: write
     steps:
       - name: Checkout repository
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Docker meta
         id: meta
-        uses: docker/metadata-action@c299e40c65443455700f0fdfc63efafe5b349051 # v5
+        uses: docker/metadata-action@c299e40c65443455700f0fdfc63efafe5b349051 # v5.10.0
         with:
           # list of Docker images to use as base name for tags
           images: |
@@ -34,18 +34,18 @@ jobs:
             type=raw,value=latest,enable={{is_default_branch}}
 
       - name: Set up Docker Buildx
-        uses: docker/setup-buildx-action@8d2750c68a42422c14e847fe6c8ac0403b4cbd6f # v3
+        uses: docker/setup-buildx-action@8d2750c68a42422c14e847fe6c8ac0403b4cbd6f # v3.12.0
 
       - name: Log in to GitHub Container Registry
         if: github.event_name != 'pull_request'
-        uses: docker/login-action@5e57cd118135c172c3672efd75eb46360885c0ef # v3
+        uses: docker/login-action@c94ce9fb468520275223c153574b00df6fe4bcc9 # v3.7.0
         with:
           registry: ghcr.io
           username: ${{ github.actor }}
           password: ${{ secrets.GITHUB_TOKEN }}
 
       - name: Build and push Docker image
-        uses: docker/build-push-action@263435318d21b8e681c14492fe198d362a7d2c83 # v6
+        uses: docker/build-push-action@10e90e3645eae34f1e60eeb005ba3a3d33f178e8 # v6.19.2
         with:
           push: ${{ github.event_name != 'pull_request' }}
           tags: ${{ steps.meta.outputs.tags }}

.github/workflows/helm-release.yml

@@ -4,6 +4,7 @@ on:
   push:
     tags:
       - v*
+      - nextcloud-mcp-server-*
 
 jobs:
   release:
@@ -14,7 +15,7 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
         with:
           fetch-depth: 0
 

.github/workflows/rag-evaluation.yml

@@ -24,10 +24,10 @@ jobs:
       models: read
 
     steps:
-      - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
 
       - name: Run docker compose with vector sync
-        uses: hoverkraft-tech/compose-action@248470ecc5ed40d8ed3d4480d8260d77179ef579 # v2.4.2
+        uses: hoverkraft-tech/compose-action@4894d2492015c1774ee5a13a95b1072093087ec3 # v2.5.0
         with:
           compose-file: |
             ./docker-compose.yml
@@ -42,7 +42,7 @@ jobs:
           VECTOR_SYNC_SCAN_INTERVAL: "5"
 
       - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
+        uses: astral-sh/setup-uv@eac588ad8def6316056a12d4907a9d4d84ff7a3b # v7.3.0
 
       - name: Wait for Nextcloud to be ready
         run: |
@@ -97,7 +97,7 @@ jobs:
 
       - name: Upload test results
         if: always()
-        uses: actions/upload-artifact@330a01c490aca151604b8cf639adc76d48f6c5d4 # v5
+        uses: actions/upload-artifact@b7c566a772e6b6bfb58ed0dc250532a479d7789f # v6.0.0
         with:
           name: rag-evaluation-results
           path: |

.github/workflows/release.yml

@@ -18,9 +18,9 @@ jobs:
       contents: read
     steps:
       - name: Checkout
-        uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
+        uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
       - name: Install uv
-        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
+        uses: astral-sh/setup-uv@eac588ad8def6316056a12d4907a9d4d84ff7a3b # v7.3.0
       - 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@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
       - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
+        uses: astral-sh/setup-uv@eac588ad8def6316056a12d4907a9d4d84ff7a3b # v7.3.0
       - name: Check format
         run: |
           uv run --frozen ruff format --diff
@@ -27,7 +27,7 @@ jobs:
     runs-on: ubuntu-latest
 
     steps:
-      - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
         with:
           submodules: 'true'
 
@@ -35,7 +35,7 @@ jobs:
       ###### Required to build OIDC App ######
 
       - name: Set up php 8.4
-        uses: shivammathur/setup-php@44454db4f0199b8b9685a5d763dc37cbf79108e1 # v2
+        uses: shivammathur/setup-php@44454db4f0199b8b9685a5d763dc37cbf79108e1 # 2.36.0
         with:
           php-version: 8.4
           coverage: none
@@ -48,32 +48,15 @@ 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@248470ecc5ed40d8ed3d4480d8260d77179ef579 # v2.4.2
+        uses: hoverkraft-tech/compose-action@4894d2492015c1774ee5a13a95b1072093087ec3 # v2.5.0
         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@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
+        uses: astral-sh/setup-uv@eac588ad8def6316056a12d4907a9d4d84ff7a3b # v7.3.0
 
       - name: Install Playwright dependencies
         run: |

.gitmodules

@@ -4,3 +4,6 @@
 [submodule "third_party/notes"]
 	path = third_party/notes
 	url = https://github.com/cbcoutinho/notes
+[submodule "third_party/astrolabe"]
+	path = third_party/astrolabe
+	url = https://github.com/cbcoutinho/astrolabe

CHANGELOG.md

@@ -5,6 +5,265 @@ 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/).
 
+## v0.64.4 (2026-02-26)
+
+### Fix
+
+- **deps**: update dependency icalendar to v7
+
+## v0.64.3 (2026-02-21)
+
+### Fix
+
+- address PR #574 fourth review round
+- address PR #574 third review round
+- address PR #574 second review round
+- address PR #574 review comments
+- wrap raw list returns in response models to produce single TextContent block
+
+## v0.64.2 (2026-02-20)
+
+### Fix
+
+- address PR #571 review comments
+- resolve stale credentials causing astrolabe background sync test failures
+
+### Refactor
+
+- enforce PLC0415 (import-outside-top-level) for source code
+
+## v0.64.1 (2026-02-18)
+
+### Fix
+
+- **deps**: update dependency mcp to >=1.26,<1.27
+
+## v0.64.0 (2026-02-16)
+
+### Feat
+
+- add self-signed SSL certificate support for Nextcloud connections
+
+### Fix
+
+- add type: ignore for caldav ssl_verify_cert parameter
+- convert CA bundle path to ssl.SSLContext to avoid httpx deprecation warning
+
+## v0.63.5 (2026-02-16)
+
+### Refactor
+
+- remove stale astrolabe references from commitizen config
+- extract Astrolabe to separate repository
+
+## v0.63.4 (2026-02-08)
+
+### Fix
+
+- strip whitespace from category names when splitting
+- handle categories, recurrence_rule, attendees, and reminder_minutes in update_event
+
+## v0.63.3 (2026-02-08)
+
+### Fix
+
+- expand recurring events in date-range queries
+
+## v0.63.2 (2026-02-07)
+
+### Fix
+
+- use CalDAV time-range filter for calendar date range queries
+
+## v0.63.1 (2026-02-03)
+
+### Fix
+
+- **helm**: add backward compatibility for legacy persistence configs
+
+## v0.63.0 (2026-01-28)
+
+### Feat
+
+- **astrolabe**: add background token refresh job
+
+### Fix
+
+- **astrolabe**: add pagination and psalm fixes for token refresh
+- **astrolabe**: add locking to prevent token refresh race condition
+- **astrolabe**: add issued_at to on-demand token refresh
+
+## v0.62.0 (2026-01-26)
+
+### Feat
+
+- **scripts**: add database query helpers for development
+
+### Fix
+
+- **astrolabe**: resolve Psalm type errors in PDF preview code
+- **astrolabe**: fix Psalm baseline and ESLint import order
+- **astrolabe**: load pdfjs-dist externally to fix PDF viewer
+- **astrolabe**: improve error messages for authorization issues
+- **astrolabe**: rename OAuthController and fix app password check
+- **tests**: improve Astrolabe integration test reliability
+- **astrolabe**: update Plotly title attributes for v3 compatibility
+- **deps**: update dependency plotly.js-dist-min to v3
+
+### Refactor
+
+- **api**: split management.py into domain-focused modules
+- **astrolabe**: replace client-side PDF.js with server-side PyMuPDF rendering
+
+## v0.61.5 (2026-01-17)
+
+### Fix
+
+- **astrolabe**: improve token refresh error handling and validation
+- **astrolabe**: delete stale tokens when refresh fails
+- **astrolabe**: resolve CI failures for code quality checks
+- **astrolabe**: use internal URL for OAuth token refresh
+
+### Refactor
+
+- **astrolabe**: add PHP property types to fix Psalm errors
+- **astrolabe**: upgrade to @nextcloud/vue 9.3.3 API
+
+## v0.61.4 (2026-01-16)
+
+### Fix
+
+- **astrolabe**: Address reviewer feedback for hybrid mode
+- **astrolabe**: Fix NcSelect options and CSS loading
+- **astrolabe**: fix OAuth flow and settings UI for hybrid mode
+- **api**: return OIDC config in hybrid mode for Astrolabe OAuth flow
+
+## v0.61.3 (2026-01-15)
+
+### Fix
+
+- **astrolabe**: address review feedback for Vue 3 bindings
+- **astrolabe**: update Vue component bindings for Vue 3 compatibility
+
+## v0.61.2 (2026-01-15)
+
+### Fix
+
+- **ci**: bump helm chart version when MCP appVersion changes
+
+## v0.61.1 (2026-01-15)
+
+### Fix
+
+- **astrolabe**: define appName and appVersion for @nextcloud/vue
+
+## v0.61.0 (2026-01-14)
+
+### Feat
+
+- Add rate limiting and extract helpers for app password endpoints
+
+### Fix
+
+- Add missing annotations for deck remove/unassign operations
+- **auth**: Store app passwords locally for multi-user BasicAuth background sync
+
+### Refactor
+
+- Use get_settings() for vector sync enabled check
+- Extract storage helper and improve PHP error handling
+
+## v0.60.4 (2026-01-12)
+
+### Fix
+
+- **deck**: use correct endpoint for reorder_card to fix cross-stack moves
+
+## v0.60.3 (2025-12-31)
+
+### Fix
+
+- **deck**: Always preserve fields in update_card for partial updates
+- **astrolabe**: Fix CSS loading for Nextcloud apps
+- **astrolabe**: Fix revoke access button HTTP method mismatch
+
+## v0.60.2 (2025-12-29)
+
+### Fix
+
+- **oauth**: Enable browser OAuth routes for Management API in hybrid mode
+
+## v0.60.1 (2025-12-26)
+
+### Fix
+
+- **mcp**: Move all imports to the top of modules
+
+## v0.60.0 (2025-12-26)
+
+### Feat
+
+- Remove URL rewriting in favor of proper nextcloud config
+- **helm**: migrate to new environment variable naming convention
+- Migrate to vue 3
+- **astrolabe**: upgrade to Vue 3 and @nextcloud/vue 9
+
+### Fix
+
+- **tests**: Add singleton reset fixture to prevent anyio.WouldBlock errors
+- **tests**: Fix integration test failures in qdrant, sampling, and rag tests
+- **auth**: Skip issuer validation for management API tokens
+- Use settings.enable_offline_access for env var consolidation
+- Add required config.py attributes
+- **docker**: remove overwritehost to fix container-to-container DCR
+- **deps**: update dependency @nextcloud/vue to v9
+- **deps**: update dependency vue to v3
+
+### Refactor
+
+- **auth**: Decouple BasicAuth and OAuth authentication strategies
+
+## v0.59.1 (2025-12-22)
+
+### Fix
+
+- **helm**: set OIDC client env vars when using existingSecret
+- **helm**: trigger chart release workflow on helm chart tags
+
+## v0.59.0 (2025-12-22)
+
+### Feat
+
+- **helm**: add support for multi-user BasicAuth mode
+
+### Fix
+
+- **helm**: address PR #447 reviewer feedback
+- **helm**: include MCP server version bumps in changelog pattern
+
+## v0.58.0 (2025-12-22)
+
+### Feat
+
+- **config**: enable DCR for multi-user BasicAuth with offline access
+- **astrolabe**: implement app password provisioning for multi-user background sync
+- **config**: consolidate configuration with smart dependency resolution (ADR-021)
+
+## 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

CLAUDE.md

@@ -239,6 +239,25 @@ uv run python -m tests.load.benchmark --output results.json --verbose
 
 **Credentials**: root/password, nextcloud/password, database: `nextcloud`
 
+### Quick Query Script (Recommended for Agents)
+
+Use `scripts/dbquery.py` for single SQL statements without requiring approval for each `docker compose exec`:
+
+```bash
+# Basic query
+./scripts/dbquery.py "SELECT COUNT(*) FROM oc_users"
+
+# Vertical output (one column per line) - useful for wide tables
+./scripts/dbquery.py -E "SELECT * FROM oc_oidc_clients LIMIT 1"
+
+# With different credentials
+./scripts/dbquery.py -u nextcloud -p nextcloud "SHOW TABLES"
+```
+
+### Direct Docker Access
+
+For interactive sessions or complex operations:
+
 ```bash
 # Connect to database
 docker compose exec db mariadb -u root -ppassword nextcloud
@@ -264,6 +283,40 @@ docker compose exec db mariadb -u root -ppassword nextcloud -e \
 - `oc_oidc_registration_tokens` - RFC 7592 registration tokens
 - `oc_oidc_redirect_uris` - Redirect URIs
 
+### SQLite Databases (MCP Services)
+
+Use `scripts/sqlitequery.py` to query SQLite databases in MCP service containers:
+
+```bash
+# List tables
+./scripts/sqlitequery.py ".tables"
+
+# Query specific service
+./scripts/sqlitequery.py -s oauth "SELECT * FROM refresh_tokens"
+./scripts/sqlitequery.py -s keycloak "SELECT * FROM oauth_clients"
+./scripts/sqlitequery.py -s basic "SELECT * FROM app_passwords"
+
+# With column headers
+./scripts/sqlitequery.py --column "SELECT * FROM audit_logs LIMIT 5"
+
+# JSON output
+./scripts/sqlitequery.py --json "SELECT * FROM oauth_sessions"
+
+# View schema
+./scripts/sqlitequery.py -s oauth ".schema refresh_tokens"
+```
+
+**Services**: `mcp` (default), `oauth`, `keycloak`, `basic`
+
+**SQLite Tables**:
+- `refresh_tokens` - OAuth refresh tokens with user profiles
+- `audit_logs` - Security audit trail
+- `oauth_clients` - DCR OAuth client credentials
+- `oauth_sessions` - OAuth flow session state
+- `registered_webhooks` - Webhook registrations
+- `app_passwords` - Multi-user BasicAuth passwords
+- `alembic_version` - Migration tracking
+
 ## Architecture Quick Reference
 
 **For detailed architecture, see:**

CONTRIBUTING.md

@@ -2,7 +2,7 @@
 
 ## Version Management
 
-This monorepo uses commitizen for version management with **independent versioning** for three components:
+This monorepo uses commitizen for version management with **independent versioning** for two components:
 
 ### Components
 
@@ -10,7 +10,8 @@ This monorepo uses commitizen for version management with **independent versioni
 |-----------|-------|--------------|-------------|
 | 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` |
+
+> **Note:** The Astrolabe Nextcloud app has been moved to its own repository at [cbcoutinho/astrolabe](https://github.com/cbcoutinho/astrolabe).
 
 ### Commit Message Format
 
@@ -24,10 +25,6 @@ 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:
@@ -40,7 +37,6 @@ feat: add new feature  # → MCP server (v0.54.0)
 #### 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"
 ```
@@ -58,10 +54,6 @@ git commit -m "feat(mcp): add calendar sync"
 # → 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
@@ -76,7 +68,6 @@ 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
 
@@ -101,7 +92,6 @@ uv run cz --config .cz.toml bump --increment MINOR
 
 - **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
 

Dockerfile

@@ -1,6 +1,6 @@
-FROM docker.io/library/python:3.12-slim-trixie@sha256:fa48eefe2146644c2308b909d6bb7651a768178f84fc9550dcd495e4d6d84d01
+FROM docker.io/library/python:3.12-slim-trixie@sha256:39e4e1ccb01578e3c86f7a0cf7b7fd89b8dbe2c27a88de11cf726ba669469f49
 
-COPY --from=ghcr.io/astral-sh/uv:0.9.18@sha256:5713fa8217f92b80223bc83aac7db36ec80a84437dbc0d04bbc659cae030d8c9 /uv /uvx /bin/
+COPY --from=ghcr.io/astral-sh/uv:0.10.6@sha256:2f2ccd27bbf953ec7a9e3153a4563705e41c852a5e1912b438fc44d88d6cb52c /uv /uvx /bin/
 
 # Install dependencies
 # 1. git (required for caldav dependency from git)

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:fa48eefe2146644c2308b909d6bb7651a768178f84fc9550dcd495e4d6d84d01
+FROM docker.io/library/python:3.12-slim-trixie@sha256:39e4e1ccb01578e3c86f7a0cf7b7fd89b8dbe2c27a88de11cf726ba669469f49
 
 WORKDIR /app
 
 # Install uv for fast dependency management
-COPY --from=ghcr.io/astral-sh/uv:0.9.18@sha256:5713fa8217f92b80223bc83aac7db36ec80a84437dbc0d04bbc659cae030d8c9 /uv /uvx /bin/
+COPY --from=ghcr.io/astral-sh/uv:0.10.6@sha256:2f2ccd27bbf953ec7a9e3153a4563705e41c852a5e1912b438fc44d88d6cb52c /uv /uvx /bin/
 
 # Install dependencies
 # 1. git (required for caldav dependency from git)

README.md

@@ -99,7 +99,7 @@ Want to see another Nextcloud app supported? [Open an issue](https://github.com/
 
 ### Authentication Modes
 
-The server supports two authentication modes:
+The server supports three authentication modes:
 
 **Single-User Mode (BasicAuth):**
 - One set of credentials shared by all MCP clients
@@ -113,6 +113,12 @@ The server supports two authentication modes:
 - More secure: tokens expire, credentials never shared with server
 - Best for: Teams, multi-user deployments, production environments with multiple users
 
+**Hybrid Mode (Multi-User BasicAuth + OAuth):**
+- MCP clients use BasicAuth (simple, stateless)
+- Admin operations use OAuth (webhooks, background sync)
+- Best for: Nextcloud deployments with admin-managed webhooks and semantic search
+- Requires: `ENABLE_MULTI_USER_BASIC_AUTH=true` + `ENABLE_OFFLINE_ACCESS=true`
+
 See [docs/authentication.md](docs/authentication.md) for detailed setup instructions.
 
 ## Semantic Search
@@ -127,7 +133,7 @@ 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

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

@@ -4,8 +4,8 @@ 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"
+# Set overwrite.cli.url to the external URL for OIDC discovery
+# This ensures OAuth flows redirect to the correct external URL
+# Important: The Astrolabe OAuth controller makes internal HTTP requests to /.well-known/openid-configuration
+# which needs to return URLs reachable by external browsers (localhost:8080, not localhost:80)
 php /var/www/html/occ config:system:set overwrite.cli.url --value="http://localhost:8080"

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

@@ -2,35 +2,17 @@
 
 set -euox pipefail
 
-echo "Installing Astrolabe app for testing..."
+echo "Installing Astrolabe app from app store..."
 
-# 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
+if [ -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 "Astrolabe app installed successfully"
 echo ""
 echo "Note: MCP server configuration is managed dynamically during tests"
 echo "      to support testing multiple MCP server deployments."

app-hooks/post-installation/25-configure-mcp-server-url.sh

@@ -0,0 +1,16 @@
+#!/bin/bash
+# Configure MCP server URL for Astrolabe background sync
+# This URL is used by Astrolabe to send app passwords to the MCP server
+
+set -e
+
+# The MCP multi-user BasicAuth service runs on port 8000 inside the container
+# From Nextcloud's perspective (inside Docker network), we reach it via service name
+MCP_SERVER_URL="${MCP_SERVER_URL:-http://mcp-multi-user-basic:8000}"
+
+echo "Configuring MCP server URL: $MCP_SERVER_URL"
+
+# Set the mcp_server_url in config.php via occ
+php occ config:system:set mcp_server_url --value="$MCP_SERVER_URL"
+
+echo "MCP server URL configured successfully"

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

@@ -1,6 +1,6 @@
 [tool.commitizen]
 name = "cz_conventional_commits"
-version = "0.54.0"
+version = "0.57.85"
 tag_format = "nextcloud-mcp-server-$version"
 version_scheme = "semver"
 update_changelog_on_bump = true
@@ -18,7 +18,8 @@ ignored_tag_formats = [
 ]
 
 # 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\\)(!)?:"
+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

@@ -14,6 +14,394 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Configurable resource limits
 - Grafana dashboard annotations
 
+## nextcloud-mcp-server-0.57.85 (2026-02-25)
+
+## nextcloud-mcp-server-0.57.84 (2026-02-25)
+
+## nextcloud-mcp-server-0.57.83 (2026-02-25)
+
+## nextcloud-mcp-server-0.57.82 (2026-02-25)
+
+## nextcloud-mcp-server-0.57.81 (2026-02-25)
+
+## nextcloud-mcp-server-0.57.80 (2026-02-24)
+
+## nextcloud-mcp-server-0.57.79 (2026-02-24)
+
+## nextcloud-mcp-server-0.57.78 (2026-02-24)
+
+## nextcloud-mcp-server-0.57.77 (2026-02-24)
+
+## nextcloud-mcp-server-0.57.76 (2026-02-24)
+
+## nextcloud-mcp-server-0.57.75 (2026-02-23)
+
+## nextcloud-mcp-server-0.57.74 (2026-02-21)
+
+## nextcloud-mcp-server-0.57.73 (2026-02-21)
+
+### Fix
+
+- address PR #574 fourth review round
+- address PR #574 third review round
+- address PR #574 second review round
+- address PR #574 review comments
+- wrap raw list returns in response models to produce single TextContent block
+
+## nextcloud-mcp-server-0.57.72 (2026-02-20)
+
+## nextcloud-mcp-server-0.57.71 (2026-02-20)
+
+## nextcloud-mcp-server-0.57.70 (2026-02-20)
+
+### Fix
+
+- address PR #571 review comments
+- resolve stale credentials causing astrolabe background sync test failures
+
+### Refactor
+
+- enforce PLC0415 (import-outside-top-level) for source code
+
+## nextcloud-mcp-server-0.57.69 (2026-02-20)
+
+## nextcloud-mcp-server-0.57.68 (2026-02-19)
+
+## nextcloud-mcp-server-0.57.67 (2026-02-19)
+
+## nextcloud-mcp-server-0.57.66 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.65 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.64 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.63 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.62 (2026-02-18)
+
+### Fix
+
+- **deps**: update dependency mcp to >=1.26,<1.27
+
+## nextcloud-mcp-server-0.57.61 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.60 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.59 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.58 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.57 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.56 (2026-02-18)
+
+## nextcloud-mcp-server-0.57.55 (2026-02-17)
+
+## nextcloud-mcp-server-0.57.54 (2026-02-17)
+
+## nextcloud-mcp-server-0.57.53 (2026-02-17)
+
+## nextcloud-mcp-server-0.57.52 (2026-02-17)
+
+## nextcloud-mcp-server-0.57.51 (2026-02-16)
+
+### Feat
+
+- add self-signed SSL certificate support for Nextcloud connections
+
+### Fix
+
+- add type: ignore for caldav ssl_verify_cert parameter
+- convert CA bundle path to ssl.SSLContext to avoid httpx deprecation warning
+
+## nextcloud-mcp-server-0.57.50 (2026-02-16)
+
+## nextcloud-mcp-server-0.57.49 (2026-02-16)
+
+### Refactor
+
+- remove stale astrolabe references from commitizen config
+- extract Astrolabe to separate repository
+
+## nextcloud-mcp-server-0.57.48 (2026-02-15)
+
+## nextcloud-mcp-server-0.57.47 (2026-02-15)
+
+## nextcloud-mcp-server-0.57.46 (2026-02-12)
+
+## nextcloud-mcp-server-0.57.45 (2026-02-12)
+
+## nextcloud-mcp-server-0.57.44 (2026-02-11)
+
+## nextcloud-mcp-server-0.57.43 (2026-02-11)
+
+## nextcloud-mcp-server-0.57.42 (2026-02-08)
+
+### Fix
+
+- strip whitespace from category names when splitting
+- handle categories, recurrence_rule, attendees, and reminder_minutes in update_event
+
+## nextcloud-mcp-server-0.57.41 (2026-02-08)
+
+### Fix
+
+- expand recurring events in date-range queries
+
+## nextcloud-mcp-server-0.57.40 (2026-02-07)
+
+### Fix
+
+- use CalDAV time-range filter for calendar date range queries
+
+## nextcloud-mcp-server-0.57.39 (2026-02-07)
+
+## nextcloud-mcp-server-0.57.38 (2026-02-07)
+
+## nextcloud-mcp-server-0.57.37 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.36 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.35 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.34 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.33 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.32 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.31 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.30 (2026-02-06)
+
+## nextcloud-mcp-server-0.57.29 (2026-02-04)
+
+## nextcloud-mcp-server-0.57.28 (2026-02-03)
+
+## nextcloud-mcp-server-0.57.27 (2026-02-03)
+
+### Fix
+
+- **helm**: add backward compatibility for legacy persistence configs
+
+## nextcloud-mcp-server-0.57.26 (2026-01-31)
+
+## nextcloud-mcp-server-0.57.25 (2026-01-31)
+
+## nextcloud-mcp-server-0.57.24 (2026-01-31)
+
+## nextcloud-mcp-server-0.57.23 (2026-01-30)
+
+## nextcloud-mcp-server-0.57.22 (2026-01-30)
+
+## nextcloud-mcp-server-0.57.21 (2026-01-30)
+
+## nextcloud-mcp-server-0.57.20 (2026-01-29)
+
+## nextcloud-mcp-server-0.57.19 (2026-01-28)
+
+## nextcloud-mcp-server-0.57.18 (2026-01-28)
+
+## nextcloud-mcp-server-0.57.17 (2026-01-28)
+
+## nextcloud-mcp-server-0.57.16 (2026-01-28)
+
+### Feat
+
+- **astrolabe**: add background token refresh job
+
+### Fix
+
+- **astrolabe**: add pagination and psalm fixes for token refresh
+- **astrolabe**: add locking to prevent token refresh race condition
+- **astrolabe**: add issued_at to on-demand token refresh
+
+## nextcloud-mcp-server-0.57.15 (2026-01-26)
+
+### Feat
+
+- **scripts**: add database query helpers for development
+
+### Fix
+
+- **astrolabe**: resolve Psalm type errors in PDF preview code
+- **astrolabe**: fix Psalm baseline and ESLint import order
+- **astrolabe**: load pdfjs-dist externally to fix PDF viewer
+- **astrolabe**: improve error messages for authorization issues
+- **astrolabe**: rename OAuthController and fix app password check
+- **tests**: improve Astrolabe integration test reliability
+- **astrolabe**: update Plotly title attributes for v3 compatibility
+- **deps**: update dependency plotly.js-dist-min to v3
+
+### Refactor
+
+- **api**: split management.py into domain-focused modules
+- **astrolabe**: replace client-side PDF.js with server-side PyMuPDF rendering
+
+## nextcloud-mcp-server-0.57.14 (2026-01-26)
+
+## nextcloud-mcp-server-0.57.13 (2026-01-24)
+
+## nextcloud-mcp-server-0.57.12 (2026-01-20)
+
+## nextcloud-mcp-server-0.57.11 (2026-01-20)
+
+## nextcloud-mcp-server-0.57.10 (2026-01-19)
+
+## nextcloud-mcp-server-0.57.9 (2026-01-19)
+
+## nextcloud-mcp-server-0.57.8 (2026-01-18)
+
+## nextcloud-mcp-server-0.57.7 (2026-01-17)
+
+### Fix
+
+- **astrolabe**: improve token refresh error handling and validation
+- **astrolabe**: delete stale tokens when refresh fails
+- **astrolabe**: resolve CI failures for code quality checks
+- **astrolabe**: use internal URL for OAuth token refresh
+
+### Refactor
+
+- **astrolabe**: add PHP property types to fix Psalm errors
+- **astrolabe**: upgrade to @nextcloud/vue 9.3.3 API
+
+## nextcloud-mcp-server-0.57.6 (2026-01-16)
+
+## nextcloud-mcp-server-0.57.5 (2026-01-16)
+
+## nextcloud-mcp-server-0.57.4 (2026-01-16)
+
+### Fix
+
+- **astrolabe**: Address reviewer feedback for hybrid mode
+- **astrolabe**: Fix NcSelect options and CSS loading
+- **astrolabe**: fix OAuth flow and settings UI for hybrid mode
+- **api**: return OIDC config in hybrid mode for Astrolabe OAuth flow
+
+## nextcloud-mcp-server-0.57.3 (2026-01-15)
+
+## nextcloud-mcp-server-0.57.2 (2026-01-15)
+
+### Fix
+
+- **astrolabe**: address review feedback for Vue 3 bindings
+- **astrolabe**: update Vue component bindings for Vue 3 compatibility
+
+## nextcloud-mcp-server-0.57.1 (2026-01-15)
+
+### Fix
+
+- **ci**: bump helm chart version when MCP appVersion changes
+- **astrolabe**: define appName and appVersion for @nextcloud/vue
+
+## nextcloud-mcp-server-0.57.0 (2026-01-15)
+
+### Feat
+
+- Add rate limiting and extract helpers for app password endpoints
+
+### Fix
+
+- Add missing annotations for deck remove/unassign operations
+- **auth**: Store app passwords locally for multi-user BasicAuth background sync
+- **deck**: use correct endpoint for reorder_card to fix cross-stack moves
+- **deck**: Always preserve fields in update_card for partial updates
+- **astrolabe**: Fix CSS loading for Nextcloud apps
+- **astrolabe**: Fix revoke access button HTTP method mismatch
+
+### Refactor
+
+- Use get_settings() for vector sync enabled check
+- Extract storage helper and improve PHP error handling
+
+## nextcloud-mcp-server-0.56.2 (2025-12-29)
+
+### Fix
+
+- **oauth**: Enable browser OAuth routes for Management API in hybrid mode
+
+## nextcloud-mcp-server-0.56.1 (2025-12-26)
+
+### Fix
+
+- **mcp**: Move all imports to the top of modules
+
+## nextcloud-mcp-server-0.56.0 (2025-12-26)
+
+### Feat
+
+- Remove URL rewriting in favor of proper nextcloud config
+- **helm**: migrate to new environment variable naming convention
+- Migrate to vue 3
+- **astrolabe**: upgrade to Vue 3 and @nextcloud/vue 9
+
+### Fix
+
+- **tests**: Add singleton reset fixture to prevent anyio.WouldBlock errors
+- **tests**: Fix integration test failures in qdrant, sampling, and rag tests
+- **auth**: Skip issuer validation for management API tokens
+- Use settings.enable_offline_access for env var consolidation
+- Add required config.py attributes
+- **docker**: remove overwritehost to fix container-to-container DCR
+- **deps**: update dependency @nextcloud/vue to v9
+- **deps**: update dependency vue to v3
+
+### Refactor
+
+- **auth**: Decouple BasicAuth and OAuth authentication strategies
+
+## nextcloud-mcp-server-0.55.2 (2025-12-22)
+
+### Fix
+
+- **helm**: set OIDC client env vars when using existingSecret
+
+## nextcloud-mcp-server-0.55.1 (2025-12-22)
+
+### Fix
+
+- **helm**: trigger chart release workflow on helm chart tags
+
+## nextcloud-mcp-server-0.55.0 (2025-12-22)
+
+### BREAKING CHANGE
+
+- MCP server now bumps for ANY conventional commit except
+those explicitly scoped to helm or astrolabe.
+
+### Feat
+
+- **helm**: add support for multi-user BasicAuth mode
+- **config**: enable DCR for multi-user BasicAuth with offline access
+- **astrolabe**: implement app password provisioning for multi-user background sync
+- **config**: consolidate configuration with smart dependency resolution (ADR-021)
+- **auth**: add multi-user BasicAuth pass-through mode
+- **astrolabe**: add dynamic MCP server configuration for testing
+- **ci**: add --increment flag to bump scripts for manual version control
+
+### Fix
+
+- **helm**: address PR #447 reviewer feedback
+- **helm**: include MCP server version bumps in changelog pattern
+- **config**: address reviewer feedback
+- **astrolabe**: screenshots in info.xml
+- **astrolabe**: screenshots in info.xml
+- **astrolabe**: Update screenshots
+- **ci**: skip existing Helm chart releases to prevent duplicate release errors
+- **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
+- **ci**: push all tags explicitly in bump workflow
+- **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
+
+### Refactor
+
+- **config**: centralize configuration validation and simplify startup
+
 ## nextcloud-mcp-server-0.54.0 (2025-12-19)
 
 ### Feat

charts/nextcloud-mcp-server/Chart.lock

@@ -1,9 +1,9 @@
 dependencies:
 - name: qdrant
   repository: https://qdrant.github.io/qdrant-helm
-  version: 1.16.2
+  version: 1.17.0
 - name: ollama
   repository: https://otwld.github.io/ollama-helm
-  version: 1.36.0
-digest: sha256:fab8008217b27ff4e3e139c2f481eedaa23f9f64a3a086d0e9deea2195b69b63
-generated: "2025-12-14T11:07:07.024787592Z"
+  version: 1.45.0
+digest: sha256:a325b7093a64921fb5c6648c19c31a61799c8b279da21f08b9e892a9e5a37227
+generated: "2026-02-23T05:14:08.147145912Z"

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: 0.54.0
-appVersion: "0.56.2"
+version: 0.57.85
+appVersion: "0.64.4"
 keywords:
   - nextcloud
   - mcp
@@ -27,10 +27,10 @@ annotations:
   grafana_dashboard_folder: "Nextcloud MCP"
 dependencies:
   - name: qdrant
-    version: "1.16.2"
+    version: "1.17.0"
     repository: https://qdrant.github.io/qdrant-helm
     condition: qdrant.networkMode.deploySubchart
   - name: ollama
-    version: "1.36.0"
+    version: "1.45.0"
     repository: https://otwld.github.io/ollama-helm
     condition: ollama.enabled

charts/nextcloud-mcp-server/README.md

@@ -99,11 +99,11 @@ ingress:
 |-----------|-------------|---------|
 | `nextcloud.host` | URL of your Nextcloud instance (required) | `""` |
 | `nextcloud.mcpServerUrl` | MCP server URL for OAuth callbacks (OAuth only, optional) | Smart default* |
-| `nextcloud.publicIssuerUrl` | Public issuer URL for OAuth (OAuth only, optional) | Smart default** |
+| `nextcloud.publicIssuerUrl` | Public URL for browser-accessible OAuth authorization endpoint (OAuth only, optional) | Smart default** |
 
 **Smart Defaults:**
 - `*mcpServerUrl`: If not set, automatically uses ingress host (if enabled) or `http://localhost:8000` (for port-forward setups)
-- `**publicIssuerUrl`: If not set, automatically defaults to `nextcloud.host` (which works when both clients and MCP server access Nextcloud at the same URL)
+- `**publicIssuerUrl`: If not set, defaults to `nextcloud.host`. **Only used for authorization endpoints** that browsers must access. All server-to-server endpoints (token, JWKS, introspection, userinfo) use URLs from OIDC discovery without rewriting
 
 #### Authentication
 
@@ -118,6 +118,25 @@ ingress:
 | `auth.oauth.persistence.enabled` | Enable persistent storage for OAuth | `true` |
 | `auth.oauth.persistence.size` | Size of OAuth storage PVC | `100Mi` |
 
+#### Data Storage
+
+The `/app/data` directory is used for application data (token databases, Qdrant persistent storage, etc.). It is always mounted as writable to support the read-only root filesystem security context.
+
+| Parameter | Description | Default |
+|-----------|-------------|---------|
+| `dataStorage.enabled` | Enable persistent storage for `/app/data` | `false` |
+| `dataStorage.size` | Size of data storage PVC | `1Gi` |
+| `dataStorage.storageClass` | Storage class (leave empty for default) | `""` |
+| `dataStorage.accessMode` | Access mode | `ReadWriteOnce` |
+| `dataStorage.existingClaim` | Use existing PVC | `""` |
+
+**When to enable persistence:**
+- Multi-user basic auth with offline access (stores `tokens.db`)
+- Qdrant persistent mode (stores vector database)
+- Any feature requiring persistent app data
+
+**When persistence is disabled:** Uses `emptyDir` (non-persistent, data lost on pod restart, but directory remains writable).
+
 #### MCP Server Configuration
 
 | Parameter | Description | Default |
@@ -208,16 +227,16 @@ The application exposes HTTP health check endpoints:
 
 #### Vector Search & Semantic Capabilities (Optional)
 
-Enable semantic search capabilities by deploying a vector database (Qdrant) and embedding service (Ollama or OpenAI).
+Enable semantic search capabilities with BM25 hybrid search by deploying a vector database (Qdrant) and embedding service (Ollama or OpenAI).
 
-**Vector Sync Configuration:**
+**Semantic Search Configuration:**
 
 | Parameter | Description | Default |
 |-----------|-------------|---------|
-| `vectorSync.enabled` | Enable background vector synchronization | `false` |
-| `vectorSync.scanInterval` | Scan interval in seconds | `3600` |
-| `vectorSync.processorWorkers` | Number of concurrent processor workers | `3` |
-| `vectorSync.queueMaxSize` | Maximum queue size for pending documents | `10000` |
+| `semanticSearch.enabled` | Enable semantic search and background vector synchronization | `false` |
+| `semanticSearch.scanInterval` | Scan interval in seconds | `3600` |
+| `semanticSearch.processorWorkers` | Number of concurrent processor workers | `3` |
+| `semanticSearch.queueMaxSize` | Maximum queue size for pending documents | `10000` |
 
 **Document Chunking Configuration:**
 
@@ -427,7 +446,7 @@ nextcloud:
   host: https://cloud.example.com
   # mcpServerUrl and publicIssuerUrl are optional!
   # If not set, mcpServerUrl defaults to ingress host or localhost
-  # publicIssuerUrl defaults to nextcloud.host
+  # publicIssuerUrl defaults to nextcloud.host (only used for browser-accessible auth endpoint)
 
 auth:
   mode: oauth
@@ -459,7 +478,7 @@ This example shows OAuth without pre-registered credentials (using DCR) and opti
 nextcloud:
   host: https://cloud.example.com
   # mcpServerUrl will automatically use ingress host (https://mcp.example.com)
-  # publicIssuerUrl will automatically default to nextcloud.host
+  # publicIssuerUrl will automatically default to nextcloud.host (only used for browser-accessible auth endpoint)
 
 auth:
   mode: oauth
@@ -537,8 +556,8 @@ auth:
     username: admin
     password: secure-password
 
-# Enable vector sync
-vectorSync:
+# Enable semantic search
+semanticSearch:
   enabled: true
   scanInterval: 1800  # Scan every 30 minutes
   processorWorkers: 5
@@ -576,7 +595,7 @@ ollama:
 Or use an external Ollama instance:
 
 ```yaml
-vectorSync:
+semanticSearch:
   enabled: true
 
 qdrant:
@@ -592,7 +611,7 @@ ollama:
 Or use OpenAI for embeddings:
 
 ```yaml
-vectorSync:
+semanticSearch:
   enabled: true
 
 qdrant:
@@ -689,7 +708,9 @@ Readiness (returns 200 if ready, 503 if not ready):
 
 1. **Connection refused to Nextcloud**
    - Verify `nextcloud.host` is accessible from the Kubernetes cluster
+   - For OAuth mode: Ensure MCP server can reach OIDC discovery endpoints (token, JWKS, introspection, userinfo URLs)
    - Check network policies and firewall rules
+   - Note: Do not use internal Docker hostnames (like `http://app:80`) for `nextcloud.host` - use externally resolvable URLs
 
 2. **Authentication failures**
    - For basic auth: verify username/password are correct

charts/nextcloud-mcp-server/templates/NOTES.txt

@@ -69,12 +69,12 @@ Your Nextcloud MCP Server has been deployed in {{ .Values.auth.mode }} authentic
    {{- end }}
 {{- end }}
 
-{{- if .Values.vectorSync.enabled }}
+{{- if .Values.semanticSearch.enabled }}
 
-5. Vector Search & Semantic Capabilities:
-   - Vector Sync: Enabled
-   - Scan Interval: {{ .Values.vectorSync.scanInterval }}s
-   - Processor Workers: {{ .Values.vectorSync.processorWorkers }}
+5. Semantic Search & Vector Capabilities:
+   - Semantic Search: Enabled
+   - Scan Interval: {{ .Values.semanticSearch.scanInterval }}s
+   - Processor Workers: {{ .Values.semanticSearch.processorWorkers }}
    {{- if .Values.qdrant.enabled }}
    - Qdrant: Deployed as subchart ({{ .Release.Name }}-qdrant:6333)
    {{- else }}
@@ -120,6 +120,55 @@ Your Nextcloud MCP Server has been deployed in {{ .Values.auth.mode }} authentic
    The dashboard JSON is available in the chart at charts/nextcloud-mcp-server/dashboards/nextcloud-mcp-server.json
 {{- end }}
 
+{{- $legacyMultiUserBasic := eq (include "nextcloud-mcp-server.legacyMultiUserBasicPersistence" .) "true" }}
+{{- $legacyQdrant := eq (include "nextcloud-mcp-server.legacyQdrantPersistence" .) "true" }}
+{{- if or $legacyMultiUserBasic $legacyQdrant }}
+
+================================================================================
+                         DEPRECATION WARNING
+================================================================================
+
+You are using deprecated persistence configuration that will be removed in a
+future release. Your deployment will continue to work, but please migrate to
+the new unified dataStorage configuration.
+
+Deprecated settings detected:
+{{- if $legacyMultiUserBasic }}
+  - auth.multiUserBasic.persistence.* (currently enabled)
+{{- end }}
+{{- if $legacyQdrant }}
+  - qdrant.localPersistence.* (currently enabled)
+{{- end }}
+
+To migrate, update your values.yaml:
+
+  dataStorage:
+    enabled: true
+{{- if $legacyMultiUserBasic }}
+    size: {{ .Values.auth.multiUserBasic.persistence.size }}
+{{- else if $legacyQdrant }}
+    size: {{ .Values.qdrant.localPersistence.size }}
+{{- end }}
+    # storageClass: ""  # Optional: specify storage class
+    # existingClaim: "" # Optional: use existing PVC to preserve data
+
+After migrating, remove the deprecated settings:
+{{- if $legacyMultiUserBasic }}
+  - auth.multiUserBasic.persistence.enabled
+  - auth.multiUserBasic.persistence.size
+  - auth.multiUserBasic.persistence.storageClass
+  - auth.multiUserBasic.persistence.accessMode
+{{- end }}
+{{- if $legacyQdrant }}
+  - qdrant.localPersistence.enabled
+  - qdrant.localPersistence.size
+  - qdrant.localPersistence.storageClass
+  - qdrant.localPersistence.accessMode
+{{- end }}
+
+================================================================================
+{{- end }}
+
 For more information and documentation:
 - GitHub: https://github.com/cbcoutinho/nextcloud-mcp-server
 - Documentation: https://github.com/cbcoutinho/nextcloud-mcp-server#readme

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
 */}}
@@ -105,6 +127,55 @@ Create the name of the PVC to use for Qdrant local persistent storage
 {{- end }}
 {{- end }}
 
+{{/*
+Create the name of the PVC to use for /app/data storage
+*/}}
+{{- define "nextcloud-mcp-server.dataStoragePvcName" -}}
+{{- if .Values.dataStorage.existingClaim }}
+{{- .Values.dataStorage.existingClaim }}
+{{- else }}
+{{- include "nextcloud-mcp-server.fullname" . }}-data-storage
+{{- end }}
+{{- end }}
+
+{{/*
+Determine if data storage PVC should be enabled (backward compatible)
+Checks new dataStorage.enabled OR legacy persistence configs
+*/}}
+{{- define "nextcloud-mcp-server.dataStorageEnabled" -}}
+{{- if .Values.dataStorage.enabled -}}
+true
+{{- else if and (eq .Values.auth.mode "multi-user-basic") .Values.auth.multiUserBasic.enableOfflineAccess .Values.auth.multiUserBasic.persistence.enabled -}}
+true
+{{- else if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled -}}
+true
+{{- else -}}
+false
+{{- end -}}
+{{- end }}
+
+{{/*
+Check if legacy multi-user-basic persistence config is being used
+*/}}
+{{- define "nextcloud-mcp-server.legacyMultiUserBasicPersistence" -}}
+{{- if and (eq .Values.auth.mode "multi-user-basic") .Values.auth.multiUserBasic.enableOfflineAccess .Values.auth.multiUserBasic.persistence.enabled (not .Values.dataStorage.enabled) -}}
+true
+{{- else -}}
+false
+{{- end -}}
+{{- end }}
+
+{{/*
+Check if legacy qdrant persistence config is being used
+*/}}
+{{- define "nextcloud-mcp-server.legacyQdrantPersistence" -}}
+{{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled (not .Values.dataStorage.enabled) -}}
+true
+{{- else -}}
+false
+{{- end -}}
+{{- end }}
+
 {{/*
 Return the MCP server port
 */}}

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 (replaces deprecated ENABLE_OFFLINE_ACCESS)
+            - name: ENABLE_BACKGROUND_OPERATIONS
+              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 or .Values.auth.multiUserBasic.clientId .Values.auth.multiUserBasic.existingSecret }}
+            # 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
@@ -87,7 +122,7 @@ spec:
               value: {{ include "nextcloud-mcp-server.publicIssuerUrl" . | quote }}
             - name: NEXTCLOUD_OIDC_SCOPES
               value: {{ .Values.auth.oauth.scopes | quote }}
-            {{- if .Values.auth.oauth.clientId }}
+            {{- if or .Values.auth.oauth.clientId .Values.auth.oauth.existingSecret }}
             - name: NEXTCLOUD_OIDC_CLIENT_ID
               valueFrom:
                 secretKeyRef:
@@ -147,16 +182,16 @@ spec:
               value: {{ .Values.documentProcessing.custom.types | quote }}
             {{- end }}
             {{- end }}
-            # Vector Sync
-            - name: VECTOR_SYNC_ENABLED
-              value: {{ .Values.vectorSync.enabled | quote }}
-            {{- if .Values.vectorSync.enabled }}
+            # Semantic Search (replaces deprecated VECTOR_SYNC_ENABLED)
+            - name: ENABLE_SEMANTIC_SEARCH
+              value: {{ .Values.semanticSearch.enabled | quote }}
+            {{- if .Values.semanticSearch.enabled }}
             - name: VECTOR_SYNC_SCAN_INTERVAL
-              value: {{ .Values.vectorSync.scanInterval | quote }}
+              value: {{ .Values.semanticSearch.scanInterval | quote }}
             - name: VECTOR_SYNC_PROCESSOR_WORKERS
-              value: {{ .Values.vectorSync.processorWorkers | quote }}
+              value: {{ .Values.semanticSearch.processorWorkers | quote }}
             - name: VECTOR_SYNC_QUEUE_MAX_SIZE
-              value: {{ .Values.vectorSync.queueMaxSize | quote }}
+              value: {{ .Values.semanticSearch.queueMaxSize | quote }}
             {{- end }}
             # Document Chunking (always set, used by vector sync processor)
             - name: DOCUMENT_CHUNK_SIZE
@@ -251,10 +286,8 @@ spec:
             - name: oauth-storage
               mountPath: /app/.oauth
             {{- end }}
-            {{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled }}
-            - name: qdrant-data
+            - name: data-storage
               mountPath: /app/data
-            {{- end }}
             {{- with .Values.volumeMounts }}
             {{- toYaml . | nindent 12 }}
             {{- end }}
@@ -266,10 +299,12 @@ spec:
           persistentVolumeClaim:
             claimName: {{ include "nextcloud-mcp-server.oauthPvcName" . }}
         {{- end }}
-        {{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled }}
-        - name: qdrant-data
+        - name: data-storage
+        {{- if eq (include "nextcloud-mcp-server.dataStorageEnabled" .) "true" }}
           persistentVolumeClaim:
-            claimName: {{ include "nextcloud-mcp-server.qdrantPvcName" . }}
+            claimName: {{ include "nextcloud-mcp-server.dataStoragePvcName" . }}
+        {{- else }}
+          emptyDir: {}
         {{- end }}
         {{- with .Values.volumes }}
         {{- toYaml . | nindent 8 }}

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

@@ -16,20 +16,34 @@ spec:
       storage: {{ .Values.auth.oauth.persistence.size }}
 {{- end }}
 ---
-{{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled (not .Values.qdrant.localPersistence.existingClaim) }}
+{{- if and (eq (include "nextcloud-mcp-server.dataStorageEnabled" .) "true") (not .Values.dataStorage.existingClaim) }}
+{{- $legacyMultiUserBasic := eq (include "nextcloud-mcp-server.legacyMultiUserBasicPersistence" .) "true" }}
+{{- $legacyQdrant := eq (include "nextcloud-mcp-server.legacyQdrantPersistence" .) "true" }}
+{{- $accessMode := .Values.dataStorage.accessMode }}
+{{- $storageClass := .Values.dataStorage.storageClass }}
+{{- $size := .Values.dataStorage.size }}
+{{- if $legacyMultiUserBasic }}
+{{- $accessMode = .Values.auth.multiUserBasic.persistence.accessMode }}
+{{- $storageClass = .Values.auth.multiUserBasic.persistence.storageClass }}
+{{- $size = .Values.auth.multiUserBasic.persistence.size }}
+{{- else if $legacyQdrant }}
+{{- $accessMode = .Values.qdrant.localPersistence.accessMode }}
+{{- $storageClass = .Values.qdrant.localPersistence.storageClass }}
+{{- $size = .Values.qdrant.localPersistence.size }}
+{{- end }}
 apiVersion: v1
 kind: PersistentVolumeClaim
 metadata:
-  name: {{ include "nextcloud-mcp-server.fullname" . }}-qdrant-data
+  name: {{ include "nextcloud-mcp-server.fullname" . }}-data-storage
   labels:
     {{- include "nextcloud-mcp-server.labels" . | nindent 4 }}
 spec:
   accessModes:
-    - {{ .Values.qdrant.localPersistence.accessMode }}
-  {{- if .Values.qdrant.localPersistence.storageClass }}
-  storageClassName: {{ .Values.qdrant.localPersistence.storageClass }}
+    - {{ $accessMode }}
+  {{- if $storageClass }}
+  storageClassName: {{ $storageClass }}
   {{- end }}
   resources:
     requests:
-      storage: {{ .Values.qdrant.localPersistence.size }}
+      storage: {{ $size }}
 {{- end }}

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

@@ -26,21 +26,29 @@ nextcloud:
   # Example: https://mcp.example.com
   mcpServerUrl: ""
 
-  # Public issuer URL for OAuth (OAuth mode only)
-  # If not specified, defaults to nextcloud.host
-  # Only set this if your Nextcloud is accessible at a different URL for OAuth
+  # Public issuer URL for browser-accessible OAuth authorization endpoints (OAuth mode only)
+  # ONLY used to make authorization endpoints accessible to users' browsers
+  # All server-to-server communication (token endpoint, JWKS, introspection, userinfo)
+  # uses URLs from OIDC discovery without any rewriting
+  #
+  # Use case: When MCP server accesses Nextcloud at one URL but browsers need a different
+  # public URL for OAuth login (e.g., server uses internal DNS, browsers use public domain)
+  #
+  # If not specified, defaults to nextcloud.host (works when MCP server and browsers
+  # both access Nextcloud at the same URL)
   # Example: https://cloud.example.com
   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"
-  # basic: Uses username/password (recommended for most users)
+  # Authentication mode: "basic", "multi-user-basic", or "oauth"
+  # 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 +66,47 @@ 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"
@@ -90,6 +139,27 @@ auth:
       # Use existing PVC
       existingClaim: ""
 
+# Data Storage Configuration
+# Persistent volume for /app/data directory
+# Used for: token databases, qdrant persistent storage, and any app data
+# When disabled, uses emptyDir (non-persistent, but still writable)
+dataStorage:
+  # Enable persistent storage for /app/data
+  # Set to true when using:
+  # - Multi-user basic auth with offline access (stores tokens.db)
+  # - Qdrant persistent mode (stores vector database)
+  # - Any feature requiring persistent app data
+  # Set to false for basic auth without persistence (uses emptyDir)
+  enabled: false
+  # Storage class (leave empty for default)
+  storageClass: ""
+  accessMode: ReadWriteOnce
+  # Size for data storage (should accommodate tokens.db and/or qdrant data)
+  # Recommended: 1Gi minimum, 5Gi for production with qdrant
+  size: 1Gi
+  # Use existing PVC
+  existingClaim: ""
+
 # MCP server configuration
 mcp:
   # Transport mode (default: streamable-http for SSE)
@@ -316,10 +386,11 @@ extraEnvFrom: []
 # - secretRef:
 #     name: my-secret
 
-# Vector Sync Configuration
-# Background synchronization of Nextcloud content into vector database for semantic search
-vectorSync:
-  # Enable background vector synchronization
+# Semantic Search Configuration
+# Enable semantic search with BM25 hybrid search and background synchronization
+# of Nextcloud content into vector database
+semanticSearch:
+  # Enable semantic search and background vector synchronization
   enabled: false
   # Scan interval in seconds (how often to check for changes)
   scanInterval: 3600
@@ -330,7 +401,7 @@ vectorSync:
 
 # Document Chunking Configuration
 # Controls how documents are split into chunks before embedding
-# Only relevant when vectorSync.enabled is true
+# Only relevant when semanticSearch.enabled is true
 documentChunking:
   # Number of words per chunk (default: 512)
   # Smaller chunks (256-384): Better for precise searches, more chunks to store

docker-compose.yml

@@ -3,11 +3,13 @@ services:
   # https://hub.docker.com/_/mariadb
   db:
     # Note: Check the recommend version here: https://docs.nextcloud.com/server/latest/admin_manual/installation/system_requirements.html#server
-    image: docker.io/library/mariadb:lts@sha256:1cac8492bd78b1ec693238dc600be173397efd7b55eabc725abc281dc855b482
+    image: docker.io/library/mariadb:lts@sha256:8164f184d16c30e2f159e30518113667b796306dff0fe558876ab1ff521a682f
     restart: always
     command: --transaction-isolation=READ-COMMITTED
     volumes:
       - db:/var/lib/mysql
+    ports:
+      - 127.0.0.1:3306:3306
     environment:
       - MYSQL_ROOT_PASSWORD=password
       - MYSQL_PASSWORD=password
@@ -17,14 +19,14 @@ services:
   # Note: Redis is an external service. You can find more information about the configuration here:
   # https://hub.docker.com/_/redis
   redis:
-    image: docker.io/library/redis:alpine@sha256:6cbef353e480a8a6e7f10ec545f13d7d3fa85a212cdcc5ffaf5a1c818b9d3798
+    image: docker.io/library/redis:alpine@sha256:2afba59292f25f5d1af200496db41bea2c6c816b059f57ae74703a50a03a27d0
     restart: always
 
   app:
-    image: docker.io/library/nextcloud:32.0.3@sha256:53231a9fb9233af2c15bfe70fc03ebe639fd53243fa42a9369884b1e0008deae
+    image: docker.io/library/nextcloud:32.0.6@sha256:dcf9c6019d05df721bb7bada99748964c95446ea479771e9073ceaded733407e
     restart: always
     ports:
-      - 0.0.0.0:8080:80
+      - 127.0.0.1:8080:80
     depends_on:
       - redis
       - db
@@ -35,7 +37,6 @@ services:
       # 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/astrolabe:/opt/apps/astrolabe:ro
     environment:
       - NEXTCLOUD_TRUSTED_DOMAINS=app
       - NEXTCLOUD_ADMIN_USER=admin
@@ -52,14 +53,14 @@ services:
       retries: 30
 
   recipes:
-    image: docker.io/library/nginx:alpine@sha256:052b75ab72f690f33debaa51c7e08d9b969a0447a133eb2b99cc905d9188cb2b
+    image: docker.io/library/nginx:alpine@sha256:5878d06ae4c83d73285438255f705bb3f9a736f41cd24876ed25bb33faf76c7d
     restart: always
     volumes:
       - ./tests/fixtures/test_recipe.html:/usr/share/nginx/html/test_recipe.html:ro
       - ./tests/fixtures/nginx.conf:/etc/nginx/nginx.conf:ro
 
   unstructured:
-    image: downloads.unstructured.io/unstructured-io/unstructured-api:latest@sha256:54282d3a25f33fd6cf69bc45b3d37770f213593f58b6dfe5e85fe546376b2807
+    image: downloads.unstructured.io/unstructured-io/unstructured-api:latest@sha256:ba6cb073af079c498e9466a5a9152ba4b6c9cad12efeeaf053ba383023d5db08
     restart: always
     ports:
       - 127.0.0.1:8002:8000
@@ -86,8 +87,8 @@ services:
       - NEXTCLOUD_PASSWORD=admin
       - NEXTCLOUD_PUBLIC_ISSUER_URL=http://localhost:8080
 
-      # Vector sync configuration (ADR-007)
-      - VECTOR_SYNC_ENABLED=true
+      # Semantic search configuration (ADR-007, ADR-021)
+      #- ENABLE_SEMANTIC_SEARCH=true
       - VECTOR_SYNC_SCAN_INTERVAL=60
       - VECTOR_SYNC_PROCESSOR_WORKERS=1
 
@@ -135,15 +136,23 @@ services:
     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_BACKGROUND_OPERATIONS=true
 
       # Token storage (required for middleware initialization)
       - TOKEN_ENCRYPTION_KEY=ESF1BvEQdGYsCluwMx9Cxvw3uh5pFowPH7Rg_nIliyo=
       - TOKEN_STORAGE_DB=/app/data/tokens.db
 
-      # Vector sync disabled (stateless pass-through mode)
-      - VECTOR_SYNC_ENABLED=false
+      - ENABLE_SEMANTIC_SEARCH=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:
@@ -169,7 +178,7 @@ services:
       - NEXTCLOUD_OIDC_SCOPES=openid profile email 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
 
       # Refresh token storage (ADR-002 Tier 1)
-      - ENABLE_OFFLINE_ACCESS=true
+      - ENABLE_BACKGROUND_OPERATIONS=true
       - TOKEN_ENCRYPTION_KEY=ESF1BvEQdGYsCluwMx9Cxvw3uh5pFowPH7Rg_nIliyo=
       - TOKEN_STORAGE_DB=/app/data/tokens.db
 
@@ -177,8 +186,8 @@ 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
+      # Semantic search configuration (ADR-007, ADR-021)
+      - ENABLE_SEMANTIC_SEARCH=true
       - VECTOR_SYNC_SCAN_INTERVAL=60
       - VECTOR_SYNC_PROCESSOR_WORKERS=1
 
@@ -198,7 +207,7 @@ services:
       - oauth-tokens:/app/data
 
   keycloak:
-    image: quay.io/keycloak/keycloak:26.4.7@sha256:9409c59bdfb65dbffa20b11e6f18b8abb9281d480c7ca402f51ed3d5977e6007
+    image: quay.io/keycloak/keycloak:26.5.4@sha256:ae8efb0d218d8921334b03a2dbee7069a0b868240691c50a3ffc9f42fabba8b4
     command:
       - "start-dev"
       - "--import-realm"
@@ -246,7 +255,7 @@ services:
       - NEXTCLOUD_PUBLIC_ISSUER_URL=http://localhost:8888/realms/nextcloud-mcp
 
       # Refresh token storage (ADR-002 Tier 1 & 2)
-      - ENABLE_OFFLINE_ACCESS=true
+      - ENABLE_BACKGROUND_OPERATIONS=true
       - TOKEN_ENCRYPTION_KEY=ESF1BvEQdGYsCluwMx9Cxvw3uh5pFowPH7Rg_nIliyo=
       - TOKEN_STORAGE_DB=/app/data/tokens.db
 
@@ -279,13 +288,13 @@ services:
       - 127.0.0.1:8081:8081
     environment:
       - SMITHERY_DEPLOYMENT=true
-      - VECTOR_SYNC_ENABLED=false
+      - ENABLE_SEMANTIC_SEARCH=false
       - PORT=8081
     profiles:
       - smithery
 
   qdrant:
-    image: qdrant/qdrant:v1.16.2@sha256:dab6de32f7b2cc599985a7c764db3e8b062f70508fb85ca074aa856f829bf335
+    image: docker.io/qdrant/qdrant:v1.17.0@sha256:f1c7272cdac52b38c1a0e89313922d940ba50afd90d593a1605dbbc214e66ffb
     restart: always
     ports:
       - 127.0.0.1:6333:6333  # REST API

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/auth-flows.md

@@ -0,0 +1,422 @@
+# Authentication Flows by Deployment Mode
+
+This document provides a unified reference for authentication flows across all deployment modes. For configuration details, see [Authentication](authentication.md). For OAuth protocol details, see [OAuth Architecture](oauth-architecture.md).
+
+## Quick Reference Matrix
+
+| Mode | Client → MCP → NC | Background Sync | Astrolabe → MCP |
+|------|-------------------|-----------------|-----------------|
+| [Single-User BasicAuth](#1-single-user-basicauth) | Embedded credentials | Same credentials | N/A |
+| [Multi-User BasicAuth](#2-multi-user-basicauth) | Header pass-through | App password (optional) | Bearer token |
+| [OAuth Single-Audience](#3-oauth-single-audience-default) | Multi-audience token | Refresh token exchange | Bearer token |
+| [OAuth Token Exchange](#4-oauth-token-exchange-rfc-8693) | RFC 8693 exchange | Refresh token exchange | Bearer token |
+| [Smithery Stateless](#5-smithery-stateless) | Session parameters | Not supported | N/A |
+
+## Communication Patterns
+
+This document covers three distinct communication patterns:
+
+1. **MCP Client → MCP Server → Nextcloud**: Interactive tool calls initiated by users through MCP clients (Claude Desktop, etc.)
+2. **MCP Server → Nextcloud**: Background operations like vector sync that run without user interaction
+3. **Astrolabe → MCP Server**: Nextcloud app backend communication for settings UI and unified search
+
+---
+
+## Deployment Modes
+
+### 1. Single-User BasicAuth
+
+**Use Case:** Personal Nextcloud instance, local development, single-user deployments.
+
+#### MCP Client → MCP Server → Nextcloud
+
+```
+MCP Client                    MCP Server                   Nextcloud
+    │                             │                            │
+    │── MCP Request ─────────────▶│                            │
+    │   (no auth required)        │                            │
+    │                             │── HTTP + BasicAuth ───────▶│
+    │                             │   Authorization: Basic     │
+    │                             │   (embedded credentials)   │
+    │                             │◀── API Response ───────────│
+    │◀── Tool Result ─────────────│                            │
+```
+
+**Key characteristics:**
+- Credentials embedded in server configuration (`NEXTCLOUD_USERNAME`, `NEXTCLOUD_PASSWORD`)
+- Single shared `NextcloudClient` created at startup
+- No MCP-level authentication required (server trusts local clients)
+- All requests use the same Nextcloud user
+
+**Implementation:** `context.py:78-79` - Returns shared client from lifespan context
+
+#### Background Sync
+
+Uses the same embedded credentials as interactive requests. The background job accesses Nextcloud with the configured username/password.
+
+**Implementation:** Background jobs use `get_settings()` to access credentials
+
+#### Astrolabe Integration
+
+Not applicable - Astrolabe is only used in multi-user deployments where users need personal settings and token management.
+
+---
+
+### 2. Multi-User BasicAuth
+
+**Use Case:** Internal deployment where users provide their own credentials via HTTP headers.
+
+#### MCP Client → MCP Server → Nextcloud
+
+```
+MCP Client                    MCP Server                   Nextcloud
+    │                             │                            │
+    │── MCP Request ─────────────▶│                            │
+    │   Authorization: Basic      │                            │
+    │   (user credentials)        │                            │
+    │                             │── BasicAuthMiddleware ────▶│
+    │                             │   Extracts credentials     │
+    │                             │                            │
+    │                             │── HTTP + BasicAuth ───────▶│
+    │                             │   (pass-through)           │
+    │                             │◀── API Response ───────────│
+    │◀── Tool Result ─────────────│                            │
+```
+
+**Key characteristics:**
+- `BasicAuthMiddleware` extracts credentials from `Authorization: Basic` header
+- Credentials passed through to Nextcloud (not stored)
+- Client created per-request from extracted credentials
+- Stateless - no credential storage between requests
+
+**Implementation:** `context.py:187-248` - `_get_client_from_basic_auth()` extracts credentials from request state
+
+#### Background Sync (Optional)
+
+Requires `ENABLE_OFFLINE_ACCESS=true`. Users can store app passwords via Astrolabe for background operations.
+
+```
+Astrolabe                     MCP Server                   Nextcloud
+    │                             │                            │
+    │── Store App Password ──────▶│                            │
+    │   (via management API)      │                            │
+    │                             │── Store in SQLite ────────▶│
+    │                             │   (encrypted)              │
+    │◀── Confirmation ────────────│                            │
+    │                             │                            │
+    │         [Background Job]    │                            │
+    │                             │── Retrieve app password ──▶│
+    │                             │   (from encrypted storage) │
+    │                             │── HTTP + BasicAuth ───────▶│
+    │                             │   (stored app password)    │
+    │                             │◀── API Response ───────────│
+```
+
+**Requirements:**
+- `ENABLE_OFFLINE_ACCESS=true`
+- `TOKEN_ENCRYPTION_KEY` for credential encryption
+- `TOKEN_STORAGE_DB` for SQLite storage path
+
+#### Astrolabe → MCP Server
+
+```
+Astrolabe                     MCP Server                   Nextcloud OIDC
+    │                             │                            │
+    │── OAuth Flow ──────────────▶│◀── Token from IdP ────────▶│
+    │   (user initiates)          │                            │
+    │                             │                            │
+    │── Bearer Token ────────────▶│                            │
+    │   (management API calls)    │                            │
+    │                             │── Validate via JWKS ──────▶│
+    │                             │   (or introspection)       │
+    │◀── API Response ────────────│                            │
+```
+
+**Key characteristics:**
+- Astrolabe has its own OAuth client (`astrolabe_client_id` in Nextcloud config)
+- Tokens are validated by MCP server using Nextcloud OIDC JWKS
+- Authorization check: `token.sub == requested_resource_owner`
+- Any valid Nextcloud OIDC token accepted (relaxed audience validation per ADR-018)
+
+**Implementation:** `unified_verifier.py:120-183` - `verify_token_for_management_api()` validates without strict audience check
+
+---
+
+### 3. OAuth Single-Audience (Default)
+
+**Use Case:** Multi-user deployment with OAuth authentication. Tokens work for both MCP and Nextcloud.
+
+This is the default mode when `NEXTCLOUD_USERNAME`/`NEXTCLOUD_PASSWORD` are not set.
+
+#### MCP Client → MCP Server → Nextcloud
+
+```
+MCP Client                    MCP Server                   Nextcloud
+    │                             │                            │
+    │── Bearer Token ────────────▶│                            │
+    │   aud: ["mcp-server",       │                            │
+    │         "nextcloud"]        │                            │
+    │                             │── Validate MCP audience ──▶│
+    │                             │   (UnifiedTokenVerifier)   │
+    │                             │                            │
+    │                             │── HTTP + Same Token ──────▶│
+    │                             │   Authorization: Bearer    │
+    │                             │   (multi-audience token)   │
+    │                             │                            │
+    │                             │   NC validates its own aud │
+    │                             │◀── API Response ───────────│
+    │◀── Tool Result ─────────────│                            │
+```
+
+**Key characteristics:**
+- Token contains both audiences: `aud: ["mcp-server", "nextcloud"]`
+- MCP server validates only MCP audience (per RFC 7519)
+- Nextcloud independently validates its own audience
+- No token exchange needed - same token used throughout
+- Stateless operation for interactive requests
+
+**Token validation flow:**
+1. `UnifiedTokenVerifier.verify_token()` validates MCP audience
+2. Token passed directly to Nextcloud via `get_client_from_context()`
+3. Nextcloud validates its own audience when receiving API calls
+
+**Implementation:**
+- `unified_verifier.py:185-252` - `_verify_mcp_audience()` validates MCP audience only
+- `context.py:96-99` - Uses token directly in multi-audience mode
+
+#### Background Sync
+
+Requires `ENABLE_OFFLINE_ACCESS=true`. Uses stored refresh tokens to obtain access tokens for background operations.
+
+```
+                              MCP Server                   Nextcloud OIDC
+                                  │                            │
+    [Background Job starts]       │                            │
+                                  │── Get refresh token ──────▶│
+                                  │   (from encrypted storage) │
+                                  │                            │
+                                  │── Token refresh request ──▶│
+                                  │   grant_type=refresh_token │
+                                  │   scope=openid profile ... │
+                                  │◀── New access + refresh ───│
+                                  │   (rotation)               │
+                                  │                            │
+                                  │── Store rotated refresh ──▶│
+                                  │   (encrypted)              │
+                                  │                            │
+                                  │── HTTP + Access Token ────▶│
+                                  │   Authorization: Bearer    │
+                                  │◀── API Response ───────────│
+```
+
+**Key characteristics:**
+- Refresh tokens stored encrypted in SQLite (`TOKEN_STORAGE_DB`)
+- Nextcloud OIDC rotates refresh tokens on every use (one-time use)
+- `TokenBrokerService` handles token lifecycle
+- Per-user locking prevents race conditions during concurrent refresh
+
+**Implementation:**
+- `token_broker.py:269-362` - `get_background_token()` handles refresh with locking
+- `token_broker.py:428-509` - `_refresh_access_token_with_scopes()` exchanges refresh token
+
+#### Astrolabe → MCP Server
+
+Same as Multi-User BasicAuth. See [Astrolabe → MCP Server](#astrolabe--mcp-server) above.
+
+---
+
+### 4. OAuth Token Exchange (RFC 8693)
+
+**Use Case:** Multi-user deployment where MCP tokens are separate from Nextcloud tokens. Provides stronger security boundaries.
+
+Enabled by `ENABLE_TOKEN_EXCHANGE=true`.
+
+#### MCP Client → MCP Server → Nextcloud
+
+```
+MCP Client                    MCP Server                   Nextcloud OIDC
+    │                             │                            │
+    │── Bearer Token ────────────▶│                            │
+    │   aud: "mcp-server"         │                            │
+    │   (MCP audience only)       │                            │
+    │                             │── Validate MCP audience ──▶│
+    │                             │                            │
+    │                             │── RFC 8693 Exchange ──────▶│
+    │                             │   grant_type=              │
+    │                             │     urn:ietf:params:oauth: │
+    │                             │     grant-type:token-exchange
+    │                             │   subject_token=<mcp-token>│
+    │                             │   requested_audience=      │
+    │                             │     "nextcloud"            │
+    │                             │◀── Delegated Token ────────│
+    │                             │   aud: "nextcloud"         │
+    │                             │                            │
+    │                             │── HTTP + Delegated Token ─▶│
+    │                             │   Authorization: Bearer    │
+    │                             │◀── API Response ───────────│
+    │◀── Tool Result ─────────────│                            │
+```
+
+**Key characteristics:**
+- Strict audience separation: MCP token has `aud: "mcp-server"` only
+- Server exchanges for Nextcloud-audience token on each request
+- Ephemeral delegated tokens (not cached by default)
+- Strongest security boundary between MCP and Nextcloud access
+
+**Token exchange details:**
+- Uses RFC 8693 "urn:ietf:params:oauth:grant-type:token-exchange"
+- Subject token: MCP access token
+- Requested audience: Nextcloud resource URI
+- Result: Short-lived token scoped for Nextcloud
+
+**Implementation:**
+- `token_broker.py:220-267` - `get_session_token()` performs on-demand exchange
+- `token_exchange.py` - `exchange_token_for_delegation()` implements RFC 8693
+- `context.py:88-94` - Routes to session client in exchange mode
+
+#### Background Sync
+
+Same as OAuth Single-Audience. Uses stored refresh tokens from Flow 2 provisioning.
+
+```
+                              MCP Server                   Nextcloud OIDC
+                                  │                            │
+    [User provisions access]      │                            │
+                                  │── Flow 2 OAuth ───────────▶│
+                                  │   client_id="mcp-server"   │
+                                  │   scope=offline_access ... │
+                                  │◀── Refresh Token ──────────│
+                                  │   (stored encrypted)       │
+                                  │                            │
+    [Background Job runs later]   │                            │
+                                  │── Refresh for background ─▶│
+                                  │   (same as single-audience)│
+```
+
+**Key difference from interactive:**
+- Interactive: On-demand token exchange per request
+- Background: Uses pre-provisioned refresh tokens (Flow 2)
+
+#### Astrolabe → MCP Server
+
+Same as Multi-User BasicAuth. See [Astrolabe → MCP Server](#astrolabe--mcp-server) above.
+
+---
+
+### 5. Smithery Stateless
+
+**Use Case:** Multi-tenant SaaS deployment via Smithery platform. Fully stateless.
+
+Enabled by `SMITHERY_DEPLOYMENT=true`.
+
+#### MCP Client → MCP Server → Nextcloud
+
+```
+MCP Client                    MCP Server                   Nextcloud
+    │                             │                            │
+    │── SSE Connect ─────────────▶│                            │
+    │   ?nextcloud_url=...        │                            │
+    │   &username=...             │                            │
+    │   &app_password=...         │                            │
+    │                             │── SmitheryConfigMiddleware │
+    │                             │   Extract URL params       │
+    │                             │                            │
+    │── MCP Request ─────────────▶│                            │
+    │   (no Authorization header) │                            │
+    │                             │── Create per-request ─────▶│
+    │                             │   NextcloudClient          │
+    │                             │                            │
+    │                             │── HTTP + BasicAuth ───────▶│
+    │                             │   (from session params)    │
+    │                             │◀── API Response ───────────│
+    │◀── Tool Result ─────────────│                            │
+```
+
+**Key characteristics:**
+- Configuration passed via URL query parameters (Smithery `configSchema`)
+- No persistent state - client created fresh per request
+- No OAuth infrastructure
+- No background sync support (stateless)
+- No admin UI available
+
+**Required session parameters:**
+- `nextcloud_url`: Nextcloud instance URL
+- `username`: Nextcloud username
+- `app_password`: Nextcloud app password
+
+**Implementation:** `context.py:108-184` - `_get_client_from_session_config()` creates client from session params
+
+#### Background Sync
+
+Not supported. Smithery mode is fully stateless with no credential storage.
+
+#### Astrolabe Integration
+
+Not applicable. Smithery deployments don't integrate with Astrolabe.
+
+---
+
+## Configuration Quick Reference
+
+### Single-User BasicAuth
+```bash
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+```
+
+### Multi-User BasicAuth
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+ENABLE_MULTI_USER_BASIC_AUTH=true
+
+# Optional: For background sync
+ENABLE_OFFLINE_ACCESS=true
+TOKEN_ENCRYPTION_KEY=<32-byte-key>
+TOKEN_STORAGE_DB=/data/tokens.db
+```
+
+### OAuth Single-Audience (Default)
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+# No username/password triggers OAuth mode
+
+# Optional: Static client credentials (instead of DCR)
+NEXTCLOUD_OIDC_CLIENT_ID=<client-id>
+NEXTCLOUD_OIDC_CLIENT_SECRET=<client-secret>
+
+# Optional: For background sync
+ENABLE_OFFLINE_ACCESS=true
+TOKEN_ENCRYPTION_KEY=<32-byte-key>
+TOKEN_STORAGE_DB=/data/tokens.db
+```
+
+### OAuth Token Exchange
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+ENABLE_TOKEN_EXCHANGE=true
+NEXTCLOUD_OIDC_CLIENT_ID=<client-id>
+NEXTCLOUD_OIDC_CLIENT_SECRET=<client-secret>
+
+# Optional: For background sync
+ENABLE_OFFLINE_ACCESS=true
+TOKEN_ENCRYPTION_KEY=<32-byte-key>
+TOKEN_STORAGE_DB=/data/tokens.db
+```
+
+### Smithery Stateless
+```bash
+SMITHERY_DEPLOYMENT=true
+# All other config comes from session URL parameters
+```
+
+---
+
+## Related Documentation
+
+- [Authentication](authentication.md) - Configuration details and setup guides
+- [OAuth Architecture](oauth-architecture.md) - Deep OAuth protocol details
+- [ADR-004: Progressive Consent](ADR-004-mcp-application-oauth.md) - Dual OAuth flow architecture
+- [ADR-005: Token Audience Validation](ADR-005-token-audience-validation.md) - Audience validation strategy
+- [ADR-018: Nextcloud PHP App](ADR-018-nextcloud-php-app-for-settings-ui.md) - Astrolabe integration
+- [ADR-020: Deployment Modes](ADR-020-deployment-modes-and-configuration-validation.md) - Mode detection and validation

docs/authentication.md

@@ -140,6 +140,97 @@ Basic Authentication uses username and password credentials directly.
 - [Configuration](configuration.md#basic-authentication-legacy) - BasicAuth environment variables
 - [Running the Server](running.md#basicauth-mode-legacy) - BasicAuth examples
 
+## Hybrid Authentication (Multi-User BasicAuth + OAuth)
+
+When running in multi-user BasicAuth mode with `ENABLE_OFFLINE_ACCESS=true`, the server operates in **hybrid authentication mode**. This provides the simplicity of BasicAuth for normal operations with the security of OAuth for administrative functions.
+
+### Authentication Domains
+
+**MCP Operations** (Tools, Resources):
+- **Auth Method**: BasicAuth (HTTP Basic username/password)
+- **Characteristics**:
+  - Stateless - no token storage
+  - Simple configuration
+  - Direct credential validation against Nextcloud
+  - Credentials passed per-request in Authorization header
+- **Used For**: MCP tool calls from Claude, MCP client operations
+
+**Management APIs** (Webhooks, Admin UI):
+- **Auth Method**: OAuth bearer tokens
+- **Characteristics**:
+  - Per-user authorization via OAuth consent flow
+  - Refresh tokens stored for background operations
+  - Token validation via UnifiedTokenVerifier
+  - Explicit user consent required
+- **Used For**: Astrolabe admin UI, webhook management, vector sync operations
+
+### Configuration
+
+```env
+# Enable multi-user BasicAuth
+ENABLE_MULTI_USER_BASIC_AUTH=true
+
+# Enable hybrid mode (OAuth provisioning for management APIs)
+ENABLE_OFFLINE_ACCESS=true
+
+# Enable background sync (required for hybrid mode currently)
+VECTOR_SYNC_ENABLED=true
+
+# Encryption key for refresh token storage
+TOKEN_ENCRYPTION_KEY=<base64-encoded-key>
+
+# Nextcloud connection
+NEXTCLOUD_HOST=https://cloud.example.com
+
+# OAuth credentials (optional - uses DCR if not set)
+NEXTCLOUD_OIDC_CLIENT_ID=<client-id>
+NEXTCLOUD_OIDC_CLIENT_SECRET=<client-secret>
+```
+
+### OAuth Provisioning Flow
+
+1. Admin opens Astrolabe admin settings in Nextcloud
+2. Clicks "Authorize" to enable webhook management
+3. Redirected to `/oauth/authorize-nextcloud` on MCP server
+4. MCP server redirects to Nextcloud OAuth consent page
+5. Admin grants OAuth consent (scopes: `openid`, `profile`, `offline_access`)
+6. Redirected back to `/oauth/callback` on MCP server
+7. MCP server stores refresh token (encrypted)
+8. Admin can now manage webhooks from Astrolabe UI
+
+### Benefits
+
+- **Simple MCP client setup**: Use BasicAuth (no OAuth complexity for end users)
+- **Secure background operations**: Webhooks use per-user OAuth tokens (no shared credentials)
+- **Explicit authorization**: Admins must explicitly grant OAuth consent for webhook operations
+- **Per-user isolation**: Each admin's webhook operations use their own refresh token
+
+### Trade-offs
+
+- **Two auth systems**: More complex server configuration than pure BasicAuth or OAuth
+- **OAuth setup required**: Admins must complete OAuth flow before managing webhooks
+- **Token storage**: Requires database and encryption key for refresh tokens
+
+### Comparison
+
+| Feature | Pure BasicAuth | Hybrid Mode | Pure OAuth |
+|---------|---------------|-------------|------------|
+| MCP Operations | BasicAuth | BasicAuth | OAuth Bearer Token |
+| Management API | N/A | OAuth Bearer Token | OAuth Bearer Token |
+| Webhook Operations | N/A | OAuth Refresh Token | OAuth Refresh Token |
+| MCP Client Setup | Simple | Simple | Complex (PKCE flow) |
+| Admin UI Auth | N/A | OAuth Consent | OAuth Login |
+| Token Storage | None | Refresh tokens only | All tokens |
+| Deployment Complexity | Low | Medium | High |
+
+### Astrolabe User Setup (Hybrid Mode)
+
+For Astrolabe-specific user setup instructions in hybrid mode, see the [Astrolabe documentation](https://github.com/cbcoutinho/astrolabe/blob/master/docs/user-setup-hybrid-mode.md).
+
+### See Also
+- [OAuth Architecture](oauth-architecture.md) - Progressive Consent (Flow 2) details
+- [Configuration](configuration.md#enable_offline_access) - Hybrid mode configuration
+
 ## Mode Detection
 
 The server automatically detects the authentication mode:

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)
-- [Basic Authentication Configuration](#basic-authentication-legacy)
+- [Single-User BasicAuth](#single-user-basicauth-mode) - Simplest for personal instances
+- [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
@@ -108,10 +171,104 @@ NEXTCLOUD_PASSWORD=your_app_password_or_password
 
 ---
 
+## SSL/TLS Configuration (Optional)
+
+If your Nextcloud instance uses a self-signed certificate or a private CA (common with reverse proxies like Traefik or Caddy), the MCP server will reject the connection by default. Use these settings to configure certificate verification.
+
+### Custom CA Bundle (Recommended)
+
+Point the server at your CA certificate file:
+
+```dotenv
+NEXTCLOUD_CA_BUNDLE=/etc/ssl/certs/my-ca.pem
+```
+
+With Docker, mount the certificate as a read-only volume:
+
+```bash
+docker run \
+  -v /path/to/my-ca.pem:/etc/ssl/certs/my-ca.pem:ro \
+  -e NEXTCLOUD_CA_BUNDLE=/etc/ssl/certs/my-ca.pem \
+  -e NEXTCLOUD_HOST=https://nextcloud.local \
+  --env-file .env \
+  ghcr.io/cbcoutinho/nextcloud-mcp-server:latest
+```
+
+### Disable Verification (Development Only)
+
+> [!WARNING]
+> Disabling TLS verification is insecure. Only use this for local development or testing.
+
+```dotenv
+NEXTCLOUD_VERIFY_SSL=false
+```
+
+### Environment Variables Reference
+
+| Variable | Required | Default | Description |
+|----------|----------|---------|-------------|
+| `NEXTCLOUD_VERIFY_SSL` | ⚠️ Optional | `true` | Set to `false` to disable TLS certificate verification |
+| `NEXTCLOUD_CA_BUNDLE` | ⚠️ Optional | - | Path to a PEM CA bundle file for custom certificate authorities |
+
+### Scope
+
+These settings apply to **all** outbound connections to Nextcloud and its OIDC endpoints, including:
+
+- Nextcloud API calls (Notes, Calendar, Contacts, WebDAV, etc.)
+- OIDC discovery and token endpoints
+- OAuth client registration (DCR)
+- Health checks
+
+They do **not** affect connections to internal services (Ollama, Qdrant, Unstructured) which have their own SSL configuration.
+
+---
+
 ## 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 +283,7 @@ 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 +302,7 @@ 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 +323,7 @@ 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 +440,15 @@ 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)
-VECTOR_SYNC_ENABLED=true              # Enable background indexing
+# Semantic search (ADR-007, ADR-021)
+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 +458,8 @@ 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 +530,11 @@ 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 |
-| `VECTOR_SYNC_ENABLED` | ⚠️ Optional | `false` | Enable background vector indexing |
+| `QDRANT_COLLECTION` | ⚠️ Optional | Auto-generated | Qdrant collection name |
 | `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 +544,9 @@ 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 +556,7 @@ services:
   mcp:
     environment:
       - QDRANT_URL=http://qdrant:6333
-      - VECTOR_SYNC_ENABLED=true
+      - ENABLE_SEMANTIC_SEARCH=true
 
   qdrant:
     image: qdrant/qdrant:latest
@@ -545,6 +709,7 @@ 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 +718,4 @@ 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/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"

docs/webhook-management-guide.md

@@ -0,0 +1,339 @@
+# Webhook Management Guide
+
+This guide explains how to enable and disable webhooks for vector sync in each MCP server deployment mode. Webhooks enable near-real-time synchronization of content changes to the vector database, complementing the default polling-based sync.
+
+**Related ADRs:**
+- ADR-010: Webhook-Based Vector Sync
+- ADR-020: Deployment Modes and Configuration Validation
+
+## Prerequisites
+
+Before enabling webhooks, ensure:
+
+1. **Nextcloud 30+** with `webhook_listeners` app enabled
+2. **[Astrolabe app](https://github.com/cbcoutinho/astrolabe)** installed in Nextcloud (provides settings UI and credentials API)
+3. **MCP server** accessible from Nextcloud via HTTP(S)
+4. **Vector sync enabled** on the MCP server
+
+## Webhook Architecture Overview
+
+The webhook system has two components:
+
+1. **Webhook Registration** - Configuring Nextcloud to send change notifications to the MCP server
+2. **Background Sync Credentials** - Allowing the MCP server to access Nextcloud APIs on behalf of users
+
+Both must be configured for webhooks to function properly.
+
+## Deployment Mode Specifics
+
+### 1. Single-User BasicAuth
+
+**Configuration:**
+```bash
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+VECTOR_SYNC_ENABLED=true
+```
+
+**Enable Webhooks:**
+1. Register webhooks using occ commands (requires Nextcloud admin):
+   ```bash
+   # Enable webhook_listeners app
+   php occ app:enable webhook_listeners
+
+   # Register webhooks for vector sync
+   php occ webhook_listeners:add \
+     --event "OCP\Files\Events\Node\NodeCreatedEvent" \
+     --uri "http://mcp-server:8000/webhooks/nextcloud" \
+     --method POST
+
+   # Repeat for other events (see Event Types below)
+   ```
+
+2. Optionally reduce polling frequency:
+   ```bash
+   VECTOR_SYNC_SCAN_INTERVAL=86400  # 24 hours
+   ```
+
+**Disable Webhooks:**
+```bash
+# List registered webhooks
+php occ webhook_listeners:list
+
+# Remove specific webhook by ID
+php occ webhook_listeners:remove <webhook-id>
+```
+
+**Notes:**
+- Simplest mode - admin credentials used for all operations
+- No per-user provisioning required
+- Background sync runs as the configured admin user
+
+---
+
+### 2. Multi-User BasicAuth Pass-Through
+
+**Configuration:**
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+ENABLE_MULTI_USER_BASIC_AUTH=true
+ENABLE_BACKGROUND_OPERATIONS=true
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/app/data/tokens.db
+VECTOR_SYNC_ENABLED=true
+# OAuth client for Astrolabe API access
+NEXTCLOUD_OIDC_CLIENT_ID=<client-id>
+NEXTCLOUD_OIDC_CLIENT_SECRET=<client-secret>
+```
+
+**Credential Architecture:**
+This mode uses **two separate credential mechanisms**:
+
+1. **OAuth Session** (for management API access, including webhooks):
+   - Obtained via browser OAuth flow (`/oauth/login`)
+   - Stores refresh token in MCP server's `tokens.db`
+   - Used for webhook registration/management APIs
+
+2. **App Password** (for background sync):
+   - Generated in Nextcloud Security settings
+   - Stored encrypted in Nextcloud's `oc_preferences` via Astrolabe
+   - Used by background scanners to access Nextcloud APIs
+
+**Enable Webhooks:**
+
+#### Step 1: Complete OAuth Login (for Management API)
+Users must authorize the MCP server to access their Nextcloud:
+
+1. Navigate to **Nextcloud Settings → Astrolabe** (Personal settings)
+2. Click **"Authorize via OAuth"** under "Option 1"
+3. Complete OAuth consent flow
+4. Verify the page shows "Background Sync Access: Active"
+
+#### Step 2: Configure App Password (for Background Sync)
+Since OAuth refresh tokens have short expiry, users should also configure an app password:
+
+1. Navigate to **Nextcloud Settings → Security**
+2. Generate a new app password (name it "Astrolabe" or "MCP Server")
+3. Return to **Nextcloud Settings → Astrolabe**
+4. Under "Option 2: App Password", paste the app password
+5. Click **Save**
+
+#### Step 3: Register Webhooks (Admin)
+Same as Single-User BasicAuth:
+```bash
+php occ webhook_listeners:add \
+  --event "OCP\Files\Events\Node\NodeCreatedEvent" \
+  --uri "http://mcp-server:8003/webhooks/nextcloud" \
+  --method POST
+```
+
+**Disable Webhooks:**
+
+*Per-User:*
+1. Navigate to **Nextcloud Settings → Astrolabe**
+2. Click **"Revoke Access"** (for OAuth tokens) or **"Revoke Access"** (for app password)
+
+*System-Wide:*
+```bash
+php occ webhook_listeners:remove <webhook-id>
+```
+
+**Troubleshooting:**
+
+If OAuth login fails with "Access forbidden - Your client is not authorized":
+1. Check if OAuth client is registered:
+   ```sql
+   SELECT id, name, client_identifier FROM oc_oidc_clients
+   WHERE dcr = 1 ORDER BY id DESC LIMIT 5;
+   ```
+2. Restart MCP server to trigger DCR re-registration
+3. Verify `NEXTCLOUD_OIDC_CLIENT_ID` and `NEXTCLOUD_OIDC_CLIENT_SECRET` are set
+
+If background sync fails with "User no longer provisioned":
+1. Verify app password is stored:
+   ```sql
+   SELECT userid, configkey FROM oc_preferences
+   WHERE appid = 'astrolabe' AND userid = 'username';
+   ```
+2. Ensure user completed **both** OAuth login AND app password setup
+
+---
+
+### 3. OAuth Single-Audience (Default OAuth Mode)
+
+**Configuration:**
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+# No NEXTCLOUD_USERNAME/PASSWORD
+ENABLE_BACKGROUND_OPERATIONS=true
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/app/data/tokens.db
+VECTOR_SYNC_ENABLED=true
+```
+
+**Enable Webhooks:**
+
+#### Step 1: User Provisioning
+Users authorize via OAuth with `offline_access` scope:
+
+1. MCP client initiates OAuth flow
+2. User consents to requested scopes including `offline_access`
+3. MCP server stores refresh token for background operations
+
+Alternatively, via Astrolabe UI:
+1. Navigate to **Nextcloud Settings → Astrolabe**
+2. Click **"Authorize via OAuth"**
+3. Complete consent flow
+
+#### Step 2: Register Webhooks (Admin)
+```bash
+php occ webhook_listeners:add \
+  --event "OCP\Files\Events\Node\NodeCreatedEvent" \
+  --uri "http://mcp-server:8001/webhooks/nextcloud" \
+  --method POST
+```
+
+**Disable Webhooks:**
+
+*Per-User:*
+- Via Astrolabe UI: Click "Disable Indexing" or "Disconnect"
+- Via MCP tool: Use `revoke_nextcloud_access` if available
+
+*System-Wide:*
+```bash
+php occ webhook_listeners:remove <webhook-id>
+```
+
+---
+
+### 4. OAuth Token Exchange (RFC 8693)
+
+**Configuration:**
+```bash
+NEXTCLOUD_HOST=http://nextcloud.example.com
+ENABLE_TOKEN_EXCHANGE=true
+ENABLE_BACKGROUND_OPERATIONS=true
+TOKEN_ENCRYPTION_KEY=<key>
+TOKEN_STORAGE_DB=/app/data/tokens.db
+VECTOR_SYNC_ENABLED=true
+```
+
+**Enable/Disable Webhooks:**
+Same process as OAuth Single-Audience. The token exchange happens transparently when the MCP server accesses Nextcloud APIs.
+
+---
+
+### 5. Smithery Stateless
+
+**Configuration:**
+- Configuration from session URL params
+- `VECTOR_SYNC_ENABLED=false` (required)
+
+**Webhooks:**
+**Not supported.** This mode is stateless with no persistent storage or background operations.
+
+---
+
+## Webhook Event Types
+
+Register these webhook events for full vector sync coverage:
+
+### File/Note Events
+```bash
+# Use BeforeNodeDeletedEvent for deletions (includes node.id)
+php occ webhook_listeners:add --event "OCP\Files\Events\Node\NodeCreatedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+php occ webhook_listeners:add --event "OCP\Files\Events\Node\NodeWrittenEvent" --uri "$MCP_URL/webhooks/nextcloud"
+php occ webhook_listeners:add --event "OCP\Files\Events\Node\BeforeNodeDeletedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+```
+
+### Calendar Events
+```bash
+php occ webhook_listeners:add --event "OCP\Calendar\Events\CalendarObjectCreatedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+php occ webhook_listeners:add --event "OCP\Calendar\Events\CalendarObjectUpdatedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+php occ webhook_listeners:add --event "OCP\Calendar\Events\CalendarObjectDeletedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+```
+
+### Tables Events
+```bash
+php occ webhook_listeners:add --event "OCA\Tables\Event\RowAddedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+php occ webhook_listeners:add --event "OCA\Tables\Event\RowUpdatedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+php occ webhook_listeners:add --event "OCA\Tables\Event\RowDeletedEvent" --uri "$MCP_URL/webhooks/nextcloud"
+```
+
+## Security Considerations
+
+### Webhook Authentication
+Configure `WEBHOOK_SECRET` to require authentication for incoming webhooks:
+
+```bash
+# MCP Server
+WEBHOOK_SECRET=<generate-random-secret>
+
+# Nextcloud webhook registration
+php occ webhook_listeners:add \
+  --event "..." \
+  --uri "$MCP_URL/webhooks/nextcloud" \
+  --header "Authorization: Bearer <secret>"
+```
+
+### Token Storage
+- Refresh tokens and app passwords are encrypted using `TOKEN_ENCRYPTION_KEY`
+- Store the key securely (environment variable, secrets manager)
+- Different users have isolated credential storage
+
+## Monitoring
+
+### MCP Server Logs
+```bash
+# Docker
+docker compose logs mcp-multi-user-basic | grep -i webhook
+
+# Key log messages
+# - "Queued document from webhook: ..." - Success
+# - "Webhook authentication failed" - Auth error
+# - "User X no longer provisioned" - Missing credentials
+```
+
+### Nextcloud Logs
+```bash
+docker compose exec app cat /var/www/html/data/nextcloud.log | \
+  jq 'select(.message | contains("webhook"))' | tail
+```
+
+### Database Checks
+```sql
+-- Check registered webhooks
+SELECT * FROM oc_webhook_listeners;
+
+-- Check OAuth clients
+SELECT id, name, token_type FROM oc_oidc_clients WHERE dcr = 1;
+
+-- Check user credentials stored by Astrolabe app
+SELECT userid, configkey FROM oc_preferences WHERE appid = 'astrolabe';
+```
+
+## Common Issues
+
+### "Access forbidden - Your client is not authorized to connect"
+**Cause:** OAuth client registration expired or not present in Nextcloud
+**Fix:** Restart MCP server to trigger DCR re-registration
+
+### "User X no longer provisioned, stopping scanner"
+**Cause:** Background sync credentials missing or expired
+**Fix:** User must complete credential provisioning (see mode-specific steps)
+
+### "Failed to fetch" in browser console during OAuth
+**Cause:** Network issue between browser and MCP server callback endpoint
+**Fix:** Verify MCP server is accessible at the configured `NEXTCLOUD_MCP_SERVER_URL`
+
+### Webhooks not firing
+**Causes:**
+1. `webhook_listeners` app not enabled
+2. Webhook not registered for the event type
+3. Background job workers not running
+**Fix:**
+```bash
+php occ app:enable webhook_listeners
+php occ background:cron  # or configure systemd cron
+```

env.sample

@@ -1,203 +1,249 @@
-# 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:
-
-# Option 1: OAuth2/OIDC (RECOMMENDED - More Secure)
-# - Requires Nextcloud OIDC app installed and configured
-# - Admin must enable "Dynamic Client Registration" in OIDC app settings
-# - Leave NEXTCLOUD_USERNAME and NEXTCLOUD_PASSWORD empty to use OAuth mode
-# - 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
+# ============================================
+# SINGLE-USER BASICAUTH MODE
+# ============================================
+# Simplest deployment - one user, credentials in environment
+# Use for: Personal instances, local development, testing
+#
+# Required:
 NEXTCLOUD_USERNAME=
 NEXTCLOUD_PASSWORD=
+#
+# Optional features (semantic search, document processing):
+# See "Optional Features" section below
 
+# ============================================
+# MULTI-USER BASICAUTH MODE
+# ============================================
+# Users provide credentials in request headers (pass-through)
+# Use for: Multi-user without OAuth, simple shared deployments
+#
+# Required:
+#ENABLE_MULTI_USER_BASIC_AUTH=true
+#
+# 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
+
+# ============================================
+# OAUTH SINGLE-AUDIENCE MODE (Recommended)
+# ============================================
+# Multi-user OAuth with single-audience tokens
+# Use for: Multi-user production deployments, enhanced security
+# Tokens work for both MCP server and Nextcloud APIs (pass-through)
+#
+# Required: None (uses Dynamic Client Registration if credentials not provided)
+#
+# Optional - Pre-registered OAuth Client:
+# If you pre-register the client instead of using DCR:
+#NEXTCLOUD_OIDC_CLIENT_ID=
+#NEXTCLOUD_OIDC_CLIENT_SECRET=
+#
+# Optional - Background Operations (for semantic search, future features):
+# Enable refresh token storage for offline access
+# 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:
+# Auto-detected from NEXTCLOUD_HOST if not set
+#NEXTCLOUD_OIDC_DISCOVERY_URL=
+#
+# Optional - Custom Scopes:
+# Default: openid profile email offline_access notes:* calendar:* contacts:* tables:* webdav:* deck:* cookbook:*
+#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
+
+# ============================================
+# OAUTH TOKEN EXCHANGE MODE (Advanced)
+# ============================================
+# Multi-user OAuth with RFC 8693 token exchange
+# Use for: Advanced deployments requiring separate MCP and Nextcloud tokens
+# MCP tokens are separate from Nextcloud tokens
+#
+# Required:
+#ENABLE_TOKEN_EXCHANGE=true
+#
+# Optional - Pre-registered OAuth Client:
+# 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
+
+# ============================================
+# SMITHERY STATELESS MODE
+# ============================================
+# Stateless multi-tenant deployment for Smithery platform
+# Configuration comes from session URL parameters
+# No persistent storage, no OAuth, no vector sync
+#
+# Required: None (all config from session URL)
+# This mode is activated automatically when deployed to Smithery
+
+# ============================================
+# OPTIONAL FEATURES (All Deployment Modes)
+# ============================================
+
+# ===== SEMANTIC SEARCH =====
+# 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)
+#VECTOR_SYNC_SCAN_INTERVAL=300
+#
+# Concurrent indexing workers (default: 3)
+#VECTOR_SYNC_PROCESSOR_WORKERS=3
+#
+# Max queued documents (default: 10000)
+#VECTOR_SYNC_QUEUE_MAX_SIZE=10000
+
+# ===== DOCUMENT PROCESSING =====
+# Extract text from PDFs, images, DOCX, etc. for semantic search
+# Disabled by default
+#
+#ENABLE_DOCUMENT_PROCESSING=false
+#DOCUMENT_PROCESSOR=unstructured
+#
+# 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
+
+# ===== SSL/TLS =====
+# For Nextcloud behind reverse proxies with self-signed or private CA certificates
+#
+# Disable TLS certificate verification (insecure, development only):
+#NEXTCLOUD_VERIFY_SSL=false
+#
+# Use a custom CA bundle (path to PEM file):
+#NEXTCLOUD_CA_BUNDLE=/etc/ssl/certs/my-ca.pem
+#
+# Docker example: mount the CA bundle as a volume
+#   docker run -v /path/to/ca.pem:/etc/ssl/certs/my-ca.pem:ro \
+#     -e NEXTCLOUD_CA_BUNDLE=/etc/ssl/certs/my-ca.pem ...
+
+# ===== SECURITY & ADVANCED =====
 # Cookie security (browser UI)
 # Auto-detects from NEXTCLOUD_HOST protocol if not set
-# Set explicitly for non-standard setups
 #COOKIE_SECURE=true
 
 # ============================================
-# Document Processing Configuration
+# DEPRECATED VARIABLES (Backward Compatibility)
 # ============================================
-# Enable document processing (PDF, DOCX, images, etc.)
-# Set to false to disable all document processing
-ENABLE_DOCUMENT_PROCESSING=false
-
-# Default processor to use when multiple are available
-# Options: unstructured, tesseract, custom
-DOCUMENT_PROCESSOR=unstructured
-
-# ============================================
-# Unstructured.io Processor
-# ============================================
-# Enable Unstructured processor (requires unstructured service in docker-compose)
-# This is a cloud-based/API processor supporting many document types
-ENABLE_UNSTRUCTURED=false
-
-# Unstructured API endpoint
-UNSTRUCTURED_API_URL=http://unstructured:8000
-
-# Request timeout in seconds (default: 120)
-# OCR operations can take 30-120 seconds for large documents
-UNSTRUCTURED_TIMEOUT=120
-
-# Parsing strategy: auto, fast, hi_res
-# - auto: Automatically choose based on document type
-# - fast: Fast parsing without OCR
-# - hi_res: High-resolution with OCR (slowest, most accurate)
-UNSTRUCTURED_STRATEGY=auto
-
-# OCR languages (comma-separated ISO 639-3 codes)
-# Common: eng=English, deu=German, fra=French, spa=Spanish
-UNSTRUCTURED_LANGUAGES=eng,deu
-
-# Progress reporting interval in seconds (default: 10)
-# During long-running OCR operations, progress notifications are sent to the MCP client
-# at this interval to prevent timeouts and provide status updates
-PROGRESS_INTERVAL=10
-
-# ============================================
-# Tesseract Processor (Local OCR)
-# ============================================
-# Enable Tesseract processor (requires tesseract binary installed)
-# This is a local, lightweight OCR solution for images only
-ENABLE_TESSERACT=false
-
-# Path to tesseract executable (optional, auto-detected if in PATH)
-#TESSERACT_CMD=/usr/bin/tesseract
-
-# OCR language (e.g., eng, deu, eng+deu for multiple)
-TESSERACT_LANG=eng
-
-# ============================================
-# Custom Processor (Your own API)
-# ============================================
-# Enable custom document processor via HTTP API
-ENABLE_CUSTOM_PROCESSOR=false
-
-# Unique name for your processor
-#CUSTOM_PROCESSOR_NAME=my_ocr
-
-# 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
-# ============================================
-# EXPERIMENTAL: Semantic search for Notes app (multi-app support planned)
-# Requires: Qdrant vector database + Ollama embedding service
-# Disabled by default
-
-# Enable background vector indexing
-VECTOR_SYNC_ENABLED=false
-
-# 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
-
-# ============================================
-# Qdrant Vector Database Configuration
-# ============================================
-# Choose ONE of three modes:
-# 1. In-memory mode (default): Set neither QDRANT_URL nor QDRANT_LOCATION
-# 2. Persistent local: Set QDRANT_LOCATION=/path/to/data
-# 3. Network mode: Set QDRANT_URL=http://qdrant:6333
-
-# Network mode: URL to Qdrant service
-#QDRANT_URL=http://qdrant:6333
-
-# Local mode: Path to store vectors (use :memory: for in-memory)
-#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
-# ============================================
-# Ollama endpoint for embeddings (if not set, uses SimpleEmbeddingProvider fallback)
-#OLLAMA_BASE_URL=http://ollama:11434
-
-# Embedding model to use (default: nomic-embed-text, 768 dimensions)
-# Changing this creates a new collection (requires re-embedding all documents)
-#OLLAMA_EMBEDDING_MODEL=nomic-embed-text
-
-# Verify SSL certificates (default: true)
-#OLLAMA_VERIFY_SSL=true
-
-# ============================================
-# 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
+# These variables still work but will be removed in v1.0.0
+# Please migrate to new names:
+#
+# Old Name                  → New Name
+# VECTOR_SYNC_ENABLED      → ENABLE_SEMANTIC_SEARCH
+# ENABLE_OFFLINE_ACCESS    → ENABLE_BACKGROUND_OPERATIONS
+#
+# Migration is optional - both old and new names work
+# Deprecation warnings will be logged when old names are used

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/versions/20260113_1200_002_add_app_passwords.py

@@ -0,0 +1,50 @@
+"""Add app_passwords table for multi-user BasicAuth mode
+
+This migration adds support for storing app passwords that are provisioned
+via Astrolabe's personal settings. This enables background sync in
+multi-user BasicAuth mode without requiring OAuth.
+
+Revision ID: 002
+Revises: 001
+Create Date: 2026-01-13 12:00:00.000000
+
+"""
+
+from alembic import op
+
+# revision identifiers, used by Alembic.
+revision = "002"
+down_revision = "001"
+branch_labels = None
+depends_on = None
+
+
+def upgrade() -> None:
+    """Add app_passwords table for multi-user BasicAuth mode."""
+
+    # App passwords table for multi-user BasicAuth background sync
+    op.execute(
+        """
+        CREATE TABLE IF NOT EXISTS app_passwords (
+            user_id TEXT PRIMARY KEY,
+            encrypted_password BLOB NOT NULL,
+            created_at INTEGER NOT NULL,
+            updated_at INTEGER NOT NULL
+        )
+        """
+    )
+
+    # Index for efficient user lookups
+    op.execute(
+        """
+        CREATE INDEX IF NOT EXISTS idx_app_passwords_updated
+        ON app_passwords(updated_at)
+        """
+    )
+
+
+def downgrade() -> None:
+    """Drop app_passwords table."""
+
+    op.execute("DROP INDEX IF EXISTS idx_app_passwords_updated")
+    op.execute("DROP TABLE IF EXISTS app_passwords")

nextcloud_mcp_server/api/__init__.py

@@ -3,4 +3,74 @@
 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.
+
+This package is organized into modules by domain:
+- management.py: Server status, user sessions, shared helpers
+- passwords.py: App password provisioning for multi-user BasicAuth
+- webhooks.py: Webhook registration management
+- visualization.py: Search and PDF visualization endpoints
 """
+
+# Re-export all public functions for backward compatibility
+from nextcloud_mcp_server.api.management import (
+    __version__,
+    _parse_float_param,
+    _parse_int_param,
+    _sanitize_error_for_client,
+    _validate_query_string,
+    extract_bearer_token,
+    get_server_status,
+    get_user_session,
+    get_vector_sync_status,
+    revoke_user_access,
+    validate_token_and_get_user,
+)
+from nextcloud_mcp_server.api.passwords import (
+    delete_app_password,
+    get_app_password_status,
+    provision_app_password,
+)
+from nextcloud_mcp_server.api.visualization import (
+    get_chunk_context,
+    get_pdf_preview,
+    unified_search,
+    vector_search,
+)
+from nextcloud_mcp_server.api.webhooks import (
+    create_webhook,
+    delete_webhook,
+    get_installed_apps,
+    list_webhooks,
+)
+
+__all__ = [
+    # Version
+    "__version__",
+    # Shared helpers (from management.py)
+    "extract_bearer_token",
+    "validate_token_and_get_user",
+    "_sanitize_error_for_client",
+    "_parse_int_param",
+    "_parse_float_param",
+    "_validate_query_string",
+    # Status endpoints (from management.py)
+    "get_server_status",
+    "get_vector_sync_status",
+    # Session endpoints (from management.py)
+    "get_user_session",
+    "revoke_user_access",
+    # Password endpoints (from passwords.py)
+    "provision_app_password",
+    "get_app_password_status",
+    "delete_app_password",
+    # Webhook endpoints (from webhooks.py)
+    "get_installed_apps",
+    "list_webhooks",
+    "create_webhook",
+    "delete_webhook",
+    # Visualization endpoints (from visualization.py)
+    "unified_search",
+    "vector_search",
+    "get_chunk_context",
+    "get_pdf_preview",
+]

nextcloud_mcp_server/api/passwords.py

@@ -0,0 +1,427 @@
+"""App password management API endpoints.
+
+Provides REST API endpoints for app password provisioning in multi-user BasicAuth mode.
+These endpoints are used by the Nextcloud PHP app (Astrolabe) to:
+- Store app passwords for background sync operations
+- Check app password status
+- Delete stored app passwords
+
+Authentication is via BasicAuth with the user's Nextcloud credentials.
+Passwords are validated against Nextcloud before being stored.
+"""
+
+import base64
+import logging
+import re
+import time
+from collections import defaultdict
+
+import httpx
+from starlette.requests import Request
+from starlette.responses import JSONResponse
+
+from nextcloud_mcp_server.api.management import _sanitize_error_for_client
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+from nextcloud_mcp_server.config import get_settings
+
+from ..http import nextcloud_httpx_client
+
+logger = logging.getLogger(__name__)
+
+# App password format regex (Nextcloud format: xxxxx-xxxxx-xxxxx-xxxxx-xxxxx)
+APP_PASSWORD_PATTERN = re.compile(
+    r"^[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}-[a-zA-Z0-9]{5}$"
+)
+
+# Timeout for Nextcloud API validation requests (seconds)
+NEXTCLOUD_VALIDATION_TIMEOUT = 10.0
+
+# Rate limiting configuration for app password provisioning
+# Limits: 5 attempts per user per hour
+RATE_LIMIT_MAX_ATTEMPTS = 5
+RATE_LIMIT_WINDOW_SECONDS = 3600  # 1 hour
+
+# In-memory rate limiter storage
+# Structure: {user_id: [(timestamp, success), ...]}
+_rate_limit_attempts: dict[str, list[tuple[float, bool]]] = defaultdict(list)
+
+
+def _check_rate_limit(user_id: str) -> tuple[bool, int]:
+    """Check if user is rate limited for app password operations.
+
+    Implements a sliding window rate limiter to prevent brute-force attacks
+    on the app password provisioning endpoint.
+
+    Args:
+        user_id: User identifier to check
+
+    Returns:
+        Tuple of (is_allowed, seconds_until_retry)
+        - is_allowed: True if request should be allowed
+        - seconds_until_retry: Seconds to wait if rate limited (0 if allowed)
+    """
+    current_time = time.time()
+    window_start = current_time - RATE_LIMIT_WINDOW_SECONDS
+
+    # Clean up old attempts outside the window
+    _rate_limit_attempts[user_id] = [
+        (ts, success)
+        for ts, success in _rate_limit_attempts[user_id]
+        if ts > window_start
+    ]
+
+    # Count recent attempts (both successful and failed)
+    recent_attempts = len(_rate_limit_attempts[user_id])
+
+    if recent_attempts >= RATE_LIMIT_MAX_ATTEMPTS:
+        # Find when the oldest attempt in the window will expire
+        oldest_attempt = min(ts for ts, _ in _rate_limit_attempts[user_id])
+        seconds_until_retry = int(
+            oldest_attempt + RATE_LIMIT_WINDOW_SECONDS - current_time
+        )
+        return False, max(1, seconds_until_retry)
+
+    return True, 0
+
+
+def _record_rate_limit_attempt(user_id: str, success: bool) -> None:
+    """Record an app password provisioning attempt for rate limiting.
+
+    Args:
+        user_id: User identifier
+        success: Whether the attempt was successful
+    """
+    _rate_limit_attempts[user_id].append((time.time(), success))
+
+
+def _extract_basic_auth(
+    request: Request, path_user_id: str
+) -> tuple[str, str, JSONResponse | None]:
+    """Extract and validate BasicAuth credentials from request.
+
+    Validates:
+    1. Authorization header is present and valid BasicAuth format
+    2. Username in credentials matches the path user_id
+
+    Args:
+        request: Starlette request with Authorization header
+        path_user_id: User ID from the URL path to verify against
+
+    Returns:
+        Tuple of (username, password, error_response)
+        - If successful: (username, password, None)
+        - If failed: ("", "", JSONResponse with error)
+    """
+    auth_header = request.headers.get("Authorization")
+
+    if not auth_header or not auth_header.startswith("Basic "):
+        return (
+            "",
+            "",
+            JSONResponse(
+                {"success": False, "error": "Missing BasicAuth credentials"},
+                status_code=401,
+            ),
+        )
+
+    try:
+        # Decode BasicAuth
+        encoded = auth_header.split(" ", 1)[1]
+        decoded = base64.b64decode(encoded).decode("utf-8")
+        username, password = decoded.split(":", 1)
+    except Exception:
+        return (
+            "",
+            "",
+            JSONResponse(
+                {"success": False, "error": "Invalid BasicAuth format"},
+                status_code=401,
+            ),
+        )
+
+    # Verify username matches path user_id
+    if username != path_user_id:
+        logger.warning(
+            f"Username mismatch in app password operation for path user {path_user_id}"
+        )
+        return (
+            "",
+            "",
+            JSONResponse(
+                {"success": False, "error": "Username does not match path user_id"},
+                status_code=403,
+            ),
+        )
+
+    return username, password, None
+
+
+async def _get_app_password_storage(request: Request) -> RefreshTokenStorage:
+    """Get or initialize RefreshTokenStorage for app password operations.
+
+    Checks app.state.storage first, then falls back to creating from environment.
+    This helper avoids repeated storage initialization logic across endpoints.
+
+    Args:
+        request: Starlette request with app state
+
+    Returns:
+        Initialized RefreshTokenStorage instance
+    """
+    storage = getattr(request.app.state, "storage", None)
+
+    if not storage:
+        # Multi-user BasicAuth mode may not have oauth_context
+        # Initialize storage from environment
+        storage = RefreshTokenStorage.from_env()
+        await storage.initialize()
+
+    return storage
+
+
+async def provision_app_password(request: Request) -> JSONResponse:
+    """POST /api/v1/users/{user_id}/app-password - Store app password for background sync.
+
+    This endpoint is used by Astrolabe (Nextcloud PHP app) to provision app passwords
+    for multi-user BasicAuth mode background sync.
+
+    The request must include BasicAuth credentials where:
+    - username: Nextcloud user ID (must match path user_id)
+    - password: The app password being provisioned
+
+    The MCP server validates the app password against Nextcloud before storing it.
+    This proves the user owns the password and has access to Nextcloud.
+
+    Security model:
+    - User identity is verified via BasicAuth against Nextcloud
+    - App password is encrypted before storage
+    - Only the user who owns the password can provision it
+    - Rate limited to prevent brute-force attacks
+    """
+    # Get user_id from path
+    path_user_id = request.path_params.get("user_id")
+    if not path_user_id:
+        return JSONResponse(
+            {"success": False, "error": "Missing user_id in path"},
+            status_code=400,
+        )
+
+    # Check rate limit before processing
+    is_allowed, retry_after = _check_rate_limit(path_user_id)
+    if not is_allowed:
+        logger.warning(
+            f"Rate limit exceeded for app password provisioning: {path_user_id}"
+        )
+        return JSONResponse(
+            {
+                "success": False,
+                "error": f"Rate limit exceeded. Try again in {retry_after} seconds.",
+            },
+            status_code=429,
+            headers={"Retry-After": str(retry_after)},
+        )
+
+    # Extract and validate BasicAuth credentials
+    username, app_password, error_response = _extract_basic_auth(request, path_user_id)
+    if error_response is not None:
+        _record_rate_limit_attempt(path_user_id, success=False)
+        return error_response
+
+    # Validate app password format
+    if not APP_PASSWORD_PATTERN.match(app_password):
+        _record_rate_limit_attempt(path_user_id, success=False)
+        return JSONResponse(
+            {"success": False, "error": "Invalid app password format"},
+            status_code=400,
+        )
+
+    # Get Nextcloud host from settings
+    settings = get_settings()
+    nextcloud_host = settings.nextcloud_host
+
+    if not nextcloud_host:
+        logger.error("NEXTCLOUD_HOST not configured")
+        return JSONResponse(
+            {"success": False, "error": "Server not configured"},
+            status_code=500,
+        )
+
+    # Validate app password against Nextcloud
+    try:
+        async with nextcloud_httpx_client(
+            timeout=NEXTCLOUD_VALIDATION_TIMEOUT
+        ) as client:
+            # Use OCS API to verify credentials
+            test_url = f"{nextcloud_host}/ocs/v1.php/cloud/user"
+            response = await client.get(
+                test_url,
+                auth=(username, app_password),
+                params={"format": "json"},
+                headers={"OCS-APIRequest": "true"},
+            )
+
+            if response.status_code != 200:
+                logger.warning(
+                    f"App password validation failed for user: HTTP {response.status_code}"
+                )
+                _record_rate_limit_attempt(path_user_id, success=False)
+                return JSONResponse(
+                    {"success": False, "error": "Invalid app password"},
+                    status_code=401,
+                )
+
+            # Verify the user ID from response matches
+            data = response.json()
+            ocs_user_id = data.get("ocs", {}).get("data", {}).get("id")
+            if ocs_user_id != username:
+                logger.warning("User ID mismatch in OCS response")
+                _record_rate_limit_attempt(path_user_id, success=False)
+                return JSONResponse(
+                    {"success": False, "error": "User ID mismatch"},
+                    status_code=403,
+                )
+
+    except httpx.RequestError as e:
+        logger.error(f"Failed to validate app password: {e}")
+        return JSONResponse(
+            {"success": False, "error": "Failed to validate credentials"},
+            status_code=500,
+        )
+
+    # Store the validated app password
+    try:
+        storage = await _get_app_password_storage(request)
+        await storage.store_app_password(username, app_password)
+
+        _record_rate_limit_attempt(path_user_id, success=True)
+        logger.info(f"Provisioned app password for user: {username}")
+
+        return JSONResponse(
+            {
+                "success": True,
+                "message": f"App password stored for {username}",
+            }
+        )
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "provision_app_password")
+        return JSONResponse(
+            {"success": False, "error": error_msg},
+            status_code=500,
+        )
+
+
+async def get_app_password_status(request: Request) -> JSONResponse:
+    """GET /api/v1/users/{user_id}/app-password - Check if user has provisioned app password.
+
+    Returns status of background sync access for multi-user BasicAuth mode.
+
+    Requires BasicAuth with the user's app password for authentication.
+    """
+    # Get user_id from path
+    path_user_id = request.path_params.get("user_id")
+    if not path_user_id:
+        return JSONResponse(
+            {"success": False, "error": "Missing user_id in path"},
+            status_code=400,
+        )
+
+    # Extract and validate BasicAuth credentials
+    username, _, error_response = _extract_basic_auth(request, path_user_id)
+    if error_response is not None:
+        return error_response
+
+    try:
+        storage = await _get_app_password_storage(request)
+        app_password = await storage.get_app_password(username)
+
+        return JSONResponse(
+            {
+                "success": True,
+                "user_id": username,
+                "has_app_password": app_password is not None,
+            }
+        )
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "get_app_password_status")
+        return JSONResponse(
+            {"success": False, "error": error_msg},
+            status_code=500,
+        )
+
+
+async def delete_app_password(request: Request) -> JSONResponse:
+    """DELETE /api/v1/users/{user_id}/app-password - Delete stored app password.
+
+    Removes the user's app password from MCP server storage.
+
+    Requires BasicAuth with the user's credentials.
+    """
+    # Get user_id from path
+    path_user_id = request.path_params.get("user_id")
+    if not path_user_id:
+        return JSONResponse(
+            {"success": False, "error": "Missing user_id in path"},
+            status_code=400,
+        )
+
+    # Extract and validate BasicAuth credentials
+    username, password, error_response = _extract_basic_auth(request, path_user_id)
+    if error_response is not None:
+        return error_response
+
+    # Validate credentials against Nextcloud
+    settings = get_settings()
+    nextcloud_host = settings.nextcloud_host
+
+    try:
+        async with nextcloud_httpx_client(
+            timeout=NEXTCLOUD_VALIDATION_TIMEOUT
+        ) as client:
+            test_url = f"{nextcloud_host}/ocs/v1.php/cloud/user"
+            response = await client.get(
+                test_url,
+                auth=(username, password),
+                params={"format": "json"},
+                headers={"OCS-APIRequest": "true"},
+            )
+
+            if response.status_code != 200:
+                return JSONResponse(
+                    {"success": False, "error": "Invalid credentials"},
+                    status_code=401,
+                )
+    except httpx.RequestError as e:
+        logger.error(f"Failed to validate credentials: {e}")
+        return JSONResponse(
+            {"success": False, "error": "Failed to validate credentials"},
+            status_code=500,
+        )
+
+    try:
+        storage = await _get_app_password_storage(request)
+        deleted = await storage.delete_app_password(username)
+
+        if deleted:
+            logger.info(f"Deleted app password for user: {username}")
+            return JSONResponse(
+                {
+                    "success": True,
+                    "message": f"App password deleted for {username}",
+                }
+            )
+        else:
+            return JSONResponse(
+                {
+                    "success": True,
+                    "message": "No app password found to delete",
+                }
+            )
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "delete_app_password")
+        return JSONResponse(
+            {"success": False, "error": error_msg},
+            status_code=500,
+        )

nextcloud_mcp_server/api/visualization.py

@@ -0,0 +1,776 @@
+"""Visualization API endpoints for search and PDF preview.
+
+ADR-018: Provides REST API endpoints for the Nextcloud PHP app (Astrolabe) to:
+- Execute unified search with semantic/BM25/hybrid algorithms
+- Execute vector search with PCA visualization coordinates
+- Fetch chunk context with surrounding text
+- Render PDF pages server-side (avoiding CSP/worker issues)
+
+All endpoints require OAuth bearer token authentication via UnifiedTokenVerifier.
+"""
+
+import base64
+import logging
+from typing import Any
+
+import pymupdf
+from qdrant_client.models import FieldCondition, Filter, MatchValue
+from starlette.requests import Request
+from starlette.responses import JSONResponse
+
+from nextcloud_mcp_server.api.management import (
+    _parse_float_param,
+    _parse_int_param,
+    _sanitize_error_for_client,
+    _validate_query_string,
+    extract_bearer_token,
+    validate_token_and_get_user,
+)
+from nextcloud_mcp_server.client import NextcloudClient
+from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.embedding.service import get_embedding_service
+from nextcloud_mcp_server.search import (
+    BM25HybridSearchAlgorithm,
+    SemanticSearchAlgorithm,
+)
+from nextcloud_mcp_server.search.context import get_chunk_with_context
+from nextcloud_mcp_server.vector.placeholder import get_placeholder_filter
+from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
+from nextcloud_mcp_server.vector.visualization import compute_pca_coordinates
+
+logger = logging.getLogger(__name__)
+
+
+async def unified_search(request: Request) -> JSONResponse:
+    """POST /api/v1/search - Search endpoint for Nextcloud Unified Search.
+
+    Optimized search endpoint for the Nextcloud Unified Search provider
+    and other PHP app integrations. Returns results with metadata needed
+    for navigation to source documents.
+
+    Request body:
+    {
+        "query": "search query",
+        "algorithm": "semantic|bm25|hybrid",  // default: hybrid
+        "limit": 20,  // max: 100
+        "offset": 0,  // pagination offset
+        "include_pca": false,  // optional PCA coordinates
+        "include_chunks": true  // include text snippets
+    }
+
+    Response:
+    {
+        "results": [{
+            "id": "doc123",
+            "doc_type": "note",
+            "title": "Document Title",
+            "excerpt": "Matching text snippet...",
+            "score": 0.85,
+            "path": "/path/to/file.txt",  // for files
+            "board_id": 1,  // for deck cards
+            "card_id": 42
+        }],
+        "total_found": 150,
+        "algorithm_used": "hybrid"
+    }
+
+    Requires OAuth bearer token for user filtering.
+    """
+    settings = get_settings()
+    if not settings.vector_sync_enabled:
+        return JSONResponse(
+            {"error": "Vector sync is disabled on this server"},
+            status_code=404,
+        )
+
+    # Validate OAuth token and extract user
+    try:
+        user_id, _validated = await validate_token_and_get_user(request)
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/search: {e}")
+        return JSONResponse(
+            {
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "unified_search"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Parse request body
+        body = await request.json()
+
+        # Validate and parse parameters
+        try:
+            query = body.get("query", "")
+            _validate_query_string(query, max_length=10000)
+
+            limit = _parse_int_param(
+                str(body.get("limit")) if body.get("limit") is not None else None,
+                20,
+                1,
+                100,
+                "limit",
+            )
+
+            offset = _parse_int_param(
+                str(body.get("offset")) if body.get("offset") is not None else None,
+                0,
+                0,
+                1000000,
+                "offset",
+            )
+
+            score_threshold = _parse_float_param(
+                body.get("score_threshold"),
+                0.0,
+                0.0,
+                1.0,
+                "score_threshold",
+            )
+        except ValueError as e:
+            return JSONResponse({"error": str(e)}, status_code=400)
+
+        algorithm = body.get("algorithm", "hybrid")
+        fusion = body.get("fusion", "rrf")
+        include_pca = body.get("include_pca", False)
+        include_chunks = body.get("include_chunks", True)
+        doc_types = body.get("doc_types")  # Optional filter
+
+        if not query:
+            return JSONResponse({"results": [], "total_found": 0})
+
+        # Validate algorithm
+        valid_algorithms = {"semantic", "bm25", "hybrid"}
+        if algorithm not in valid_algorithms:
+            algorithm = "hybrid"
+
+        # Validate fusion method
+        valid_fusions = {"rrf", "dbsf"}
+        if fusion not in valid_fusions:
+            fusion = "rrf"
+
+        # Select search algorithm
+        if algorithm == "semantic":
+            search_algo = SemanticSearchAlgorithm(score_threshold=score_threshold)
+        else:
+            search_algo = BM25HybridSearchAlgorithm(
+                score_threshold=score_threshold, fusion=fusion
+            )
+
+        # Request extra results to handle offset
+        search_limit = limit + offset
+
+        # Execute search
+        all_results = []
+        if doc_types and isinstance(doc_types, list):
+            for doc_type in doc_types:
+                if doc_type:
+                    results = await search_algo.search(
+                        query=query,
+                        user_id=user_id,
+                        limit=search_limit,
+                        doc_type=doc_type,
+                    )
+                    all_results.extend(results)
+            all_results.sort(key=lambda r: r.score, reverse=True)
+        else:
+            all_results = await search_algo.search(
+                query=query,
+                user_id=user_id,
+                limit=search_limit,
+            )
+
+        # Sort results by score (no deduplication - show all chunks)
+        sorted_results = sorted(all_results, key=lambda r: r.score, reverse=True)
+
+        # Calculate total and apply pagination
+        total_found = len(sorted_results)
+        paginated_results = sorted_results[offset : offset + limit]
+
+        # Format results for Unified Search
+        formatted_results = []
+        for result in paginated_results:
+            # Get document ID (prefer note_id for notes)
+            doc_id = result.id
+            if result.metadata and "note_id" in result.metadata:
+                doc_id = result.metadata["note_id"]
+
+            result_data: dict[str, Any] = {
+                "id": doc_id,
+                "doc_type": result.doc_type,
+                "title": result.title,
+                "score": result.score,
+            }
+
+            # Include excerpt/chunk if requested (full content, no truncation)
+            if include_chunks and result.excerpt:
+                result_data["excerpt"] = result.excerpt
+
+            # Include navigation metadata from result.metadata
+            if result.metadata:
+                # File path and mimetype for files
+                if "path" in result.metadata:
+                    result_data["path"] = result.metadata["path"]
+                if "mime_type" in result.metadata:
+                    result_data["mime_type"] = result.metadata["mime_type"]
+
+                # Deck card navigation
+                if "board_id" in result.metadata:
+                    result_data["board_id"] = result.metadata["board_id"]
+                if "card_id" in result.metadata:
+                    result_data["card_id"] = result.metadata["card_id"]
+
+                # Calendar event metadata
+                if "calendar_id" in result.metadata:
+                    result_data["calendar_id"] = result.metadata["calendar_id"]
+                if "event_uid" in result.metadata:
+                    result_data["event_uid"] = result.metadata["event_uid"]
+
+            # Add PDF page metadata
+            if result.page_number is not None:
+                result_data["page_number"] = result.page_number
+            if result.page_count is not None:
+                result_data["page_count"] = result.page_count
+
+            # Add chunk metadata (always present, defaults to 0 and 1)
+            result_data["chunk_index"] = result.chunk_index
+            result_data["total_chunks"] = result.total_chunks
+
+            # Add chunk offsets for modal navigation
+            if result.chunk_start_offset is not None:
+                result_data["chunk_start_offset"] = result.chunk_start_offset
+            if result.chunk_end_offset is not None:
+                result_data["chunk_end_offset"] = result.chunk_end_offset
+
+            formatted_results.append(result_data)
+
+        response_data: dict[str, Any] = {
+            "results": formatted_results,
+            "total_found": total_found,
+            "algorithm_used": algorithm,
+        }
+
+        # Optional PCA coordinates
+        if include_pca and len(paginated_results) >= 2:
+            try:
+                if search_algo.query_embedding is not None:
+                    query_embedding = search_algo.query_embedding
+                else:
+                    embedding_service = get_embedding_service()
+                    query_embedding = await embedding_service.embed(query)
+
+                pca_data = await compute_pca_coordinates(
+                    paginated_results, query_embedding
+                )
+                response_data["pca_data"] = pca_data
+            except Exception as e:
+                logger.warning(f"Failed to compute PCA for unified search: {e}")
+
+        return JSONResponse(response_data)
+
+    except Exception as e:
+        logger.error(f"Error in unified search: {e}")
+        return JSONResponse(
+            {
+                "error": "Internal error",
+                "message": _sanitize_error_for_client(e, "unified_search"),
+            },
+            status_code=500,
+        )
+
+
+async def vector_search(request: Request) -> JSONResponse:
+    """POST /api/v1/vector-viz/search - Vector search for visualization.
+
+    Executes semantic search and returns results with optional PCA coordinates
+    for 2D visualization.
+
+    Request body:
+    {
+        "query": "search query",
+        "algorithm": "semantic|bm25|hybrid",  // default: hybrid
+        "limit": 10,  // max: 50
+        "include_pca": true,  // whether to include 2D coordinates
+        "doc_types": ["note", "file"]  // optional filter by document types
+    }
+
+    Requires OAuth bearer token for user filtering.
+    """
+    settings = get_settings()
+    if not settings.vector_sync_enabled:
+        return JSONResponse(
+            {"error": "Vector sync is disabled on this server"},
+            status_code=404,
+        )
+
+    # Validate OAuth token and extract user
+    try:
+        user_id, _validated = await validate_token_and_get_user(request)
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/vector-viz/search: {e}")
+        return JSONResponse(
+            {
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "vector_search"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Parse request body
+        body = await request.json()
+        query = body.get("query", "")
+        algorithm = body.get("algorithm", "hybrid")
+        fusion = body.get("fusion", "rrf")
+        score_threshold = body.get("score_threshold", 0.0)
+        limit = min(body.get("limit", 10), 50)  # Enforce max limit
+        include_pca = body.get("include_pca", True)
+        doc_types = body.get("doc_types")  # Optional list of document types
+
+        if not query:
+            return JSONResponse(
+                {"error": "Missing required parameter: query"},
+                status_code=400,
+            )
+
+        # Validate algorithm
+        valid_algorithms = {"semantic", "bm25", "hybrid"}
+        if algorithm not in valid_algorithms:
+            algorithm = "hybrid"
+
+        # Validate fusion method
+        valid_fusions = {"rrf", "dbsf"}
+        if fusion not in valid_fusions:
+            fusion = "rrf"
+
+        # Select search algorithm
+        if algorithm == "semantic":
+            search_algo = SemanticSearchAlgorithm(score_threshold=score_threshold)
+        else:
+            # Both "hybrid" and "bm25" use the BM25HybridSearchAlgorithm
+            # which combines dense semantic and sparse BM25 vectors
+            search_algo = BM25HybridSearchAlgorithm(
+                score_threshold=score_threshold, fusion=fusion
+            )
+
+        # Execute search for each doc_type if specified, otherwise search all
+        all_results = []
+        if doc_types and isinstance(doc_types, list):
+            # Search each doc_type separately and merge results
+            for doc_type in doc_types:
+                if doc_type:  # Skip empty strings
+                    results = await search_algo.search(
+                        query=query,
+                        user_id=user_id,
+                        limit=limit,
+                        doc_type=doc_type,
+                    )
+                    all_results.extend(results)
+            # Sort merged results by score and limit
+            all_results.sort(key=lambda r: r.score, reverse=True)
+            all_results = all_results[:limit]
+        else:
+            # Search all document types
+            all_results = await search_algo.search(
+                query=query,
+                user_id=user_id,
+                limit=limit,
+            )
+
+        # Format results for PHP client
+        formatted_results = []
+        for result in all_results:
+            formatted_result = {
+                "id": result.id,
+                "doc_type": result.doc_type,
+                "title": result.title,
+                "excerpt": result.excerpt[:200] if result.excerpt else "",
+                "score": result.score,
+                "metadata": result.metadata,
+                # Chunk information for context display
+                "chunk_index": result.chunk_index,
+                "total_chunks": result.total_chunks,
+            }
+            # Include optional fields if present
+            if result.chunk_start_offset is not None:
+                formatted_result["chunk_start_offset"] = result.chunk_start_offset
+            if result.chunk_end_offset is not None:
+                formatted_result["chunk_end_offset"] = result.chunk_end_offset
+            if result.page_number is not None:
+                formatted_result["page_number"] = result.page_number
+            if result.page_count is not None:
+                formatted_result["page_count"] = result.page_count
+            formatted_results.append(formatted_result)
+
+        response_data: dict[str, Any] = {
+            "results": formatted_results,
+            "algorithm_used": algorithm,
+            "total_documents": len(formatted_results),
+        }
+
+        # Compute PCA coordinates for visualization using shared function
+        if include_pca and len(all_results) >= 2:
+            try:
+                # Get query embedding from search algorithm or generate it
+                if search_algo.query_embedding is not None:
+                    query_embedding = search_algo.query_embedding
+                else:
+                    embedding_service = get_embedding_service()
+                    query_embedding = await embedding_service.embed(query)
+
+                pca_data = await compute_pca_coordinates(all_results, query_embedding)
+                response_data["coordinates_3d"] = pca_data["coordinates_3d"]
+                response_data["query_coords"] = pca_data["query_coords"]
+                if "pca_variance" in pca_data:
+                    response_data["pca_variance"] = pca_data["pca_variance"]
+            except Exception as e:
+                logger.warning(f"Failed to compute PCA coordinates: {e}")
+                response_data["coordinates_3d"] = []
+                response_data["query_coords"] = []
+        elif include_pca:
+            # Not enough results for PCA
+            response_data["coordinates_3d"] = []
+            response_data["query_coords"] = []
+
+        return JSONResponse(response_data)
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "vector_search")
+        return JSONResponse(
+            {"error": error_msg},
+            status_code=500,
+        )
+
+
+async def get_chunk_context(request: Request) -> JSONResponse:
+    """GET /api/v1/chunk-context - Fetch chunk text with context.
+
+    Retrieves the matched chunk along with surrounding text and metadata.
+    Used by clients to display chunk context and highlighted PDFs.
+
+    Query parameters:
+        doc_type: Document type (e.g., "note")
+        doc_id: Document ID
+        start: Chunk start offset (character position)
+        end: Chunk end offset (character position)
+        context: Characters of context before/after (default: 500)
+
+    Requires OAuth bearer token for authentication.
+    """
+    try:
+        # Validate OAuth token and extract user
+        user_id, validated = await validate_token_and_get_user(request)
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/chunk-context: {e}")
+        return JSONResponse(
+            {
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "get_chunk_context"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Get query parameters
+        doc_type = request.query_params.get("doc_type")
+        doc_id = request.query_params.get("doc_id")
+        start_str = request.query_params.get("start")
+        end_str = request.query_params.get("end")
+
+        # Validate required parameters
+        if not all([doc_type, doc_id, start_str, end_str]):
+            return JSONResponse(
+                {
+                    "success": False,
+                    "error": "Missing required parameters: doc_type, doc_id, start, end",
+                },
+                status_code=400,
+            )
+
+        # Type narrowing: we already checked these are not None above
+        assert start_str is not None
+        assert end_str is not None
+        assert doc_id is not None
+        assert doc_type is not None
+
+        # Parse and validate integer parameters with bounds checking
+        try:
+            context_chars = _parse_int_param(
+                request.query_params.get("context"),
+                500,
+                0,
+                10000,
+                "context_chars",
+            )
+            start = _parse_int_param(start_str, 0, 0, 10000000, "start")
+            end = _parse_int_param(end_str, 0, 0, 10000000, "end")
+            if end <= start:
+                raise ValueError("end must be greater than start")
+        except ValueError as e:
+            return JSONResponse({"success": False, "error": str(e)}, status_code=400)
+        # Convert doc_id to int if possible (most IDs are int)
+        doc_id_val: str | int = int(doc_id) if doc_id.isdigit() else doc_id
+
+        # Get bearer token for client initialization
+        token = extract_bearer_token(request)
+        if not token:
+            raise ValueError("Missing token")
+
+        # Get Nextcloud host from OAuth context
+        oauth_ctx = request.app.state.oauth_context
+        nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+        if not nextcloud_host:
+            raise ValueError("Nextcloud host not configured")
+
+        # Initialize authenticated Nextcloud client
+        async with NextcloudClient.from_token(
+            base_url=nextcloud_host, token=token, username=user_id
+        ) as nc_client:
+            chunk_context = await get_chunk_with_context(
+                nc_client=nc_client,
+                user_id=user_id,
+                doc_id=doc_id_val,
+                doc_type=doc_type,
+                chunk_start=start,
+                chunk_end=end,
+                context_chars=context_chars,
+            )
+
+        if chunk_context is None:
+            return JSONResponse(
+                {
+                    "success": False,
+                    "error": f"Failed to fetch chunk context for {doc_type} {doc_id}",
+                },
+                status_code=404,
+            )
+
+        # For PDF files, also fetch the highlighted page image from Qdrant if available
+        # This is useful for clients that want to show a pre-rendered image
+        highlighted_page_image = None
+        page_number = chunk_context.page_number
+
+        if doc_type == "file":
+            try:
+                settings = get_settings()
+                qdrant_client = await get_qdrant_client()
+
+                # Query for this specific chunk's highlighted image
+                points_response = await qdrant_client.scroll(
+                    collection_name=settings.get_collection_name(),
+                    scroll_filter=Filter(
+                        must=[
+                            get_placeholder_filter(),
+                            FieldCondition(
+                                key="doc_id", match=MatchValue(value=doc_id_val)
+                            ),
+                            FieldCondition(
+                                key="user_id", match=MatchValue(value=user_id)
+                            ),
+                            FieldCondition(
+                                key="chunk_start_offset", match=MatchValue(value=start)
+                            ),
+                            FieldCondition(
+                                key="chunk_end_offset", match=MatchValue(value=end)
+                            ),
+                        ]
+                    ),
+                    limit=1,
+                    with_vectors=False,
+                    with_payload=["highlighted_page_image", "page_number"],
+                )
+
+                if points_response[0]:
+                    payload = points_response[0][0].payload
+                    if payload:
+                        highlighted_page_image = payload.get("highlighted_page_image")
+                        # Trust Qdrant page number if available (might be more accurate than context expansion logic)
+                        if payload.get("page_number") is not None:
+                            page_number = payload.get("page_number")
+
+            except Exception as e:
+                logger.warning(f"Failed to fetch highlighted image: {e}")
+
+        # Build response
+        response_data = {
+            "success": True,
+            "chunk_text": chunk_context.chunk_text,
+            "before_context": chunk_context.before_context,
+            "after_context": chunk_context.after_context,
+            "has_more_before": chunk_context.has_before_truncation,
+            "has_more_after": chunk_context.has_after_truncation,
+            "page_number": page_number,
+            "chunk_index": chunk_context.chunk_index,
+            "total_chunks": chunk_context.total_chunks,
+        }
+
+        if highlighted_page_image:
+            response_data["highlighted_page_image"] = highlighted_page_image
+
+        return JSONResponse(response_data)
+
+    except Exception as e:
+        error_msg = _sanitize_error_for_client(e, "get_chunk_context")
+        return JSONResponse(
+            {"error": error_msg},
+            status_code=500,
+        )
+
+
+async def get_pdf_preview(request: Request) -> JSONResponse:
+    """GET /api/v1/pdf-preview - Render PDF page to PNG image.
+
+    Server-side PDF rendering using PyMuPDF. This endpoint allows Astrolabe
+    to display PDF pages without requiring client-side PDF.js, avoiding CSP
+    worker restrictions and ES private field issues in Chromium.
+
+    Query parameters:
+        file_path: WebDAV path to PDF file (e.g., "/Documents/report.pdf")
+        page: Page number (1-indexed, default: 1)
+        scale: Zoom factor for rendering (default: 2.0 = 144 DPI)
+
+    Returns:
+        {
+            "success": true,
+            "image": "<base64-encoded-png>",
+            "page_number": 1,
+            "total_pages": 10
+        }
+
+    Requires OAuth bearer token for authentication.
+    """
+    # Log incoming request
+    file_path_param = request.query_params.get("file_path", "<not provided>")
+    page_param = request.query_params.get("page", "1")
+    logger.info(f"PDF preview request: file_path={file_path_param}, page={page_param}")
+
+    try:
+        # Validate OAuth token and extract user
+        user_id, validated = await validate_token_and_get_user(request)
+        logger.info(f"PDF preview authenticated for user: {user_id}")
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/pdf-preview: {e}")
+        return JSONResponse(
+            {
+                "success": False,
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "get_pdf_preview"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Parse and validate parameters
+        file_path = request.query_params.get("file_path")
+        if not file_path:
+            return JSONResponse(
+                {"success": False, "error": "Missing required parameter: file_path"},
+                status_code=400,
+            )
+
+        # Validate no path traversal sequences
+        if ".." in file_path:
+            return JSONResponse(
+                {"success": False, "error": "Invalid file path"},
+                status_code=400,
+            )
+
+        try:
+            page_num = _parse_int_param(
+                request.query_params.get("page"), 1, 1, 10000, "page"
+            )
+            scale = _parse_float_param(
+                request.query_params.get("scale"), 2.0, 0.5, 5.0, "scale"
+            )
+        except ValueError as e:
+            return JSONResponse({"success": False, "error": str(e)}, status_code=400)
+
+        # Get bearer token for WebDAV authentication
+        token = extract_bearer_token(request)
+        if not token:
+            raise ValueError("Missing token")
+
+        # Get Nextcloud host from OAuth context
+        oauth_ctx = request.app.state.oauth_context
+        nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+        if not nextcloud_host:
+            raise ValueError("Nextcloud host not configured")
+
+        # Download PDF via WebDAV using user's token
+        async with NextcloudClient.from_token(
+            base_url=nextcloud_host, token=token, username=user_id
+        ) as nc_client:
+            pdf_bytes, _ = await nc_client.webdav.read_file(file_path)
+
+        # Check file size limit (50 MB)
+        max_pdf_size = 50 * 1024 * 1024
+        if len(pdf_bytes) > max_pdf_size:
+            return JSONResponse(
+                {
+                    "success": False,
+                    "error": f"PDF file exceeds maximum size limit ({max_pdf_size // (1024 * 1024)} MB)",
+                },
+                status_code=413,
+            )
+
+        # Render page with PyMuPDF
+        doc = pymupdf.open(stream=pdf_bytes, filetype="pdf")
+        try:
+            total_pages = doc.page_count
+
+            # Validate page number
+            if page_num > total_pages:
+                return JSONResponse(
+                    {
+                        "success": False,
+                        "error": f"Page {page_num} does not exist (document has {total_pages} pages)",
+                    },
+                    status_code=400,
+                )
+
+            page = doc[page_num - 1]  # 0-indexed
+            mat = pymupdf.Matrix(scale, scale)
+            pix = page.get_pixmap(matrix=mat, alpha=False)
+            png_bytes = pix.tobytes("png")
+        finally:
+            doc.close()
+
+        # Encode as base64
+        image_b64 = base64.b64encode(png_bytes).decode("ascii")
+
+        logger.info(
+            f"Rendered PDF preview: {file_path} page {page_num}/{total_pages}, "
+            f"{len(png_bytes):,} bytes"
+        )
+
+        return JSONResponse(
+            {
+                "success": True,
+                "image": image_b64,
+                "page_number": page_num,
+                "total_pages": total_pages,
+            }
+        )
+
+    except FileNotFoundError:
+        logger.warning(f"PDF file not found: {file_path_param}")
+        return JSONResponse(
+            {"success": False, "error": "PDF file not found"},
+            status_code=404,
+        )
+    except (pymupdf.FileDataError, pymupdf.EmptyFileError):
+        logger.warning(f"Invalid or corrupted PDF file: {file_path_param}")
+        return JSONResponse(
+            {"success": False, "error": "Invalid or corrupted PDF file"},
+            status_code=400,
+        )
+    except Exception as e:
+        logger.error(f"PDF preview error: {e}", exc_info=True)
+        error_msg = _sanitize_error_for_client(e, "get_pdf_preview")
+        return JSONResponse(
+            {"success": False, "error": error_msg},
+            status_code=500,
+        )

nextcloud_mcp_server/api/webhooks.py

@@ -0,0 +1,304 @@
+"""Webhook management API endpoints.
+
+Provides REST API endpoints for managing webhook registrations with Nextcloud.
+These endpoints are used by the Nextcloud PHP app (Astrolabe) to:
+- List installed Nextcloud apps
+- Create, list, and delete webhook registrations
+
+All endpoints require OAuth bearer token authentication via UnifiedTokenVerifier.
+"""
+
+import logging
+
+from starlette.requests import Request
+from starlette.responses import JSONResponse
+
+from nextcloud_mcp_server.api.management import (
+    _sanitize_error_for_client,
+    extract_bearer_token,
+    validate_token_and_get_user,
+)
+from nextcloud_mcp_server.client.webhooks import WebhooksClient
+
+from ..http import nextcloud_httpx_client
+
+logger = logging.getLogger(__name__)
+
+
+async def get_installed_apps(request: Request) -> JSONResponse:
+    """GET /api/v1/apps - Get list of installed Nextcloud apps.
+
+    Returns a list of installed app IDs for filtering webhook presets.
+
+    Requires OAuth bearer token for authentication.
+    """
+    try:
+        # Validate OAuth token and extract user
+        user_id, validated = await validate_token_and_get_user(request)
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/apps: {e}")
+        return JSONResponse(
+            {
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "get_installed_apps"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Get Bearer token from request
+        token = extract_bearer_token(request)
+        if not token:
+            raise ValueError("Missing Authorization header")
+
+        # Get Nextcloud host from OAuth context
+        oauth_ctx = request.app.state.oauth_context
+        nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+        if not nextcloud_host:
+            raise ValueError("Nextcloud host not configured")
+
+        # Create authenticated HTTP client
+        async with nextcloud_httpx_client(
+            base_url=nextcloud_host,
+            headers={"Authorization": f"Bearer {token}"},
+            timeout=30.0,
+        ) as client:
+            # Get installed apps using OCS API
+            # Notes, Calendar, Deck, Tables, etc. are apps that support webhooks
+            # We check which ones are installed and enabled
+            ocs_url = "/ocs/v1.php/cloud/apps"
+            params = {"filter": "enabled"}
+
+            response = await client.get(
+                ocs_url,
+                params=params,
+                headers={"OCS-APIRequest": "true", "Accept": "application/json"},
+            )
+
+            if response.status_code != 200:
+                raise ValueError(f"OCS API returned status {response.status_code}")
+
+            data = response.json()
+            apps = data.get("ocs", {}).get("data", {}).get("apps", [])
+
+            return JSONResponse({"apps": apps})
+
+    except Exception as e:
+        logger.error(f"Error getting installed apps for user {user_id}: {e}")
+        return JSONResponse(
+            {
+                "error": "Internal error",
+                "message": _sanitize_error_for_client(e, "get_installed_apps"),
+            },
+            status_code=500,
+        )
+
+
+async def list_webhooks(request: Request) -> JSONResponse:
+    """GET /api/v1/webhooks - List all registered webhooks.
+
+    Returns list of webhook registrations for the authenticated user.
+
+    Requires OAuth bearer token for authentication.
+    """
+    try:
+        # Validate OAuth token and extract user
+        user_id, validated = await validate_token_and_get_user(request)
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/webhooks: {e}")
+        return JSONResponse(
+            {
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "list_webhooks"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Get Bearer token from request
+        token = extract_bearer_token(request)
+        if not token:
+            raise ValueError("Missing Authorization header")
+
+        # Get Nextcloud host from OAuth context
+        oauth_ctx = request.app.state.oauth_context
+        nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+        if not nextcloud_host:
+            raise ValueError("Nextcloud host not configured")
+
+        # Create authenticated HTTP client
+        async with nextcloud_httpx_client(
+            base_url=nextcloud_host,
+            headers={"Authorization": f"Bearer {token}"},
+            timeout=30.0,
+        ) as client:
+            # Use WebhooksClient to list webhooks
+            webhooks_client = WebhooksClient(client, user_id)
+            webhooks = await webhooks_client.list_webhooks()
+
+            return JSONResponse({"webhooks": webhooks})
+
+    except Exception as e:
+        logger.error(f"Error listing webhooks for user {user_id}: {e}")
+        return JSONResponse(
+            {
+                "error": "Internal error",
+                "message": _sanitize_error_for_client(e, "list_webhooks"),
+            },
+            status_code=500,
+        )
+
+
+async def create_webhook(request: Request) -> JSONResponse:
+    """POST /api/v1/webhooks - Create a new webhook registration.
+
+    Request body:
+    {
+        "event": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+        "uri": "http://mcp:8000/webhooks/nextcloud",
+        "eventFilter": {"event.node.path": "/^\\/.*\\/files\\/Notes\\//"}
+    }
+
+    Returns the created webhook data including the webhook ID.
+
+    Requires OAuth bearer token for authentication.
+    """
+    try:
+        # Validate OAuth token and extract user
+        user_id, validated = await validate_token_and_get_user(request)
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/webhooks: {e}")
+        return JSONResponse(
+            {
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "create_webhook"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Parse request body
+        body = await request.json()
+        event = body.get("event")
+        uri = body.get("uri")
+        # Accept both camelCase (eventFilter) and snake_case (event_filter)
+        event_filter = body.get("eventFilter") or body.get("event_filter")
+
+        if not event or not uri:
+            return JSONResponse(
+                {
+                    "error": "Bad request",
+                    "message": "Missing required fields: event, uri",
+                },
+                status_code=400,
+            )
+
+        # Get Bearer token from request
+        token = extract_bearer_token(request)
+        if not token:
+            raise ValueError("Missing Authorization header")
+
+        # Get Nextcloud host from OAuth context
+        oauth_ctx = request.app.state.oauth_context
+        nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+        if not nextcloud_host:
+            raise ValueError("Nextcloud host not configured")
+
+        # Create authenticated HTTP client
+        async with nextcloud_httpx_client(
+            base_url=nextcloud_host,
+            headers={"Authorization": f"Bearer {token}"},
+            timeout=30.0,
+        ) as client:
+            # Use WebhooksClient to create webhook
+            webhooks_client = WebhooksClient(client, user_id)
+            webhook_data = await webhooks_client.create_webhook(
+                event=event, uri=uri, event_filter=event_filter
+            )
+
+            return JSONResponse({"webhook": webhook_data})
+
+    except Exception as e:
+        logger.error(f"Error creating webhook for user {user_id}: {e}")
+        return JSONResponse(
+            {
+                "error": "Internal error",
+                "message": _sanitize_error_for_client(e, "create_webhook"),
+            },
+            status_code=500,
+        )
+
+
+async def delete_webhook(request: Request) -> JSONResponse:
+    """DELETE /api/v1/webhooks/{webhook_id} - Delete a webhook registration.
+
+    Returns success/failure status.
+
+    Requires OAuth bearer token for authentication.
+    """
+    try:
+        # Validate OAuth token and extract user
+        user_id, validated = await validate_token_and_get_user(request)
+    except Exception as e:
+        logger.warning(f"Unauthorized access to /api/v1/webhooks: {e}")
+        return JSONResponse(
+            {
+                "error": "Unauthorized",
+                "message": _sanitize_error_for_client(e, "delete_webhook"),
+            },
+            status_code=401,
+        )
+
+    try:
+        # Get webhook_id from path parameter
+        webhook_id = request.path_params.get("webhook_id")
+        if not webhook_id:
+            return JSONResponse(
+                {"error": "Bad request", "message": "Missing webhook_id"},
+                status_code=400,
+            )
+
+        try:
+            webhook_id = int(webhook_id)
+        except ValueError:
+            return JSONResponse(
+                {"error": "Bad request", "message": "Invalid webhook_id"},
+                status_code=400,
+            )
+
+        # Get Bearer token from request
+        token = extract_bearer_token(request)
+        if not token:
+            raise ValueError("Missing Authorization header")
+
+        # Get Nextcloud host from OAuth context
+        oauth_ctx = request.app.state.oauth_context
+        nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+        if not nextcloud_host:
+            raise ValueError("Nextcloud host not configured")
+
+        # Create authenticated HTTP client
+        async with nextcloud_httpx_client(
+            base_url=nextcloud_host,
+            headers={"Authorization": f"Bearer {token}"},
+            timeout=30.0,
+        ) as client:
+            # Use WebhooksClient to delete webhook
+            webhooks_client = WebhooksClient(client, user_id)
+            await webhooks_client.delete_webhook(webhook_id=webhook_id)
+
+            return JSONResponse({"success": True, "message": "Webhook deleted"})
+
+    except Exception as e:
+        logger.error(f"Error deleting webhook for user {user_id}: {e}")
+        return JSONResponse(
+            {
+                "error": "Internal error",
+                "message": _sanitize_error_for_client(e, "delete_webhook"),
+            },
+            status_code=500,
+        )

nextcloud_mcp_server/auth/astrolabe_client.py

@@ -9,7 +9,7 @@ import logging
 import time
 from typing import Optional
 
-import httpx
+from ..http import nextcloud_httpx_client
 
 logger = logging.getLogger(__name__)
 
@@ -60,7 +60,7 @@ class AstrolabeClient:
         # Discover token endpoint
         discovery_url = f"{self.nextcloud_host}/.well-known/openid-configuration"
 
-        async with httpx.AsyncClient() as client:
+        async with nextcloud_httpx_client() as client:
             logger.debug(f"Discovering token endpoint from {discovery_url}")
             discovery_resp = await client.get(discovery_url)
             discovery_resp.raise_for_status()
@@ -107,7 +107,7 @@ class AstrolabeClient:
         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:
+        async with nextcloud_httpx_client() as client:
             logger.debug(f"Retrieving app password for user: {user_id}")
 
             response = await client.get(

nextcloud_mcp_server/auth/browser_oauth_routes.py

@@ -8,8 +8,10 @@ import hashlib
 import logging
 import os
 import secrets
+import time
 from base64 import urlsafe_b64encode
 from urllib.parse import urlencode
+from urllib.parse import urlparse as parse_url
 
 import httpx
 import jwt
@@ -21,6 +23,8 @@ from nextcloud_mcp_server.auth.userinfo_routes import (
     _query_idp_userinfo,
 )
 
+from ..http import nextcloud_httpx_client
+
 logger = logging.getLogger(__name__)
 
 
@@ -141,7 +145,7 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
             )
 
         # Fetch authorization endpoint
-        async with httpx.AsyncClient() as http_client:
+        async with nextcloud_httpx_client() as http_client:
             response = await http_client.get(discovery_url)
             response.raise_for_status()
             discovery = response.json()
@@ -150,8 +154,6 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
         # Replace internal Docker hostname with public URL
         public_issuer = os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL")
         if public_issuer:
-            from urllib.parse import urlparse as parse_url
-
             internal_parsed = parse_url(oauth_config["nextcloud_host"])
             auth_parsed = parse_url(authorization_endpoint)
 
@@ -285,7 +287,7 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
             if code_verifier:
                 token_params["code_verifier"] = code_verifier
 
-            async with httpx.AsyncClient() as http_client:
+            async with nextcloud_httpx_client() as http_client:
                 response = await http_client.post(
                     oauth_client.token_endpoint,
                     data=token_params,
@@ -295,31 +297,12 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
         else:
             # Integrated mode (Nextcloud OIDC)
             discovery_url = oauth_config.get("discovery_url")
-            async with httpx.AsyncClient() as http_client:
+            async with nextcloud_httpx_client() as http_client:
                 response = await http_client.get(discovery_url)
                 response.raise_for_status()
                 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,
@@ -332,7 +315,7 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
             if code_verifier:
                 token_params["code_verifier"] = code_verifier
 
-            async with httpx.AsyncClient() as http_client:
+            async with nextcloud_httpx_client() as http_client:
                 response = await http_client.post(
                     token_endpoint,
                     data=token_params,
@@ -400,8 +383,6 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
     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})"

nextcloud_mcp_server/auth/client_registration.py

@@ -10,6 +10,8 @@ import httpx
 
 from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 
+from ..http import nextcloud_httpx_client
+
 logger = logging.getLogger(__name__)
 
 
@@ -132,7 +134,7 @@ async def register_client(
     logger.info(f"Registering OAuth client with Nextcloud: {client_name}")
     logger.debug(f"Registration endpoint: {registration_endpoint}")
 
-    async with httpx.AsyncClient(timeout=30.0) as client:
+    async with nextcloud_httpx_client(timeout=30.0) as client:
         try:
             response = await client.post(
                 registration_endpoint,
@@ -229,7 +231,7 @@ async def delete_client(
     logger.info(f"Deleting OAuth client: {client_id[:16]}...")
     logger.debug(f"Deletion endpoint: {deletion_endpoint}")
 
-    async with httpx.AsyncClient(timeout=30.0) as http_client:
+    async with nextcloud_httpx_client(timeout=30.0) as http_client:
         for attempt in range(max_retries):
             try:
                 # Prefer RFC 7592 Bearer token authentication

nextcloud_mcp_server/auth/client_registry.py

@@ -10,6 +10,7 @@ import logging
 import os
 from dataclasses import dataclass
 from typing import Dict, List, Optional
+from urllib.parse import urlparse
 
 logger = logging.getLogger(__name__)
 
@@ -161,8 +162,6 @@ class ClientRegistry:
             True if valid, False otherwise
         """
         # Parse the redirect URI
-        from urllib.parse import urlparse
-
         parsed = urlparse(redirect_uri)
 
         # Check against registered patterns

nextcloud_mcp_server/auth/keycloak_oauth.py

@@ -8,6 +8,7 @@ Handles OAuth flows with Keycloak as the identity provider, including:
 - Integration with RefreshTokenStorage
 """
 
+import base64
 import hashlib
 import logging
 import os
@@ -17,6 +18,8 @@ from urllib.parse import urlencode, urlparse
 
 import httpx
 
+from ..http import nextcloud_httpx_client
+
 logger = logging.getLogger(__name__)
 
 
@@ -106,7 +109,7 @@ class KeycloakOAuthClient:
     async def _get_http_client(self) -> httpx.AsyncClient:
         """Get or create HTTP client"""
         if self._http_client is None:
-            self._http_client = httpx.AsyncClient(timeout=30.0)
+            self._http_client = nextcloud_httpx_client(timeout=30.0)
         return self._http_client
 
     async def close(self) -> None:
@@ -155,7 +158,6 @@ class KeycloakOAuthClient:
         Returns:
             Tuple of (code_verifier, code_challenge)
         """
-        import base64
 
         # Generate code verifier (43-128 characters)
         code_verifier = secrets.token_urlsafe(32)

nextcloud_mcp_server/auth/oauth_routes.py

@@ -23,17 +23,21 @@ import hashlib
 import logging
 import os
 import secrets
+import time
 from base64 import urlsafe_b64encode
 from urllib.parse import urlencode
+from urllib.parse import urlparse as parse_url
 
-import httpx
 import jwt
 from starlette.requests import Request
-from starlette.responses import JSONResponse, RedirectResponse
+from starlette.responses import HTMLResponse, JSONResponse, RedirectResponse
 
+from nextcloud_mcp_server.auth.browser_oauth_routes import oauth_login_callback
 from nextcloud_mcp_server.auth.client_registry import get_client_registry
 from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 
+from ..http import nextcloud_httpx_client
+
 logger = logging.getLogger(__name__)
 
 
@@ -217,7 +221,7 @@ async def oauth_authorize(request: Request) -> RedirectResponse | JSONResponse:
             )
 
         # Fetch authorization endpoint from discovery
-        async with httpx.AsyncClient() as http_client:
+        async with nextcloud_httpx_client() as http_client:
             response = await http_client.get(discovery_url)
             response.raise_for_status()
             discovery = response.json()
@@ -226,8 +230,6 @@ async def oauth_authorize(request: Request) -> RedirectResponse | JSONResponse:
         # IMPORTANT: Replace internal Docker hostname with public URL for browser access
         # The discovery endpoint returns http://app/apps/oidc/authorize (internal)
         # But browsers need http://localhost:8080/apps/oidc/authorize (public)
-        from urllib.parse import urlparse as parse_url
-
         public_issuer = os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL")
         if public_issuer:
             # Parse internal and authorization endpoint to compare hostnames
@@ -353,7 +355,7 @@ async def oauth_authorize_nextcloud(
             status_code=500,
         )
 
-    async with httpx.AsyncClient() as http_client:
+    async with nextcloud_httpx_client() as http_client:
         response = await http_client.get(discovery_url)
         response.raise_for_status()
         discovery = response.json()
@@ -362,8 +364,6 @@ async def oauth_authorize_nextcloud(
     # Fix internal hostname for browser access
     public_issuer = os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL")
     if public_issuer:
-        from urllib.parse import urlparse as parse_url
-
         internal_parsed = parse_url(oauth_config["nextcloud_host"])
         auth_parsed = parse_url(authorization_endpoint)
 
@@ -461,7 +461,7 @@ async def oauth_callback_nextcloud(request: Request):
     callback_uri = f"{mcp_server_url}/oauth/callback"
 
     discovery_url = oauth_config.get("discovery_url")
-    async with httpx.AsyncClient() as http_client:
+    async with nextcloud_httpx_client() as http_client:
         response = await http_client.get(discovery_url)
         response.raise_for_status()
         discovery = response.json()
@@ -481,7 +481,7 @@ async def oauth_callback_nextcloud(request: Request):
         token_params["code_verifier"] = code_verifier
 
     # Exchange code for tokens
-    async with httpx.AsyncClient() as http_client:
+    async with nextcloud_httpx_client() as http_client:
         response = await http_client.post(
             token_endpoint,
             data=token_params,
@@ -521,8 +521,6 @@ async def oauth_callback_nextcloud(request: Request):
         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}")
@@ -567,8 +565,6 @@ async def oauth_callback_nextcloud(request: Request):
     </html>
     """
 
-    from starlette.responses import HTMLResponse
-
     return HTMLResponse(content=success_html, status_code=200)
 
 
@@ -633,10 +629,6 @@ async def oauth_callback(request: Request):
     elif flow_type == "browser":
         # Browser UI Login - establish browser session for /user/page access
         logger.info("Routing to browser login flow")
-        from nextcloud_mcp_server.auth.browser_oauth_routes import (
-            oauth_login_callback,
-        )
-
         return await oauth_login_callback(request)
 
     else:

nextcloud_mcp_server/auth/provisioning_decorator.py

@@ -9,11 +9,13 @@ import functools
 import logging
 from typing import Callable
 
+import jwt
 from mcp.server.fastmcp import Context
 from mcp.shared.exceptions import McpError
 from mcp.types import ErrorData
 
 from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+from nextcloud_mcp_server.config import get_settings
 
 logger = logging.getLogger(__name__)
 
@@ -65,8 +67,6 @@ def require_provisioning(func: Callable) -> Callable:
 
         # Check if we're in token exchange mode - if so, skip provisioning check
         # In token exchange mode, tokens are exchanged per-request (no stored refresh tokens)
-        from nextcloud_mcp_server.config import get_settings
-
         settings = get_settings()
         if hasattr(lifespan_ctx, "nextcloud_host") and settings.enable_token_exchange:
             # Token exchange mode - per-request exchange, no provisioning needed
@@ -78,8 +78,6 @@ def require_provisioning(func: Callable) -> Callable:
         user_id = None
         if hasattr(ctx, "authorization") and ctx.authorization:
             try:
-                import jwt
-
                 token = ctx.authorization.token
                 payload = jwt.decode(token, options={"verify_signature": False})
                 user_id = payload.get("sub")
@@ -163,8 +161,6 @@ def require_provisioning_or_suggest(func: Callable) -> Callable:
                 # Get user_id from authorization token
                 user_id = None
                 if hasattr(ctx, "authorization") and ctx.authorization:
-                    import jwt
-
                     token = ctx.authorization.token
                     payload = jwt.decode(token, options={"verify_signature": False})
                     user_id = payload.get("sub")

nextcloud_mcp_server/auth/scope_authorization.py

@@ -1,7 +1,6 @@
 """Scope-based authorization for MCP tools."""
 
 import logging
-import os
 from functools import wraps
 from typing import Any, Callable
 
@@ -10,6 +9,8 @@ from mcp.server.auth.provider import AccessToken
 from mcp.server.fastmcp import Context
 from mcp.server.fastmcp.utilities.context_injection import find_context_parameter
 
+from nextcloud_mcp_server.config import get_settings
+
 logger = logging.getLogger(__name__)
 
 
@@ -131,9 +132,10 @@ def require_scopes(*required_scopes: str):
             required_scopes_set = set(required_scopes)
 
             # Check if offline access is enabled
-            enable_offline_access = (
-                os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() == "true"
-            )
+            # Use settings.enable_offline_access which handles both ENABLE_BACKGROUND_OPERATIONS (new)
+            # and ENABLE_OFFLINE_ACCESS (deprecated) environment variables
+            settings = get_settings()
+            enable_offline_access = settings.enable_offline_access
 
             # In offline access mode, check if Nextcloud scopes require provisioning
             if enable_offline_access:

nextcloud_mcp_server/auth/storage.py

@@ -28,13 +28,18 @@ Sensitive data (tokens, secrets) is encrypted at rest using Fernet symmetric enc
 import json
 import logging
 import os
+import socket
 import time
 from pathlib import Path
 from typing import Any, Optional
 
 import aiosqlite
+import anyio
+import httpx
+from anyio import to_thread
 from cryptography.fernet import Fernet
 
+from nextcloud_mcp_server.migrations import stamp_database, upgrade_database
 from nextcloud_mcp_server.observability.metrics import record_db_operation
 
 logger = logging.getLogger(__name__)
@@ -163,10 +168,6 @@ class RefreshTokenStorage:
 
         # 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
@@ -830,7 +831,6 @@ class RefreshTokenStorage:
             resource_id: Resource identifier
             auth_method: Authentication method used
         """
-        import socket
 
         hostname = socket.gethostname()
         timestamp = int(time.time())
@@ -1240,6 +1240,243 @@ class RefreshTokenStorage:
 
         return deleted
 
+    # ============================================================================
+    # App Password Storage (multi-user BasicAuth mode)
+    # ============================================================================
+
+    async def store_app_password(
+        self,
+        user_id: str,
+        app_password: str,
+    ) -> None:
+        """
+        Store encrypted app password for background sync (multi-user BasicAuth mode).
+
+        Args:
+            user_id: Nextcloud user ID
+            app_password: Nextcloud app password to store
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        if not self.cipher:
+            raise RuntimeError(
+                "Encryption key not configured. "
+                "Set TOKEN_ENCRYPTION_KEY for app password storage."
+            )
+
+        encrypted_password = self.cipher.encrypt(app_password.encode())
+        now = int(time.time())
+
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                await db.execute(
+                    """
+                    INSERT OR REPLACE INTO app_passwords
+                    (user_id, encrypted_password, created_at, updated_at)
+                    VALUES (
+                        ?,
+                        ?,
+                        COALESCE((SELECT created_at FROM app_passwords WHERE user_id = ?), ?),
+                        ?
+                    )
+                    """,
+                    (user_id, encrypted_password, user_id, now, now),
+                )
+                await db.commit()
+
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "insert", duration, "success")
+            logger.info(f"Stored app password for user {user_id}")
+
+        except Exception:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "insert", duration, "error")
+            raise
+
+        # Audit log
+        await self._audit_log(
+            event="store_app_password",
+            user_id=user_id,
+            auth_method="app_password",
+        )
+
+    async def get_app_password(self, user_id: str) -> Optional[str]:
+        """
+        Retrieve and decrypt app password for a user.
+
+        Args:
+            user_id: Nextcloud user ID
+
+        Returns:
+            Decrypted app password, or None if not found
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        if not self.cipher:
+            raise RuntimeError(
+                "Encryption key not configured. "
+                "Set TOKEN_ENCRYPTION_KEY for app password retrieval."
+            )
+
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                async with db.execute(
+                    "SELECT encrypted_password FROM app_passwords WHERE user_id = ?",
+                    (user_id,),
+                ) as cursor:
+                    row = await cursor.fetchone()
+
+            if not row:
+                logger.debug(f"No app password found for user {user_id}")
+                duration = time.time() - start_time
+                record_db_operation("sqlite", "select", duration, "success")
+                return None
+
+            encrypted_password = row[0]
+            decrypted_password = self.cipher.decrypt(encrypted_password).decode()
+
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "select", duration, "success")
+            logger.debug(f"Retrieved app password for user {user_id}")
+
+            return decrypted_password
+
+        except Exception as e:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "select", duration, "error")
+            logger.error(f"Failed to decrypt app password for user {user_id}: {e}")
+            return None
+
+    async def delete_app_password(self, user_id: str) -> bool:
+        """
+        Delete app password for a user.
+
+        Args:
+            user_id: Nextcloud user ID
+
+        Returns:
+            True if password was deleted, False if not found
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                cursor = await db.execute(
+                    "DELETE FROM app_passwords WHERE user_id = ?",
+                    (user_id,),
+                )
+                await db.commit()
+                deleted = cursor.rowcount > 0
+
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "delete", duration, "success")
+
+            if deleted:
+                logger.info(f"Deleted app password for user {user_id}")
+                await self._audit_log(
+                    event="delete_app_password",
+                    user_id=user_id,
+                    auth_method="app_password",
+                )
+            else:
+                logger.debug(f"No app password to delete for user {user_id}")
+
+            return deleted
+
+        except Exception:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "delete", duration, "error")
+            raise
+
+    async def get_all_app_password_user_ids(self) -> list[str]:
+        """
+        Get list of all user IDs with stored app passwords.
+
+        Returns:
+            List of user IDs
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        async with aiosqlite.connect(self.db_path) as db:
+            async with db.execute(
+                "SELECT user_id FROM app_passwords ORDER BY updated_at DESC"
+            ) as cursor:
+                rows = await cursor.fetchall()
+
+        user_ids = [row[0] for row in rows]
+        logger.debug(f"Found {len(user_ids)} users with app passwords")
+        return user_ids
+
+    async def cleanup_invalid_app_passwords(self, nextcloud_host: str) -> list[str]:
+        """
+        Validate stored app passwords against Nextcloud and remove invalid ones.
+
+        Makes a lightweight OCS request for each stored user to check if credentials
+        are still valid. Removes entries that return 401/403.
+
+        Args:
+            nextcloud_host: Nextcloud base URL
+
+        Returns:
+            List of user IDs whose app passwords were removed
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        user_ids = await self.get_all_app_password_user_ids()
+        if not user_ids:
+            return []
+
+        removed: list[str] = []
+
+        async def _validate_user(user_id: str) -> None:
+            app_password = await self.get_app_password(user_id)
+            if not app_password:
+                return
+
+            try:
+                async with httpx.AsyncClient(
+                    base_url=nextcloud_host,
+                    auth=httpx.BasicAuth(user_id, app_password),
+                    timeout=10.0,
+                ) as client:
+                    response = await client.get(
+                        "/ocs/v2.php/cloud/user",
+                        headers={
+                            "OCS-APIRequest": "true",
+                            "Accept": "application/json",
+                        },
+                    )
+
+                if response.status_code in (401, 403):
+                    logger.info(
+                        f"App password for {user_id} is invalid "
+                        f"(HTTP {response.status_code}), removing"
+                    )
+                    await self.delete_app_password(user_id)
+                    removed.append(user_id)
+                else:
+                    logger.debug(
+                        f"App password for {user_id} validated "
+                        f"(HTTP {response.status_code})"
+                    )
+
+            except Exception as e:
+                logger.warning(f"Could not validate app password for {user_id}: {e}")
+
+        async with anyio.create_task_group() as tg:
+            for user_id in user_ids:
+                tg.start_soon(_validate_user, user_id)
+
+        return removed
+
 
 async def generate_encryption_key() -> str:
     """

nextcloud_mcp_server/auth/token_broker.py

@@ -25,6 +25,8 @@ import jwt
 from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.auth.token_exchange import exchange_token_for_delegation
 
+from ..http import nextcloud_httpx_client
+
 logger = logging.getLogger(__name__)
 
 
@@ -136,7 +138,7 @@ class TokenBrokerService:
     async def _get_http_client(self) -> httpx.AsyncClient:
         """Get or create HTTP client."""
         if self._http_client is None:
-            self._http_client = httpx.AsyncClient(
+            self._http_client = nextcloud_httpx_client(
                 timeout=httpx.Timeout(30.0), follow_redirects=True
             )
         return self._http_client
@@ -168,37 +170,6 @@ 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.
@@ -407,7 +378,7 @@ class TokenBrokerService:
             Tuple of (access_token, expires_in_seconds)
         """
         config = await self._get_oidc_config()
-        token_endpoint = self._rewrite_token_endpoint(config["token_endpoint"])
+        token_endpoint = config["token_endpoint"]
 
         client = await self._get_http_client()
 
@@ -477,7 +448,7 @@ class TokenBrokerService:
             Tuple of (access_token, expires_in_seconds)
         """
         config = await self._get_oidc_config()
-        token_endpoint = self._rewrite_token_endpoint(config["token_endpoint"])
+        token_endpoint = config["token_endpoint"]
 
         client = await self._get_http_client()
 

nextcloud_mcp_server/auth/token_exchange.py

@@ -20,6 +20,7 @@ import httpx
 import jwt
 
 from ..config import get_settings
+from ..http import nextcloud_httpx_client
 from .storage import RefreshTokenStorage
 
 logger = logging.getLogger(__name__)
@@ -68,7 +69,7 @@ class TokenExchangeService:
         self.storage: Optional[RefreshTokenStorage] = None
 
         # Create HTTP client
-        self.http_client = httpx.AsyncClient(
+        self.http_client = nextcloud_httpx_client(
             timeout=30.0,
             follow_redirects=True,
         )

nextcloud_mcp_server/auth/unified_verifier.py

@@ -31,6 +31,8 @@ from nextcloud_mcp_server.observability.metrics import (
     record_oauth_token_validation,
 )
 
+from ..http import nextcloud_httpx_client
+
 logger = logging.getLogger(__name__)
 
 
@@ -61,7 +63,7 @@ class UnifiedTokenVerifier(TokenVerifier):
         self.mode = "exchange" if settings.enable_token_exchange else "multi-audience"
 
         # Common components for all modes
-        self.http_client = httpx.AsyncClient(timeout=10.0)
+        self.http_client = nextcloud_httpx_client(timeout=10.0)
 
         # JWT verification support
         self.jwks_client: PyJWKClient | None = None
@@ -117,6 +119,71 @@ class UnifiedTokenVerifier(TokenVerifier):
         # Both modes do the same validation (MCP audience only)
         return await self._verify_mcp_audience(token)
 
+    async def verify_token_for_management_api(self, token: str) -> AccessToken | None:
+        """
+        Verify token for management API access (ADR-018 NC PHP app integration).
+
+        This verification accepts ANY valid Nextcloud OIDC token, not just tokens
+        with MCP server audience. This is needed because:
+        - Astrolabe (NC PHP app) uses its own OAuth client with Nextcloud OIDC
+        - Tokens from Astrolabe have Astrolabe's client_id as audience
+        - MCP server's management API should accept these tokens
+
+        Security Model:
+        ~~~~~~~~~~~~~~~~
+        This relaxed audience validation is secure because:
+
+        1. **Authentication layer** (this method):
+           - Verifies token signature against Nextcloud's JWKS (cryptographic proof)
+           - Verifies token is not expired
+           - Extracts user identity from validated token claims
+
+        2. **Authorization layer** (management API endpoints):
+           - EVERY endpoint verifies: token.sub == requested_resource_owner
+           - Example: GET /users/{user_id}/session checks token_user_id == path_user_id
+           - Users can ONLY access their own resources, never another user's
+
+        3. **Attack scenario analysis**:
+           - Attacker with stolen token for App A cannot access user B's data
+           - Token's `sub` claim is cryptographically bound to a specific user
+           - Authorization layer rejects cross-user access attempts (403 Forbidden)
+
+        4. **Why audience validation isn't needed here**:
+           - Audience validation prevents token confusion attacks across services
+           - But management API authorization already gates access per-user
+           - A token valid for "astrolabe" is still bound to user X, not user Y
+
+        Args:
+            token: Bearer token to verify
+
+        Returns:
+            AccessToken if valid (regardless of audience), None otherwise
+        """
+        # Check cache first (using separate cache key to avoid mixing with MCP tokens)
+        cache_key = f"mgmt:{hashlib.sha256(token.encode()).hexdigest()}"
+        if cache_key in self._token_cache:
+            userinfo, expiry = self._token_cache[cache_key]
+            if time.time() < expiry:
+                logger.debug("Management API token found in cache")
+                oauth_token_cache_hits_total.labels(hit="true").inc()
+                username = userinfo.get("sub") or userinfo.get("preferred_username")
+                scope_string = userinfo.get("scope", "")
+                scopes = scope_string.split() if scope_string else []
+                return AccessToken(
+                    token=token,
+                    client_id=userinfo.get("client_id", ""),
+                    scopes=scopes,
+                    expires_at=int(expiry),
+                    resource=username,
+                )
+            else:
+                del self._token_cache[cache_key]
+
+        oauth_token_cache_hits_total.labels(hit="false").inc()
+
+        # Verify token without audience check
+        return await self._verify_without_audience_check(token, cache_key)
+
     async def _verify_mcp_audience(self, token: str) -> AccessToken | None:
         """
         Validate token has MCP audience.
@@ -186,6 +253,78 @@ class UnifiedTokenVerifier(TokenVerifier):
             record_oauth_token_validation(validation_method, "error")
             return None
 
+    async def _verify_without_audience_check(
+        self, token: str, cache_key: str
+    ) -> AccessToken | None:
+        """
+        Verify token validity without checking MCP audience or issuer.
+
+        Used for management API where tokens from Astrolabe (NC PHP app) need to
+        be accepted. These tokens are issued by Nextcloud OIDC to Astrolabe's
+        OAuth client, not MCP server's client.
+
+        What we verify:
+        - ✓ Token signature (cryptographic proof token is from Nextcloud OIDC)
+        - ✓ Token expiration (not expired)
+        - ✓ Token structure (valid JWT format)
+
+        What we skip:
+        - ✗ Audience check (token may have Astrolabe's audience, not MCP's)
+        - ✗ Issuer check (token may have internal Nextcloud URL as issuer)
+
+        Security guarantee:
+        - Authorization is enforced by management API endpoints
+        - Each endpoint verifies: token.sub == requested_resource_owner
+        - See verify_token_for_management_api() docstring for full security model
+
+        Args:
+            token: Bearer token to verify
+            cache_key: Cache key for storing validation result
+
+        Returns:
+            AccessToken if valid, None otherwise
+        """
+        validation_method = "unknown"
+        try:
+            # Attempt JWT verification first
+            # Skip issuer check for management API tokens (may have internal URL)
+            if self._is_jwt_format(token) and self.jwks_client:
+                validation_method = "jwt"
+                payload = await self._verify_jwt_signature(
+                    token, skip_issuer_check=True
+                )
+                if payload:
+                    record_oauth_token_validation("jwt", "valid")
+                else:
+                    record_oauth_token_validation("jwt", "invalid")
+                    return None
+            else:
+                # Fall back to introspection for opaque tokens
+                validation_method = "introspect"
+                payload = await self._introspect_token(token)
+                if payload:
+                    record_oauth_token_validation("introspect", "valid")
+                else:
+                    record_oauth_token_validation("introspect", "invalid")
+                    return None
+
+            # Check payload is valid
+            if not payload:
+                return None
+
+            # Skip audience validation - any valid Nextcloud token is accepted
+            logger.debug(
+                f"Management API token validated (no audience check) for user: {payload.get('sub')}"
+            )
+
+            # Cache and return the token
+            return self._create_access_token_with_cache_key(token, payload, cache_key)
+
+        except Exception as e:
+            logger.error(f"Management API token verification failed: {e}")
+            record_oauth_token_validation(validation_method, "error")
+            return None
+
     def _has_mcp_audience(self, payload: dict[str, Any]) -> bool:
         """
         Check if token has MCP audience.
@@ -230,12 +369,15 @@ class UnifiedTokenVerifier(TokenVerifier):
         """
         return "." in token and token.count(".") == 2
 
-    async def _verify_jwt_signature(self, token: str) -> dict[str, Any] | None:
+    async def _verify_jwt_signature(
+        self, token: str, skip_issuer_check: bool = False
+    ) -> dict[str, Any] | None:
         """
         Verify JWT token with signature validation using JWKS.
 
         Args:
             token: JWT token to verify
+            skip_issuer_check: If True, skip issuer validation (for management API tokens)
 
         Returns:
             Decoded payload if valid, None if invalid
@@ -248,25 +390,22 @@ class UnifiedTokenVerifier(TokenVerifier):
 
             # Verify and decode JWT
             # Note: We don't validate audience here - that's done separately based on mode
+            # Issuer validation can be skipped for management API tokens (from Astrolabe)
+            should_verify_issuer = (
+                not skip_issuer_check
+                and hasattr(self.settings, "oidc_issuer")
+                and self.settings.oidc_issuer
+            )
             payload = jwt.decode(
                 token,
                 signing_key.key,
                 algorithms=["RS256"],
-                issuer=(
-                    self.settings.oidc_issuer
-                    if hasattr(self.settings, "oidc_issuer")
-                    else None
-                ),
+                issuer=(self.settings.oidc_issuer if should_verify_issuer else None),
                 options={
                     "verify_signature": True,
                     "verify_exp": True,
                     "verify_iat": True,
-                    "verify_iss": (
-                        True
-                        if hasattr(self.settings, "oidc_issuer")
-                        and self.settings.oidc_issuer
-                        else False
-                    ),
+                    "verify_iss": should_verify_issuer,
                     "verify_aud": False,  # We handle audience validation separately
                 },
             )
@@ -358,6 +497,24 @@ class UnifiedTokenVerifier(TokenVerifier):
             token: The bearer token
             payload: Validated token payload
 
+        Returns:
+            AccessToken object or None if required fields missing
+        """
+        # Use default cache key (hash of token)
+        cache_key = hashlib.sha256(token.encode()).hexdigest()
+        return self._create_access_token_with_cache_key(token, payload, cache_key)
+
+    def _create_access_token_with_cache_key(
+        self, token: str, payload: dict[str, Any], cache_key: str
+    ) -> AccessToken | None:
+        """
+        Create AccessToken object from validated token payload with custom cache key.
+
+        Args:
+            token: The bearer token
+            payload: Validated token payload
+            cache_key: Key to use for caching (allows separate caches for MCP vs management API)
+
         Returns:
             AccessToken object or None if required fields missing
         """
@@ -382,14 +539,13 @@ class UnifiedTokenVerifier(TokenVerifier):
             logger.warning("No 'exp' claim in token, using default TTL")
             exp = int(time.time() + self.cache_ttl)
 
-        # Cache the result
-        token_hash = hashlib.sha256(token.encode()).hexdigest()
+        # Cache the result with the provided key
         userinfo = {
             "sub": username,
             "scope": scope_string,
             **{k: v for k, v in payload.items() if k not in ["sub", "scope"]},
         }
-        self._token_cache[token_hash] = (userinfo, exp)
+        self._token_cache[cache_key] = (userinfo, exp)
 
         return AccessToken(
             token=token,

nextcloud_mcp_server/auth/userinfo_routes.py

@@ -9,16 +9,21 @@ For OAuth mode: Requires browser-based OAuth login to establish session.
 
 import logging
 import os
+import traceback
 from pathlib import Path
 from typing import Any
 
-import httpx
+from httpx import BasicAuth
 from jinja2 import Environment, FileSystemLoader
 from starlette.authentication import requires
 from starlette.requests import Request
 from starlette.responses import HTMLResponse, JSONResponse
 
+from nextcloud_mcp_server.auth.permissions import is_nextcloud_admin
 from nextcloud_mcp_server.client import NextcloudClient
+from nextcloud_mcp_server.config import get_settings
+
+from ..http import nextcloud_httpx_client
 
 logger = logging.getLogger(__name__)
 
@@ -53,8 +58,6 @@ async def _get_authenticated_client_for_userinfo(request: Request) -> NextcloudC
         if not all([nextcloud_host, username, password]):
             raise RuntimeError("BasicAuth credentials not configured")
 
-        from httpx import BasicAuth
-
         assert nextcloud_host is not None
         assert username is not None
         assert password is not None
@@ -105,9 +108,9 @@ async def _get_processing_status(request: Request) -> dict[str, Any] | None:
             "status": str,  # "syncing" or "idle"
         }
     """
-    # Check if vector sync is enabled
-    vector_sync_enabled = os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
-    if not vector_sync_enabled:
+    # Check if vector sync is enabled (supports both old and new env var names)
+    settings = get_settings()
+    if not settings.vector_sync_enabled:
         return None
 
     try:
@@ -126,10 +129,10 @@ async def _get_processing_status(request: Request) -> dict[str, Any] | None:
         # Get Qdrant client and query indexed count
         indexed_count = 0
         try:
-            from nextcloud_mcp_server.config import get_settings
-            from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
+            from nextcloud_mcp_server.vector.qdrant_client import (  # noqa: PLC0415
+                get_qdrant_client,
+            )
 
-            settings = get_settings()
             qdrant_client = await get_qdrant_client()
 
             # Count documents in collection
@@ -257,7 +260,7 @@ async def _get_userinfo_endpoint(oauth_ctx: dict[str, Any]) -> str | None:
         return None
 
     try:
-        async with httpx.AsyncClient(timeout=10.0) as client:
+        async with nextcloud_httpx_client(timeout=10.0) as client:
             response = await client.get(discovery_url)
             response.raise_for_status()
             discovery = response.json()
@@ -290,7 +293,7 @@ async def _query_idp_userinfo(
         User info dictionary from IdP, or None if query fails
     """
     try:
-        async with httpx.AsyncClient(timeout=10.0) as client:
+        async with nextcloud_httpx_client(timeout=10.0) as client:
             response = await client.get(
                 userinfo_uri,
                 headers={"Authorization": f"Bearer {access_token_str}"},
@@ -385,8 +388,6 @@ async def _get_user_info(request: Request) -> dict[str, Any]:
         return user_context
 
     except Exception as e:
-        import traceback
-
         logger.error(f"Error retrieving user info: {e}")
         logger.error(f"Traceback: {traceback.format_exc()}")
         return {
@@ -432,8 +433,6 @@ async def user_info_html(request: Request) -> HTMLResponse:
     # Check if user is admin (for Webhooks tab)
     is_admin = False
     try:
-        from nextcloud_mcp_server.auth.permissions import is_nextcloud_admin
-
         # Get authenticated Nextcloud client
         nc_client = await _get_authenticated_client_for_userinfo(request)
         is_admin = await is_nextcloud_admin(request, nc_client._client)
@@ -472,8 +471,6 @@ async def user_info_html(request: Request) -> HTMLResponse:
     # Get Nextcloud host for generating links to apps (used by viz tab)
     # Use public issuer URL if available (for browser-accessible links),
     # otherwise fall back to NEXTCLOUD_HOST from settings
-    from nextcloud_mcp_server.config import get_settings
-
     settings = get_settings()
     nextcloud_host_for_links = (
         os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL") or settings.nextcloud_host
@@ -635,7 +632,9 @@ async def user_info_html(request: Request) -> HTMLResponse:
         """
 
     # Check if vector sync is enabled (needed for Welcome tab)
-    vector_sync_enabled = os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
+    # Note: get_settings() supports both ENABLE_SEMANTIC_SEARCH and VECTOR_SYNC_ENABLED
+    settings = get_settings()
+    vector_sync_enabled = settings.vector_sync_enabled
 
     # Render template
     template = _jinja_env.get_template("user_info.html")

nextcloud_mcp_server/auth/viz_routes.py

@@ -15,18 +15,25 @@ import logging
 import time
 from pathlib import Path
 
+import anyio
 import numpy as np
 from jinja2 import Environment, FileSystemLoader
+from qdrant_client.models import FieldCondition, Filter, MatchValue
 from starlette.authentication import requires
 from starlette.requests import Request
 from starlette.responses import HTMLResponse, JSONResponse
 
+from nextcloud_mcp_server.auth.userinfo_routes import (
+    _get_authenticated_client_for_userinfo,
+)
 from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.embedding.service import get_embedding_service
 from nextcloud_mcp_server.observability.tracing import trace_operation
 from nextcloud_mcp_server.search import (
     BM25HybridSearchAlgorithm,
     SemanticSearchAlgorithm,
 )
+from nextcloud_mcp_server.search.context import get_chunk_with_context
 from nextcloud_mcp_server.vector.pca import PCA
 from nextcloud_mcp_server.vector.placeholder import get_placeholder_filter
 from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
@@ -136,10 +143,6 @@ async def vector_visualization_search(request: Request) -> JSONResponse:
         # Get authenticated HTTP client from session
         # In BasicAuth mode: uses username/password from session
         # In OAuth mode: uses access token from session
-        from nextcloud_mcp_server.auth.userinfo_routes import (
-            _get_authenticated_client_for_userinfo,
-        )
-
         with trace_operation("vector_viz.get_auth_client"):
             auth_client_ctx = await _get_authenticated_client_for_userinfo(request)
 
@@ -352,8 +355,6 @@ async def vector_visualization_search(request: Request) -> JSONResponse:
             )
         else:
             # Fallback: generate embedding if not available from search
-            from nextcloud_mcp_server.embedding.service import get_embedding_service
-
             embedding_service = get_embedding_service()
             query_embedding = await embedding_service.embed(query)
             logger.info(f"Generated query embedding (dimension={len(query_embedding)})")
@@ -396,8 +397,6 @@ async def vector_visualization_search(request: Request) -> JSONResponse:
             coords = pca.fit_transform(vectors)
             return coords, pca
 
-        import anyio
-
         with trace_operation(
             "vector_viz.pca_compute",
             attributes={
@@ -556,11 +555,6 @@ async def chunk_context_endpoint(request: Request) -> JSONResponse:
         doc_id_int = int(doc_id)
 
         # Get authenticated Nextcloud client
-        from nextcloud_mcp_server.auth.userinfo_routes import (
-            _get_authenticated_client_for_userinfo,
-        )
-        from nextcloud_mcp_server.search.context import get_chunk_with_context
-
         # Use context expansion module to fetch chunk with surrounding context
         async with await _get_authenticated_client_for_userinfo(request) as nc_client:
             chunk_context = await get_chunk_with_context(
@@ -595,8 +589,6 @@ async def chunk_context_endpoint(request: Request) -> JSONResponse:
         page_number = None
         if doc_type == "file":
             try:
-                from qdrant_client.models import FieldCondition, Filter, MatchValue
-
                 settings = get_settings()
                 qdrant_client = await get_qdrant_client()
                 username = request.user.display_name

nextcloud_mcp_server/auth/webhook_routes.py

@@ -20,6 +20,8 @@ from nextcloud_mcp_server.server.webhook_presets import (
     get_preset,
 )
 
+from ..http import nextcloud_httpx_client
+
 logger = logging.getLogger(__name__)
 
 
@@ -140,7 +142,7 @@ async def _get_authenticated_client(request: Request) -> httpx.AsyncClient:
 
         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(
+        return nextcloud_httpx_client(
             base_url=nextcloud_host,
             auth=(username, password),
             timeout=30.0,
@@ -163,7 +165,7 @@ async def _get_authenticated_client(request: Request) -> httpx.AsyncClient:
     if not nextcloud_host:
         raise RuntimeError("Nextcloud host not configured")
 
-    return httpx.AsyncClient(
+    return nextcloud_httpx_client(
         base_url=nextcloud_host,
         headers={"Authorization": f"Bearer {access_token}"},
         timeout=30.0,

nextcloud_mcp_server/cli.py

@@ -6,6 +6,13 @@ import uvicorn
 from nextcloud_mcp_server.config import (
     get_settings,
 )
+from nextcloud_mcp_server.migrations import (
+    create_migration,
+    downgrade_database,
+    get_current_revision,
+    show_migration_history,
+    upgrade_database,
+)
 from nextcloud_mcp_server.observability import get_uvicorn_logging_config
 
 from .app import get_app
@@ -289,8 +296,6 @@ def upgrade(database_path: str, revision: str):
       # 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)
@@ -335,8 +340,6 @@ def downgrade(database_path: str, revision: str):
       # 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)
@@ -362,8 +365,6 @@ def current(database_path: str):
     Example:
       $ nextcloud-mcp-server db current
     """
-    from nextcloud_mcp_server.migrations import get_current_revision
-
     try:
         revision = get_current_revision(database_path)
         if revision:
@@ -397,8 +398,6 @@ def history(database_path: str):
     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)
@@ -421,8 +420,6 @@ def migrate(message: str):
 
     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)

nextcloud_mcp_server/client/__init__.py

@@ -4,7 +4,6 @@ import os
 from httpx import (
     AsyncBaseTransport,
     AsyncClient,
-    AsyncHTTPTransport,
     Auth,
     BasicAuth,
     Request,
@@ -13,6 +12,7 @@ from httpx import (
 )
 
 from ..controllers.notes_search import NotesSearchController
+from ..http import nextcloud_httpx_transport
 from .calendar import CalendarClient
 from .contacts import ContactsClient
 from .cookbook import CookbookClient
@@ -67,7 +67,7 @@ class NextcloudClient:
         self._client = AsyncClient(
             base_url=base_url,
             auth=auth,
-            transport=AsyncDisableCookieTransport(AsyncHTTPTransport()),
+            transport=AsyncDisableCookieTransport(nextcloud_httpx_transport()),
             event_hooks={"request": [log_request], "response": [log_response]},
             timeout=Timeout(timeout=30, connect=5),
         )
@@ -113,7 +113,7 @@ class NextcloudClient:
         Returns:
             NextcloudClient configured with bearer token authentication
         """
-        from ..auth import BearerAuth
+        from ..auth import BearerAuth  # noqa: PLC0415
 
         logger.info(f"Creating NC Client for user '{username}' using OAuth token")
         return cls(base_url=base_url, username=username, auth=BearerAuth(token))

nextcloud_mcp_server/client/calendar.py

@@ -6,12 +6,16 @@ import uuid
 from typing import Any, Dict, List, Optional
 
 import anyio
-from caldav.async_collection import AsyncCalendar
+from caldav.async_collection import AsyncCalendar, AsyncEvent
 from caldav.async_davclient import AsyncDAVClient
+from caldav.elements import cdav, dav
 from httpx import Auth
-from icalendar import Alarm, Calendar, vRecur
+from icalendar import Alarm, Calendar, vDDDTypes, vRecur
 from icalendar import Event as ICalEvent
 from icalendar import Todo as ICalTodo
+from lxml import etree  # type: ignore[import-untyped]
+
+from ..config import get_nextcloud_ssl_verify
 
 logger = logging.getLogger(__name__)
 
@@ -34,6 +38,7 @@ class CalendarClient:
             url=f"{base_url}/remote.php/dav/",
             username=username,
             auth=auth,
+            ssl_verify_cert=get_nextcloud_ssl_verify(),  # type: ignore[arg-type]  # caldav types say bool|str but passes through to httpx which accepts SSLContext
         )
         self._calendar_home_url = f"{base_url}/remote.php/dav/calendars/{username}/"
 
@@ -100,8 +105,6 @@ class CalendarClient:
         # Use custom PROPFIND with CalendarServer namespace (cs:) for calendar-color.
         # caldav library's nsmap lacks "CS" namespace, and its CalendarColor uses
         # Apple iCal namespace which Nextcloud doesn't recognize.
-        from lxml import etree  # type: ignore[import-untyped]
-
         propfind_body = """<?xml version="1.0" encoding="utf-8"?>
 <d:propfind xmlns:d="DAV:" xmlns:cs="http://calendarserver.org/ns/" xmlns:c="urn:ietf:params:xml:ns:caldav">
     <d:prop>
@@ -255,18 +258,35 @@ class CalendarClient:
         """List events in a calendar within date range."""
         calendar = self._get_calendar(calendar_name)
 
-        # Get all events using caldav library (now with proper filter)
-        events = await calendar.events()
+        if start_datetime or end_datetime:
+            # Build CalDAV REPORT with time-range filter for server-side filtering
+            events = await self._search_events_by_date(
+                calendar, start_datetime, end_datetime
+            )
+            # Expand is only used when both bounds are provided
+            expanded = bool(start_datetime and end_datetime)
+        else:
+            # No date filter — fetch all events
+            events = await calendar.events()
+            expanded = False
 
         result = []
         for event in events:
             await event.load(only_if_unloaded=True)
             if event.data:
-                event_dict = self._parse_ical_event(event.data)
-                if event_dict:
-                    event_dict["href"] = str(event.url)
-                    event_dict["etag"] = ""
-                    result.append(event_dict)
+                if expanded:
+                    # Server-side expansion: each response resource may contain
+                    # multiple VEVENTs (one per recurrence occurrence)
+                    for event_dict in self._parse_all_ical_events(event.data):
+                        event_dict["href"] = str(event.url)
+                        event_dict["etag"] = ""
+                        result.append(event_dict)
+                else:
+                    event_dict = self._parse_ical_event(event.data)
+                    if event_dict:
+                        event_dict["href"] = str(event.url)
+                        event_dict["etag"] = ""
+                        result.append(event_dict)
 
             if len(result) >= limit:
                 break
@@ -274,6 +294,53 @@ class CalendarClient:
         logger.debug(f"Found {len(result)} events")
         return result
 
+    async def _search_events_by_date(
+        self,
+        calendar: AsyncCalendar,
+        start_datetime: Optional[dt.datetime] = None,
+        end_datetime: Optional[dt.datetime] = None,
+    ) -> list:
+        """Execute a CalDAV REPORT with time-range filter."""
+        # Ensure naive datetimes are treated as UTC
+        if start_datetime and start_datetime.tzinfo is None:
+            start_datetime = start_datetime.replace(tzinfo=dt.UTC)
+        if end_datetime and end_datetime.tzinfo is None:
+            end_datetime = end_datetime.replace(tzinfo=dt.UTC)
+
+        # Build comp-filter with time-range (mirrors sync Calendar.build_search_xml_query)
+        inner_comp_filter = cdav.CompFilter(name="VEVENT")
+        inner_comp_filter += cdav.TimeRange(start_datetime, end_datetime)
+        outer_comp_filter = cdav.CompFilter(name="VCALENDAR") + inner_comp_filter
+        filter_element = cdav.Filter() + outer_comp_filter
+
+        # When both bounds are provided, request server-side expansion of
+        # recurring events (RFC 4791 §9.6.5). Each occurrence is returned as
+        # a separate VEVENT with its own DTSTART, with RRULE stripped.
+        data = cdav.CalendarData()
+        if start_datetime and end_datetime:
+            data += cdav.Expand(start_datetime, end_datetime)
+
+        query = cdav.CalendarQuery() + [dav.Prop() + data] + filter_element
+
+        body = etree.tostring(
+            query.xmlelement(), encoding="utf-8", xml_declaration=True
+        )
+        assert calendar.client is not None
+        response = await calendar.client.report(str(calendar.url), body, depth=1)
+
+        # Parse response (same pattern as AsyncCalendar.search)
+        objects = []
+        response_data = response.expand_simple_props([cdav.CalendarData()])
+        for href, props in response_data.items():
+            if href == str(calendar.url):
+                continue
+            cal_data = props.get(cdav.CalendarData.tag)
+            if cal_data:
+                obj = AsyncEvent(client=calendar.client, data=cal_data, parent=calendar)
+                objects.append(obj)
+
+        return objects
+
     async def create_event(
         self, calendar_name: str, event_data: Dict[str, Any]
     ) -> Dict[str, Any]:
@@ -583,7 +650,7 @@ class CalendarClient:
         # Add categories
         categories = event_data.get("categories", "")
         if categories:
-            event.add("categories", categories.split(","))
+            event.add("categories", [c.strip() for c in categories.split(",")])
 
         # Add priority and status
         priority = event_data.get("priority", 5)
@@ -633,75 +700,92 @@ class CalendarClient:
         cal.add_component(event)
         return cal.to_ical().decode("utf-8")
 
+    def _extract_vevent_data(self, component) -> Dict[str, Any]:
+        """Extract event data from a single VEVENT component.
+
+        Shared helper used by both _parse_ical_event() and _parse_all_ical_events().
+        """
+        event_data: Dict[str, Any] = {
+            "uid": str(component.get("uid", "")),
+            "title": str(component.get("summary", "")),
+            "description": str(component.get("description", "")),
+            "location": str(component.get("location", "")),
+            "status": str(component.get("status", "CONFIRMED")),
+            "priority": int(component.get("priority", 5)),
+            "privacy": str(component.get("class", "PUBLIC")),
+            "url": str(component.get("url", "")),
+        }
+
+        # Handle dates
+        dtstart = component.get("dtstart")
+        if dtstart:
+            if isinstance(dtstart.dt, dt.date) and not isinstance(
+                dtstart.dt, dt.datetime
+            ):
+                event_data["start_datetime"] = dtstart.dt.isoformat()
+                event_data["all_day"] = True
+            else:
+                event_data["start_datetime"] = dtstart.dt.isoformat()
+                event_data["all_day"] = False
+
+        dtend = component.get("dtend")
+        if dtend:
+            if isinstance(dtend.dt, dt.date) and not isinstance(dtend.dt, dt.datetime):
+                event_data["end_datetime"] = dtend.dt.isoformat()
+            else:
+                event_data["end_datetime"] = dtend.dt.isoformat()
+
+        # Handle categories
+        categories = component.get("categories")
+        if categories:
+            event_data["categories"] = self._extract_categories(categories)
+
+        # Handle recurrence
+        rrule = component.get("rrule")
+        if rrule:
+            event_data["recurring"] = True
+            event_data["recurrence_rule"] = str(rrule)
+
+        # Handle attendees
+        attendees = []
+        for attendee in component.get("attendee", []):
+            if isinstance(attendee, list):
+                attendees.extend(str(a).replace("mailto:", "") for a in attendee)
+            else:
+                attendees.append(str(attendee).replace("mailto:", ""))
+        if attendees:
+            event_data["attendees"] = ",".join(attendees)
+
+        return event_data
+
     def _parse_ical_event(self, ical_text: str) -> Optional[Dict[str, Any]]:
-        """Parse iCalendar text and extract event data."""
+        """Parse iCalendar text and extract the first event."""
         try:
             cal = Calendar.from_ical(ical_text)
             for component in cal.walk():
                 if component.name == "VEVENT":
-                    event_data = {
-                        "uid": str(component.get("uid", "")),
-                        "title": str(component.get("summary", "")),
-                        "description": str(component.get("description", "")),
-                        "location": str(component.get("location", "")),
-                        "status": str(component.get("status", "CONFIRMED")),
-                        "priority": int(component.get("priority", 5)),
-                        "privacy": str(component.get("class", "PUBLIC")),
-                        "url": str(component.get("url", "")),
-                    }
-
-                    # Handle dates
-                    dtstart = component.get("dtstart")
-                    if dtstart:
-                        if isinstance(dtstart.dt, dt.date) and not isinstance(
-                            dtstart.dt, dt.datetime
-                        ):
-                            event_data["start_datetime"] = dtstart.dt.isoformat()
-                            event_data["all_day"] = True
-                        else:
-                            event_data["start_datetime"] = dtstart.dt.isoformat()
-                            event_data["all_day"] = False
-
-                    dtend = component.get("dtend")
-                    if dtend:
-                        if isinstance(dtend.dt, dt.date) and not isinstance(
-                            dtend.dt, dt.datetime
-                        ):
-                            event_data["end_datetime"] = dtend.dt.isoformat()
-                        else:
-                            event_data["end_datetime"] = dtend.dt.isoformat()
-
-                    # Handle categories
-                    categories = component.get("categories")
-                    if categories:
-                        event_data["categories"] = self._extract_categories(categories)
-
-                    # Handle recurrence
-                    rrule = component.get("rrule")
-                    if rrule:
-                        event_data["recurring"] = True
-                        event_data["recurrence_rule"] = str(rrule)
-
-                    # Handle attendees
-                    attendees = []
-                    for attendee in component.get("attendee", []):
-                        if isinstance(attendee, list):
-                            attendees.extend(
-                                str(a).replace("mailto:", "") for a in attendee
-                            )
-                        else:
-                            attendees.append(str(attendee).replace("mailto:", ""))
-                    if attendees:
-                        event_data["attendees"] = ",".join(attendees)
-
-                    return event_data
-
+                    return self._extract_vevent_data(component)
             return None
-
         except Exception as e:
             logger.error(f"Error parsing iCalendar event: {e}")
             return None
 
+    def _parse_all_ical_events(self, ical_text: str) -> list[Dict[str, Any]]:
+        """Parse iCalendar text and extract ALL event occurrences.
+
+        Used with server-side expansion where a single VCALENDAR contains
+        multiple VEVENT components (one per recurrence occurrence).
+        """
+        results: list[Dict[str, Any]] = []
+        try:
+            cal = Calendar.from_ical(ical_text)
+            for component in cal.walk():
+                if component.name == "VEVENT":
+                    results.append(self._extract_vevent_data(component))
+        except Exception as e:
+            logger.error(f"Error parsing iCalendar events: {e}")
+        return results
+
     def _merge_ical_properties(
         self, raw_ical: str, event_data: Dict[str, Any], event_uid: str
     ) -> str:
@@ -727,6 +811,50 @@ class CalendarClient:
                     if "url" in event_data:
                         component["URL"] = event_data["url"]
 
+                    # Handle categories
+                    if "categories" in event_data:
+                        categories_str = event_data["categories"]
+                        if categories_str:
+                            component["CATEGORIES"] = [
+                                c.strip() for c in categories_str.split(",")
+                            ]
+                        elif "CATEGORIES" in component:
+                            del component["CATEGORIES"]
+
+                    # Handle recurrence rule
+                    if "recurrence_rule" in event_data:
+                        rrule_str = event_data["recurrence_rule"]
+                        if rrule_str:
+                            component["RRULE"] = vRecur.from_ical(rrule_str)
+                        elif "RRULE" in component:
+                            del component["RRULE"]
+
+                    # Handle attendees
+                    if "attendees" in event_data:
+                        attendees_str = event_data["attendees"]
+                        # Remove all existing attendees first
+                        while "ATTENDEE" in component:
+                            del component["ATTENDEE"]
+                        if attendees_str:
+                            for email in attendees_str.split(","):
+                                if email.strip():
+                                    component.add("attendee", f"mailto:{email.strip()}")
+
+                    # Handle reminder (VALARM)
+                    if "reminder_minutes" in event_data:
+                        component.subcomponents = [
+                            sub
+                            for sub in component.subcomponents
+                            if sub.name != "VALARM"
+                        ]
+                        minutes = event_data["reminder_minutes"]
+                        if minutes > 0:
+                            alarm = Alarm()
+                            alarm.add("action", "DISPLAY")
+                            alarm.add("description", "Event reminder")
+                            alarm.add("trigger", dt.timedelta(minutes=-minutes))
+                            component.add_component(alarm)
+
                     # Handle dates
                     if "start_datetime" in event_data:
                         start_str = event_data["start_datetime"]
@@ -757,8 +885,6 @@ class CalendarClient:
                             component["DTEND"] = end_dt
 
                     # Update timestamps
-                    from icalendar import vDDDTypes
-
                     now = dt.datetime.now(dt.UTC)
                     component["LAST-MODIFIED"] = vDDDTypes(now)
                     component["DTSTAMP"] = vDDDTypes(now)
@@ -823,24 +949,18 @@ class CalendarClient:
         # Due date
         due = todo_data.get("due", "")
         if due:
-            from icalendar import vDDDTypes
-
             due_dt = self._ensure_timezone_aware(due)
             todo.add("due", vDDDTypes(due_dt))
 
         # Start date
         dtstart = todo_data.get("dtstart", "")
         if dtstart:
-            from icalendar import vDDDTypes
-
             start_dt = self._ensure_timezone_aware(dtstart)
             todo.add("dtstart", vDDDTypes(start_dt))
 
         # Completed timestamp
         completed = todo_data.get("completed", "")
         if completed:
-            from icalendar import vDDDTypes
-
             completed_dt = self._ensure_timezone_aware(completed)
             todo.add("completed", vDDDTypes(completed_dt))
 
@@ -929,9 +1049,6 @@ class CalendarClient:
                         component["PERCENT-COMPLETE"] = percent_value
                         logger.debug(f"Set PERCENT-COMPLETE to {percent_value}")
 
-                    # Import vDDDTypes at the beginning for datetime formatting
-                    from icalendar import vDDDTypes
-
                     # Handle due date
                     if "due" in todo_data:
                         due_str = todo_data["due"]
@@ -960,7 +1077,9 @@ class CalendarClient:
                     if "categories" in todo_data:
                         categories_str = todo_data["categories"]
                         if categories_str:
-                            component["CATEGORIES"] = categories_str.split(",")
+                            component["CATEGORIES"] = [
+                                c.strip() for c in categories_str.split(",")
+                            ]
                             logger.debug(f"Set CATEGORIES to {categories_str}")
 
                     # Update timestamps

nextcloud_mcp_server/client/cookbook.py

@@ -2,6 +2,7 @@
 
 import logging
 from typing import Any, Dict, List
+from urllib.parse import quote
 
 from httpx import Timeout
 
@@ -164,9 +165,6 @@ class CookbookClient(BaseNextcloudClient):
         Returns:
             List of matching recipe stubs
         """
-        # URL encode the query
-        from urllib.parse import quote
-
         encoded_query = quote(query)
         response = await self._make_request(
             "GET", f"/apps/cookbook/api/v1/search/{encoded_query}"
@@ -193,8 +191,6 @@ class CookbookClient(BaseNextcloudClient):
         Returns:
             List of recipe stubs in the category
         """
-        from urllib.parse import quote
-
         encoded_category = quote(category)
         response = await self._make_request(
             "GET", f"/apps/cookbook/api/v1/category/{encoded_category}"
@@ -211,8 +207,6 @@ class CookbookClient(BaseNextcloudClient):
         Returns:
             New category name
         """
-        from urllib.parse import quote
-
         encoded_old_name = quote(old_name)
         response = await self._make_request(
             "PUT",
@@ -241,8 +235,6 @@ class CookbookClient(BaseNextcloudClient):
         Returns:
             List of recipe stubs matching the keywords
         """
-        from urllib.parse import quote
-
         # Join keywords with commas
         keywords_str = ",".join(keywords)
         encoded_keywords = quote(keywords_str)

nextcloud_mcp_server/client/deck.py

@@ -285,28 +285,23 @@ class DeckClient(BaseNextcloudClient):
         archived: Optional[bool] = None,
         done: Optional[str] = None,
     ) -> None:
-        # First, get the current card to use existing values for required fields
+        # Deck PUT API is a full replacement - all required fields must be sent.
+        # Fetch current card to preserve values for fields not being updated.
         current_card = await self.get_card(board_id, stack_id, card_id)
 
-        json_data = {}
-        if title is not None:
-            json_data["title"] = title
-        if description is not None:
-            json_data["description"] = description
-        # Type is required by the API, use provided or keep current
-        json_data["type"] = type if type is not None else current_card.type
-        # Owner is required by the API, use provided or keep current
-        json_data["owner"] = (
-            owner
-            if owner is not None
-            else (
-                current_card.owner
-                if isinstance(current_card.owner, str)
-                else current_card.owner.uid
-                if hasattr(current_card.owner, "uid")
-                else current_card.owner.primaryKey
-            )
-        )
+        # Build payload with required fields always included
+        json_data = {
+            # Title is required by the API
+            "title": title if title is not None else current_card.title,
+            # Type is required by the API
+            "type": type if type is not None else current_card.type,
+            # Owner is required by the API (model validator ensures it's a string)
+            "owner": owner if owner is not None else current_card.owner,
+            # Description must be sent to preserve it (PUT clears omitted fields)
+            "description": description
+            if description is not None
+            else (current_card.description or ""),
+        }
         if order is not None:
             json_data["order"] = order
         if duedate is not None:
@@ -391,11 +386,17 @@ class DeckClient(BaseNextcloudClient):
         order: int,
         target_stack_id: int,
     ) -> None:
+        # Use the non-API route /cards/{cardId}/reorder which correctly reads
+        # stackId from the body. The API route /api/.../stacks/{stackId}/cards/...
+        # has a parameter conflict where URL stackId overrides body stackId.
+        # See: https://github.com/cbcoutinho/nextcloud-mcp-server/issues/469
         json_data = {"order": order, "stackId": target_stack_id}
+        headers = self._get_deck_headers()
         await self._make_request(
             "PUT",
-            f"/apps/deck/api/v1.0/boards/{board_id}/stacks/{stack_id}/cards/{card_id}/reorder",
+            f"/apps/deck/cards/{card_id}/reorder",
             json=json_data,
+            headers=headers,
         )
 
     # Labels

nextcloud_mcp_server/client/notes.py

@@ -4,6 +4,7 @@ import logging
 from typing import Any, AsyncIterator, Dict, Optional
 
 from .base import BaseNextcloudClient
+from .webdav import WebDAVClient
 
 logger = logging.getLogger(__name__)
 
@@ -157,9 +158,6 @@ class NotesClient(BaseNextcloudClient):
                 f"Category changed from '{old_note.get('category', '')}' to '{category}' - cleaning up old attachment directory"
             )
             try:
-                # Import here to avoid circular imports
-                from .webdav import WebDAVClient
-
                 webdav_client = WebDAVClient(self._client, self.username)
                 await webdav_client.cleanup_old_attachment_directory(
                     note_id=note_id, old_category=old_note.get("category", "")
@@ -204,8 +202,6 @@ class NotesClient(BaseNextcloudClient):
 
         # Clean up attachment directories
         try:
-            from .webdav import WebDAVClient
-
             webdav_client = WebDAVClient(self._client, self.username)
 
             for cat in potential_categories:

nextcloud_mcp_server/client/webdav.py

@@ -3,7 +3,9 @@
 import logging
 import mimetypes
 import xml.etree.ElementTree as ET
+from email.utils import parsedate_to_datetime
 from typing import Any, Dict, List, Optional, Tuple
+from urllib.parse import unquote
 
 from httpx import HTTPStatusError
 
@@ -1259,8 +1261,6 @@ class WebDAVClient(BaseNextcloudClient):
                 continue
 
             # Decode href path and extract the file path
-            from urllib.parse import unquote
-
             href_path = unquote(href_elem.text)
             # Remove WebDAV prefix to get user-relative path
             webdav_prefix = f"/remote.php/dav/files/{self.username}/"
@@ -1269,8 +1269,6 @@ class WebDAVClient(BaseNextcloudClient):
             # Parse last modified timestamp
             last_modified_timestamp = None
             if lastmodified_elem is not None and lastmodified_elem.text:
-                from email.utils import parsedate_to_datetime
-
                 try:
                     dt = parsedate_to_datetime(lastmodified_elem.text)
                     last_modified_timestamp = int(dt.timestamp())

nextcloud_mcp_server/config.py

@@ -1,6 +1,8 @@
 import logging
 import logging.config
 import os
+import socket
+import ssl
 from dataclasses import dataclass
 from enum import Enum
 from typing import Any, Optional
@@ -163,6 +165,12 @@ 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
@@ -174,6 +182,10 @@ class Settings:
     nextcloud_username: Optional[str] = None
     nextcloud_password: Optional[str] = None
 
+    # Nextcloud SSL/TLS settings
+    nextcloud_verify_ssl: bool = True
+    nextcloud_ca_bundle: Optional[str] = None
+
     # ADR-005: Token Audience Validation (required for OAuth mode)
     nextcloud_mcp_server_url: Optional[str] = None  # MCP server URL (used as audience)
     nextcloud_resource_uri: Optional[str] = None  # Nextcloud resource identifier
@@ -245,9 +257,23 @@ class Settings:
     log_include_trace_context: bool = True
 
     def __post_init__(self):
-        """Validate Qdrant configuration and set defaults."""
+        """Validate configuration and set defaults."""
         logger = logging.getLogger(__name__)
 
+        # Validate SSL/TLS configuration
+        if not self.nextcloud_verify_ssl:
+            logger.warning(
+                "NEXTCLOUD_VERIFY_SSL is disabled. "
+                "TLS certificate verification is turned off for all Nextcloud connections. "
+                "This is insecure and should only be used for development/testing."
+            )
+        if self.nextcloud_ca_bundle:
+            if not os.path.isfile(self.nextcloud_ca_bundle):
+                raise ValueError(
+                    f"NEXTCLOUD_CA_BUNDLE path does not exist: {self.nextcloud_ca_bundle}"
+                )
+            logger.info("Using custom CA bundle: %s", self.nextcloud_ca_bundle)
+
         # Ensure mutual exclusivity
         if self.qdrant_url and self.qdrant_location:
             raise ValueError(
@@ -331,7 +357,6 @@ class Settings:
         Returns:
             Collection name string
         """
-        import socket
 
         # Use explicit override if user configured non-default value
         if self.qdrant_collection != "nextcloud_content":
@@ -350,6 +375,131 @@ class Settings:
 
         return f"{deployment_id}-{model_name}"
 
+    # ADR-021: Property aliases for new naming convention
+    # These provide the new names while maintaining backward compatibility with old field names
+
+    @property
+    def enable_semantic_search(self) -> bool:
+        """Semantic search enabled (ADR-021 alias for vector_sync_enabled)."""
+        return self.vector_sync_enabled
+
+    @property
+    def enable_background_operations(self) -> bool:
+        """Background operations enabled (ADR-021 alias for enable_offline_access)."""
+        return self.enable_offline_access
+
+
+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.
@@ -357,7 +507,13 @@ def get_settings() -> Settings:
     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"),
@@ -367,6 +523,11 @@ def get_settings() -> Settings:
         nextcloud_host=os.getenv("NEXTCLOUD_HOST"),
         nextcloud_username=os.getenv("NEXTCLOUD_USERNAME"),
         nextcloud_password=os.getenv("NEXTCLOUD_PASSWORD"),
+        # Nextcloud SSL/TLS settings
+        nextcloud_verify_ssl=(
+            os.getenv("NEXTCLOUD_VERIFY_SSL", "true").lower() == "true"
+        ),
+        nextcloud_ca_bundle=os.getenv("NEXTCLOUD_CA_BUNDLE"),
         # ADR-005: Token Audience Validation
         nextcloud_mcp_server_url=os.getenv("NEXTCLOUD_MCP_SERVER_URL"),
         nextcloud_resource_uri=os.getenv("NEXTCLOUD_RESOURCE_URI"),
@@ -378,9 +539,7 @@ def get_settings() -> Settings:
         enable_token_exchange=(
             os.getenv("ENABLE_TOKEN_EXCHANGE", "false").lower() == "true"
         ),
-        enable_offline_access=(
-            os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() == "true"
-        ),
+        enable_offline_access=enable_background_operations,  # Smart dependency resolution
         # Multi-user BasicAuth pass-through mode
         enable_multi_user_basic_auth=(
             os.getenv("ENABLE_MULTI_USER_BASIC_AUTH", "false").lower() == "true"
@@ -391,9 +550,7 @@ 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=(
-            os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
-        ),
+        vector_sync_enabled=enable_semantic_search,  # Smart dependency resolution
         vector_sync_scan_interval=int(os.getenv("VECTOR_SYNC_SCAN_INTERVAL", "300")),
         vector_sync_processor_workers=int(
             os.getenv("VECTOR_SYNC_PROCESSOR_WORKERS", "3")
@@ -436,3 +593,20 @@ def get_settings() -> Settings:
         log_include_trace_context=os.getenv("LOG_INCLUDE_TRACE_CONTEXT", "true").lower()
         == "true",
     )
+
+
+def get_nextcloud_ssl_verify() -> bool | ssl.SSLContext:
+    """Return the SSL verification setting for Nextcloud connections.
+
+    Returns:
+        - False if NEXTCLOUD_VERIFY_SSL=false (disable verification)
+        - ssl.SSLContext if NEXTCLOUD_CA_BUNDLE is set (custom CA)
+        - True otherwise (default system CA verification)
+    """
+    settings = get_settings()
+    if not settings.nextcloud_verify_ssl:
+        return False
+    if settings.nextcloud_ca_bundle:
+        ctx = ssl.create_default_context(cafile=settings.nextcloud_ca_bundle)
+        return ctx
+    return True

nextcloud_mcp_server/config_validators.py

@@ -9,6 +9,7 @@ See ADR-020 for detailed architecture and deployment mode documentation.
 """
 
 import logging
+import os
 from dataclasses import dataclass
 from enum import Enum
 
@@ -105,15 +106,13 @@ MODE_REQUIREMENTS: dict[AuthMode, ModeRequirements] = {
         ],
         conditional={
             "enable_offline_access": [
-                "oidc_client_id",
-                "oidc_client_secret",
+                # OAuth credentials validated separately (lines 397-406) with clearer error message
                 "token_encryption_key",
                 "token_storage_db",
             ],
-            "vector_sync_enabled": [
-                # Requires offline access for background sync
-                "enable_offline_access",
-            ],
+            # 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. "
@@ -152,9 +151,9 @@ MODE_REQUIREMENTS: dict[AuthMode, ModeRequirements] = {
                 "token_encryption_key",
                 "token_storage_db",
             ],
-            "vector_sync_enabled": [
-                "enable_offline_access",  # Background sync requires refresh tokens
-            ],
+            # 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). "
@@ -192,9 +191,9 @@ MODE_REQUIREMENTS: dict[AuthMode, ModeRequirements] = {
                 "token_encryption_key",
                 "token_storage_db",
             ],
-            "vector_sync_enabled": [
-                "enable_offline_access",
-            ],
+            # 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. "
@@ -225,7 +224,8 @@ MODE_REQUIREMENTS: dict[AuthMode, ModeRequirements] = {
 def detect_auth_mode(settings: Settings) -> AuthMode:
     """Detect authentication mode from configuration.
 
-    Mode detection priority (most specific to most general):
+    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
@@ -237,12 +237,41 @@ def detect_auth_mode(settings: Settings) -> AuthMode:
 
     Returns:
         Detected AuthMode
+
+    Raises:
+        ValueError: If explicit deployment_mode is invalid or conflicts with detected mode
     """
+
+    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
-    import os
-
     if os.getenv("SMITHERY_DEPLOYMENT", "false").lower() == "true":
         return AuthMode.SMITHERY_STATELESS
 
@@ -364,22 +393,20 @@ def validate_configuration(settings: Settings) -> tuple[AuthMode, list[str]]:
             )
 
     if mode == AuthMode.MULTI_USER_BASIC:
-        # Validate that if offline access enabled, we have OAuth credentials
+        # 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:
-                errors.append(
-                    f"[{mode.value}] NEXTCLOUD_OIDC_CLIENT_ID and "
-                    "NEXTCLOUD_OIDC_CLIENT_SECRET are required when "
-                    "ENABLE_OFFLINE_ACCESS is enabled (for app password retrieval)"
+                logger.info(
+                    f"[{mode.value}] OAuth credentials not configured. "
+                    "Will attempt Dynamic Client Registration (DCR) at startup "
+                    "(required for app password retrieval via Astrolabe)."
                 )
 
-        # Validate vector sync requirements
-        if settings.vector_sync_enabled and not settings.enable_offline_access:
-            errors.append(
-                f"[{mode.value}] ENABLE_OFFLINE_ACCESS must be enabled when "
-                "VECTOR_SYNC_ENABLED is true (background sync requires "
-                "app passwords or refresh tokens)"
-            )
+        # 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

nextcloud_mcp_server/context.py

@@ -5,6 +5,10 @@ import logging
 from httpx import BasicAuth
 from mcp.server.fastmcp import Context
 
+from nextcloud_mcp_server.auth.context_helper import (
+    get_client_from_context,
+    get_session_client_from_context,
+)
 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import (
     DeploymentMode,
@@ -80,11 +84,6 @@ async def get_client(ctx: Context) -> NextcloudClient:
 
     # OAuth mode (has 'nextcloud_host' attribute)
     if hasattr(lifespan_ctx, "nextcloud_host"):
-        from nextcloud_mcp_server.auth.context_helper import (
-            get_client_from_context,
-            get_session_client_from_context,
-        )
-
         if settings.enable_token_exchange:
             # Mode 2: Exchange MCP token for Nextcloud token
             # Token was validated to have MCP audience in UnifiedTokenVerifier
@@ -131,7 +130,7 @@ def _get_client_from_session_config(ctx: Context) -> NextcloudClient:
         ValueError: If required session config fields are missing
     """
     # ADR-016: Get session config from context variable (set by SmitheryConfigMiddleware)
-    from nextcloud_mcp_server.app import get_smithery_session_config
+    from nextcloud_mcp_server.app import get_smithery_session_config  # noqa: PLC0415
 
     session_config = get_smithery_session_config()
 

nextcloud_mcp_server/document_processors/pymupdf.py

@@ -6,6 +6,8 @@ import tempfile
 from collections.abc import Awaitable, Callable
 from typing import Any, Optional
 
+import anyio
+
 # NOTE: Do NOT call pymupdf.layout.activate() here!
 # It changes the behavior of pymupdf4llm.to_markdown() when page_chunks=True,
 # causing it to return a string instead of a list[dict].
@@ -95,7 +97,6 @@ class PyMuPDFProcessor(DocumentProcessor):
         Raises:
             ProcessorError: If PDF processing fails
         """
-        import anyio
 
         try:
             if progress_callback:

nextcloud_mcp_server/embedding/bm25_provider.py

@@ -3,6 +3,7 @@
 import logging
 from typing import Any
 
+import anyio
 from fastembed import SparseTextEmbedding
 
 logger = logging.getLogger(__name__)
@@ -67,7 +68,6 @@ class BM25SparseEmbeddingProvider:
         Returns:
             Dictionary with 'indices' and 'values' keys for Qdrant sparse vector
         """
-        import anyio
 
         # Run CPU-bound BM25 encoding in thread pool
         return await anyio.to_thread.run_sync(lambda: self.encode(text))  # type: ignore[attr-defined]
@@ -82,7 +82,6 @@ class BM25SparseEmbeddingProvider:
         Returns:
             List of dictionaries with 'indices' and 'values' for each text
         """
-        import anyio
 
         # Run CPU-bound BM25 encoding in thread pool to avoid blocking event loop
         sparse_embeddings = await anyio.to_thread.run_sync(  # type: ignore[attr-defined]

nextcloud_mcp_server/http.py

@@ -0,0 +1,45 @@
+"""Centralized HTTP client factory for Nextcloud connections.
+
+All outbound connections to Nextcloud (API calls, OIDC endpoints) should use
+these factories to ensure consistent SSL/TLS configuration from environment
+variables (NEXTCLOUD_VERIFY_SSL, NEXTCLOUD_CA_BUNDLE).
+"""
+
+from typing import Any
+
+import httpx
+
+from .config import get_nextcloud_ssl_verify
+
+
+def nextcloud_httpx_client(**kwargs: Any) -> httpx.AsyncClient:
+    """Create an httpx.AsyncClient with Nextcloud SSL settings applied.
+
+    Reads NEXTCLOUD_VERIFY_SSL and NEXTCLOUD_CA_BUNDLE from the environment
+    via ``get_nextcloud_ssl_verify()``. Caller-supplied ``verify`` kwarg
+    takes precedence if explicitly provided.
+
+    Args:
+        **kwargs: Forwarded to ``httpx.AsyncClient()``.
+
+    Returns:
+        Configured ``httpx.AsyncClient``.
+    """
+    kwargs.setdefault("verify", get_nextcloud_ssl_verify())
+    return httpx.AsyncClient(**kwargs)
+
+
+def nextcloud_httpx_transport(**kwargs: Any) -> httpx.AsyncHTTPTransport:
+    """Create an httpx.AsyncHTTPTransport with Nextcloud SSL settings applied.
+
+    Used by ``NextcloudClient`` which wraps the transport in
+    ``AsyncDisableCookieTransport``.
+
+    Args:
+        **kwargs: Forwarded to ``httpx.AsyncHTTPTransport()``.
+
+    Returns:
+        Configured ``httpx.AsyncHTTPTransport``.
+    """
+    kwargs.setdefault("verify", get_nextcloud_ssl_verify())
+    return httpx.AsyncHTTPTransport(**kwargs)

nextcloud_mcp_server/migrations.py

@@ -6,10 +6,12 @@ provides CLI integration.
 """
 
 import logging
+import sqlite3
 from pathlib import Path
 
 from alembic.config import Config
 
+import nextcloud_mcp_server.alembic as alembic_package
 from alembic import command
 
 logger = logging.getLogger(__name__)
@@ -29,8 +31,6 @@ def get_alembic_config(database_path: str | Path | None = None) -> Config:
     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")
@@ -98,7 +98,6 @@ def get_current_revision(database_path: str | Path | None = None) -> str | None:
     Returns:
         Current revision ID or None if not versioned
     """
-    import sqlite3
 
     if database_path is None:
         database_path = "/app/data/tokens.db"

nextcloud_mcp_server/models/calendar.py

@@ -34,6 +34,12 @@ class CalendarEventSummary(BaseModel):
     status: Optional[str] = Field(
         None, description="Event status (CONFIRMED, TENTATIVE, CANCELLED)"
     )
+    calendar_name: Optional[str] = Field(
+        None, description="Calendar containing this event"
+    )
+    calendar_display_name: Optional[str] = Field(
+        None, description="Display name of calendar containing this event"
+    )
 
 
 class CalendarEvent(CalendarEventSummary):

nextcloud_mcp_server/models/deck.py

@@ -261,6 +261,20 @@ class CreateLabelResponse(BaseResponse):
     color: str = Field(description="The created label color")
 
 
+class ListCardsResponse(BaseResponse):
+    """Response model for listing deck cards."""
+
+    cards: list[DeckCard] = Field(description="List of deck cards")
+    total: int = Field(description="Total number of cards")
+
+
+class ListLabelsResponse(BaseResponse):
+    """Response model for listing deck labels."""
+
+    labels: list[DeckLabel] = Field(description="List of deck labels")
+    total: int = Field(description="Total number of labels")
+
+
 class LabelOperationResponse(StatusResponse):
     """Response model for label operations like update/delete."""
 

nextcloud_mcp_server/observability/metrics.py

@@ -14,7 +14,9 @@ and resource usage. Metrics are organized by category:
 - External Dependency Health Metrics
 """
 
+import functools
 import logging
+import time
 
 from prometheus_client import (
     Counter,
@@ -23,6 +25,8 @@ from prometheus_client import (
     start_http_server,
 )
 
+from nextcloud_mcp_server.observability.tracing import trace_operation
+
 logger = logging.getLogger(__name__)
 
 # =============================================================================
@@ -423,10 +427,6 @@ def instrument_tool(func):
     Returns:
         Wrapped function with metrics and tracing instrumentation
     """
-    import functools
-    import time
-
-    from nextcloud_mcp_server.observability.tracing import trace_operation
 
     @functools.wraps(func)
     async def wrapper(*args, **kwargs):

nextcloud_mcp_server/search/algorithms.py

@@ -1,9 +1,16 @@
 """Base interfaces and data structures for search algorithms."""
 
+import logging
 from abc import ABC, abstractmethod
 from dataclasses import dataclass
 from typing import Any, Protocol, runtime_checkable
 
+from qdrant_client.models import FieldCondition, Filter, MatchValue
+
+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
+
 
 @runtime_checkable
 class NextcloudClientProtocol(Protocol):
@@ -78,13 +85,6 @@ async def get_indexed_doc_types(user_id: str) -> set[str]:
         >>> if "note" in types:
         ...     # Search notes
     """
-    import logging
-
-    from qdrant_client.models import FieldCondition, Filter, MatchValue
-
-    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
 
     logger = logging.getLogger(__name__)
     settings = get_settings()

nextcloud_mcp_server/search/context.py

@@ -7,7 +7,14 @@ position markers for better visualization and understanding of search results.
 import logging
 from dataclasses import dataclass
 
+import pymupdf
+import pymupdf4llm
+from qdrant_client.models import FieldCondition, Filter, MatchValue
+
 from nextcloud_mcp_server.client import NextcloudClient
+from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.vector.html_processor import html_to_markdown
+from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
 
 logger = logging.getLogger(__name__)
 
@@ -31,11 +38,6 @@ async def _get_chunk_from_qdrant(
         Full chunk text from Qdrant excerpt field, 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()
 
@@ -101,11 +103,6 @@ async def _get_chunk_by_index_from_qdrant(
         Full chunk text from Qdrant excerpt field, 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()
 
@@ -162,11 +159,6 @@ async def _get_file_path_from_qdrant(
         File path string, or None if not found in Qdrant
     """
     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()
 
@@ -222,11 +214,6 @@ async def _get_deck_metadata_from_qdrant(
         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()
 
@@ -352,8 +339,6 @@ async def get_chunk_with_context(
 
             # Fetch adjacent chunks for context expansion
             # Get chunk overlap from config to remove duplicate text
-            from nextcloud_mcp_server.config import get_settings
-
             settings = get_settings()
             chunk_overlap = settings.document_chunk_overlap
 
@@ -549,8 +534,6 @@ async def _fetch_document_text(
                     # Extract text from PDF using PyMuPDF
                     # IMPORTANT: Use pymupdf4llm.to_markdown() to match indexing extraction
                     # This ensures character offsets align between indexed chunks and retrieval
-                    import pymupdf
-                    import pymupdf4llm
 
                     logger.debug(f"Extracting text from PDF: {file_path}")
                     pdf_doc = pymupdf.open(stream=file_content, filetype="pdf")
@@ -586,8 +569,6 @@ async def _fetch_document_text(
                 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

nextcloud_mcp_server/search/pdf_highlighter.py

@@ -10,10 +10,16 @@ varies between indexing and rendering.
 
 import logging
 import re
+import shutil
+import tempfile
+from collections import defaultdict
+from io import BytesIO
+from pathlib import Path
 from typing import Optional
 
 import pymupdf
 import pymupdf4llm
+from PIL import Image, ImageDraw
 
 logger = logging.getLogger(__name__)
 
@@ -77,8 +83,6 @@ class PDFHighlighter:
             Tuple of (full_text, page_boundaries) where page_boundaries is a list of:
             {"page": 1, "start_offset": 0, "end_offset": 1234}
         """
-        import tempfile
-        from pathlib import Path
 
         page_boundaries = []
         text_parts = []
@@ -110,7 +114,6 @@ class PDFHighlighter:
         full_text = "".join(text_parts)
 
         # Clean up temp directory and extracted images
-        import shutil
 
         try:
             shutil.rmtree(temp_dir)
@@ -590,8 +593,6 @@ class PDFHighlighter:
         Returns:
             Tuple of (png_bytes, page_number, highlight_count) or None if failed
         """
-        import tempfile
-        from pathlib import Path
 
         temp_pdf_path = None
         try:
@@ -684,8 +685,6 @@ class PDFHighlighter:
             # Clean up temp directory and PDF file
             if temp_pdf_path and temp_pdf_path.parent.exists():
                 try:
-                    import shutil
-
                     shutil.rmtree(temp_pdf_path.parent)
                 except Exception as e:
                     logger.warning(
@@ -722,11 +721,6 @@ class PDFHighlighter:
             Dict mapping chunk_index to (png_bytes, page_number, highlight_count)
             Chunks that fail to highlight are omitted from the result.
         """
-        import shutil
-        import tempfile
-        from collections import defaultdict
-        from pathlib import Path
-
         results: dict[int, tuple[bytes, int, int]] = {}
 
         if not chunks:
@@ -800,9 +794,6 @@ class PDFHighlighter:
 
             # OPTIMIZATION: Render each page ONCE, then draw highlights using PIL
             # This avoids expensive page.get_pixmap() calls per chunk
-            from io import BytesIO
-
-            from PIL import Image, ImageDraw
 
             # PIL color for bounding box (RGB tuple)
             rgb = PDFHighlighter.COLORS.get(color, PDFHighlighter.COLORS["yellow"])

nextcloud_mcp_server/server/calendar.py

@@ -9,15 +9,46 @@ from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
 from nextcloud_mcp_server.models.calendar import (
     Calendar,
+    CalendarEventSummary,
     ListCalendarsResponse,
+    ListEventsResponse,
     ListTodosResponse,
     Todo,
+    UpcomingEventsResponse,
 )
 from nextcloud_mcp_server.observability.metrics import instrument_tool
 
 logger = logging.getLogger(__name__)
 
 
+def _event_dict_to_summary(event: dict) -> CalendarEventSummary:
+    """Convert a raw event dict from the calendar client to a CalendarEventSummary."""
+    raw_categories = event.get("categories", [])
+    if isinstance(raw_categories, str):
+        categories = [c.strip() for c in raw_categories.split(",") if c.strip()]
+    else:
+        categories = raw_categories
+
+    start = event.get("start_datetime", "")
+    if not start:
+        logger.debug("Event %s has no start_datetime", event.get("uid", "unknown"))
+
+    return CalendarEventSummary(
+        uid=event.get("uid", ""),
+        summary=event.get("title", ""),
+        start=start,
+        end=event.get("end_datetime"),
+        all_day=event.get("all_day", False),
+        location=event.get("location") or None,
+        description=event.get("description") or None,
+        categories=categories,
+        status=event.get("status"),
+        calendar_name=event.get("calendar_name"),
+        calendar_display_name=event.get("calendar_display_name")
+        or event.get("calendar_name"),
+    )
+
+
 def configure_calendar_tools(mcp: FastMCP):
     # Calendar tools
     @mcp.tool(
@@ -204,7 +235,7 @@ def configure_calendar_tools(mcp: FastMCP):
                 end_datetime=end_datetime,
                 filters=filters if filters else None,
             )
-            return events[:limit]
+            events = events[:limit]
         else:
             # Search in specific calendar
             events = await client.calendar.get_calendar_events(
@@ -214,11 +245,25 @@ def configure_calendar_tools(mcp: FastMCP):
                 limit=limit,
             )
 
+            # Enrich events with calendar context for per-event mapping.
+            # Note: calendar_display_name is not available here without an
+            # extra list_calendars() call; the response-level calendar_name
+            # already identifies the calendar for single-calendar queries.
+            for event in events:
+                event["calendar_name"] = calendar_name
+
             # Apply filters if provided
             if filters:
                 events = client.calendar._apply_event_filters(events, filters)
 
-            return events
+        summaries = [_event_dict_to_summary(e) for e in events]
+        return ListEventsResponse(
+            events=summaries,
+            calendar_name=None if search_all_calendars else calendar_name,
+            start_date=start_date or None,
+            end_date=end_date or None,
+            total_found=len(summaries),
+        )
 
     @mcp.tool(
         title="Get Calendar Event",
@@ -420,12 +465,15 @@ def configure_calendar_tools(mcp: FastMCP):
 
         if calendar_name:
             # Get events from specific calendar
-            return await client.calendar.get_calendar_events(
+            events = await client.calendar.get_calendar_events(
                 calendar_name=calendar_name,
                 start_datetime=now,
                 end_datetime=end_datetime,
                 limit=limit,
             )
+            # calendar_display_name not available without extra API call
+            for event in events:
+                event["calendar_name"] = calendar_name
         else:
             # Get events from all calendars
             all_calendars = await client.calendar.list_calendars()
@@ -433,17 +481,16 @@ def configure_calendar_tools(mcp: FastMCP):
 
             for calendar in all_calendars:
                 try:
-                    events = await client.calendar.get_calendar_events(
+                    cal_events = await client.calendar.get_calendar_events(
                         calendar_name=calendar["name"],
                         start_datetime=now,
                         end_datetime=end_datetime,
                         limit=limit,
                     )
-                    # Add calendar info to each event
-                    for event in events:
+                    for event in cal_events:
                         event["calendar_name"] = calendar["name"]
                         event["calendar_display_name"] = calendar["display_name"]
-                    all_events.extend(events)
+                    all_events.extend(cal_events)
                 except Exception as e:
                     logger.warning(
                         f"Error getting events from calendar {calendar['name']}: {e}"
@@ -452,7 +499,14 @@ def configure_calendar_tools(mcp: FastMCP):
 
             # Sort by start time and limit
             all_events.sort(key=lambda x: x.get("start_datetime", ""))
-            return all_events[:limit]
+            events = all_events[:limit]
+
+        summaries = [_event_dict_to_summary(e) for e in events]
+        return UpcomingEventsResponse(
+            events=summaries,
+            days_ahead=days_ahead,
+            calendar_name=calendar_name or None,
+        )
 
     @mcp.tool(
         title="Find Availability",

nextcloud_mcp_server/server/contacts.py

@@ -1,15 +1,57 @@
 import logging
+from typing import Any
 
 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
+from nextcloud_mcp_server.models.contacts import (
+    AddressBook,
+    Contact,
+    ContactField,
+    ListAddressBooksResponse,
+    ListContactsResponse,
+)
 from nextcloud_mcp_server.observability.metrics import instrument_tool
 
 logger = logging.getLogger(__name__)
 
 
+def _raw_contact_to_model(raw: dict) -> Contact:
+    """Convert a raw contact dict from the contacts client to a Contact model.
+
+    Only maps fields the client's list_contacts() currently returns:
+    fullname, nickname, birthday, and email. Additional Contact model fields
+    (phones, addresses, organization, etc.) require expanding the client's
+    vCard parsing in ContactsClient.list_contacts().
+    """
+    contact_info = raw.get("contact", {})
+
+    # Convert email field (str, list, or None) to list[ContactField]
+    raw_email = contact_info.get("email")
+    emails: list[ContactField] = []
+    if isinstance(raw_email, list):
+        emails = [ContactField(type="email", value=e) for e in raw_email if e]
+    elif isinstance(raw_email, str) and raw_email:
+        emails = [ContactField(type="email", value=raw_email)]
+
+    # Nickname goes into custom_fields (no dedicated model field)
+    custom_fields: dict[str, Any] = {}
+    nickname = contact_info.get("nickname")
+    if nickname:
+        custom_fields["nickname"] = nickname
+
+    return Contact(
+        uid=raw["vcard_id"],
+        fn=contact_info.get("fullname", ""),
+        etag=raw.get("getetag"),
+        birthday=contact_info.get("birthday"),
+        emails=emails,
+        custom_fields=custom_fields,
+    )
+
+
 def configure_contacts_tools(mcp: FastMCP):
     # Contacts tools
     @mcp.tool(
@@ -18,10 +60,23 @@ def configure_contacts_tools(mcp: FastMCP):
     )
     @require_scopes("contacts:read")
     @instrument_tool
-    async def nc_contacts_list_addressbooks(ctx: Context):
+    async def nc_contacts_list_addressbooks(ctx: Context) -> ListAddressBooksResponse:
         """List all addressbooks for the user."""
         client = await get_client(ctx)
-        return await client.contacts.list_addressbooks()
+        addressbooks_data = await client.contacts.list_addressbooks()
+        addressbooks = [
+            AddressBook(
+                # ab["name"] is a short slug like "contacts", not a full CardDAV URI;
+                # all tools use it as a path segment: f"{carddav_path}/{name}/"
+                uri=ab["name"],
+                displayname=ab.get("display_name", ab["name"]),
+                ctag=ab.get("getctag"),
+            )
+            for ab in addressbooks_data
+        ]
+        return ListAddressBooksResponse(
+            addressbooks=addressbooks, total_count=len(addressbooks)
+        )
 
     @mcp.tool(
         title="List Contacts",
@@ -29,10 +84,16 @@ def configure_contacts_tools(mcp: FastMCP):
     )
     @require_scopes("contacts:read")
     @instrument_tool
-    async def nc_contacts_list_contacts(ctx: Context, *, addressbook: str):
+    async def nc_contacts_list_contacts(
+        ctx: Context, *, addressbook: str
+    ) -> ListContactsResponse:
         """List all contacts in the specified addressbook."""
         client = await get_client(ctx)
-        return await client.contacts.list_contacts(addressbook=addressbook)
+        contacts_data = await client.contacts.list_contacts(addressbook=addressbook)
+        contacts = [_raw_contact_to_model(c) for c in contacts_data]
+        return ListContactsResponse(
+            contacts=contacts, addressbook=addressbook, total_count=len(contacts)
+        )
 
     @mcp.tool(
         title="Create Address Book",

nextcloud_mcp_server/server/deck.py

@@ -17,6 +17,10 @@ from nextcloud_mcp_server.models.deck import (
     DeckLabel,
     DeckStack,
     LabelOperationResponse,
+    ListBoardsResponse,
+    ListCardsResponse,
+    ListLabelsResponse,
+    ListStacksResponse,
     StackOperationResponse,
 )
 from nextcloud_mcp_server.observability.metrics import instrument_tool
@@ -103,7 +107,7 @@ def configure_deck_tools(mcp: FastMCP):
         )
         client = await get_client(ctx)
         board = await client.deck.get_board(board_id)
-        return [label.model_dump() for label in board.labels]
+        return [label.model_dump() for label in (board.labels or [])]
 
     @mcp.resource("nc://Deck/boards/{board_id}/labels/{label_id}")
     async def deck_label_resource(board_id: int, label_id: int):
@@ -124,11 +128,11 @@ def configure_deck_tools(mcp: FastMCP):
     )
     @require_scopes("deck:read")
     @instrument_tool
-    async def deck_get_boards(ctx: Context) -> list[DeckBoard]:
+    async def deck_get_boards(ctx: Context) -> ListBoardsResponse:
         """Get all Nextcloud Deck boards"""
         client = await get_client(ctx)
         boards = await client.deck.get_boards()
-        return boards
+        return ListBoardsResponse(boards=boards, total=len(boards))
 
     @mcp.tool(
         title="Get Deck Board",
@@ -148,11 +152,11 @@ def configure_deck_tools(mcp: FastMCP):
     )
     @require_scopes("deck:read")
     @instrument_tool
-    async def deck_get_stacks(ctx: Context, board_id: int) -> list[DeckStack]:
+    async def deck_get_stacks(ctx: Context, board_id: int) -> ListStacksResponse:
         """Get all stacks in a Nextcloud Deck board"""
         client = await get_client(ctx)
         stacks = await client.deck.get_stacks(board_id)
-        return stacks
+        return ListStacksResponse(stacks=stacks, total=len(stacks))
 
     @mcp.tool(
         title="Get Deck Stack",
@@ -174,13 +178,12 @@ def configure_deck_tools(mcp: FastMCP):
     @instrument_tool
     async def deck_get_cards(
         ctx: Context, board_id: int, stack_id: int
-    ) -> list[DeckCard]:
+    ) -> ListCardsResponse:
         """Get all cards in a Nextcloud Deck stack"""
         client = await get_client(ctx)
         stack = await client.deck.get_stack(board_id, stack_id)
-        if stack.cards:
-            return stack.cards
-        return []
+        cards = stack.cards or []
+        return ListCardsResponse(cards=cards, total=len(cards))
 
     @mcp.tool(
         title="Get Deck Card",
@@ -202,11 +205,12 @@ def configure_deck_tools(mcp: FastMCP):
     )
     @require_scopes("deck:read")
     @instrument_tool
-    async def deck_get_labels(ctx: Context, board_id: int) -> list[DeckLabel]:
+    async def deck_get_labels(ctx: Context, board_id: int) -> ListLabelsResponse:
         """Get all labels in a Nextcloud Deck board"""
         client = await get_client(ctx)
         board = await client.deck.get_board(board_id)
-        return board.labels
+        labels = board.labels or []
+        return ListLabelsResponse(labels=labels, total=len(labels))
 
     @mcp.tool(
         title="Get Deck Label",
@@ -637,7 +641,9 @@ def configure_deck_tools(mcp: FastMCP):
 
     @mcp.tool(
         title="Remove Label from Deck Card",
-        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
     )
     @require_scopes("deck:write")
     @instrument_tool
@@ -692,7 +698,9 @@ def configure_deck_tools(mcp: FastMCP):
 
     @mcp.tool(
         title="Unassign User from Deck Card",
-        annotations=ToolAnnotations(idempotentHint=False, openWorldHint=True),
+        annotations=ToolAnnotations(
+            destructiveHint=True, idempotentHint=True, openWorldHint=True
+        ),
     )
     @require_scopes("deck:write")
     @instrument_tool

nextcloud_mcp_server/server/oauth_tools.py

@@ -8,10 +8,11 @@ Nextcloud access using the Flow 2 (Resource Provisioning) OAuth flow.
 import logging
 import os
 import secrets
+from datetime import datetime, timezone
 from typing import Optional
 from urllib.parse import urlencode
 
-import httpx
+import jwt
 from mcp.server.auth.middleware.auth_context import get_access_token
 from mcp.server.auth.provider import AccessToken
 from mcp.server.fastmcp import Context
@@ -19,9 +20,13 @@ from mcp.types import ToolAnnotations
 from pydantic import BaseModel, Field
 
 from nextcloud_mcp_server.auth import require_scopes
+from nextcloud_mcp_server.auth.astrolabe_client import AstrolabeClient
 from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
 from nextcloud_mcp_server.auth.userinfo_routes import _query_idp_userinfo
+from nextcloud_mcp_server.config import get_settings
+
+from ..http import nextcloud_httpx_client
 
 logger = logging.getLogger(__name__)
 
@@ -53,8 +58,6 @@ async def extract_user_id_from_token(ctx: Context) -> str:
     # Try JWT decode first
     if is_jwt:
         try:
-            import jwt
-
             payload = jwt.decode(token, options={"verify_signature": False})
             user_id = payload.get("sub", "unknown")
             logger.info(f"  ✓ JWT decode successful: user_id={user_id}")
@@ -70,7 +73,7 @@ async def extract_user_id_from_token(ctx: Context) -> str:
             "OIDC_DISCOVERY_URI",
             "http://localhost:8080/.well-known/openid-configuration",
         )
-        async with httpx.AsyncClient() as http_client:
+        async with nextcloud_httpx_client() as http_client:
             discovery_response = await http_client.get(oidc_discovery_uri)
             discovery_response.raise_for_status()
             discovery = discovery_response.json()
@@ -157,11 +160,6 @@ 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)
@@ -303,16 +301,15 @@ async def provision_nextcloud_access(
                 ),
             )
 
-        # Get configuration
-        enable_offline_access = (
-            os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() == "true"
-        )
-        if not enable_offline_access:
+        # Get configuration using settings (handles both ENABLE_BACKGROUND_OPERATIONS
+        # and ENABLE_OFFLINE_ACCESS environment variables)
+        settings = get_settings()
+        if not settings.enable_offline_access:
             return ProvisioningResult(
                 success=False,
                 message=(
                     "Offline access is not enabled. "
-                    "Set ENABLE_OFFLINE_ACCESS=true to use this feature."
+                    "Set ENABLE_BACKGROUND_OPERATIONS=true to use this feature."
                 ),
             )
 
@@ -488,13 +485,12 @@ async def check_logged_in(ctx: Context, user_id: Optional[str] = None) -> str:
         logger.info("=" * 60)
 
         # Not logged in - generate OAuth URL for Flow 2
-        enable_offline_access = (
-            os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() == "true"
-        )
-        if not enable_offline_access:
+        # Use settings (handles both ENABLE_BACKGROUND_OPERATIONS and ENABLE_OFFLINE_ACCESS)
+        settings = get_settings()
+        if not settings.enable_offline_access:
             return (
                 "Not logged in. Offline access is not enabled. "
-                "Set ENABLE_OFFLINE_ACCESS=true to use this feature."
+                "Set ENABLE_BACKGROUND_OPERATIONS=true to use this feature."
             )
 
         # Get MCP server's OAuth client credentials

nextcloud_mcp_server/server/semantic.py

@@ -7,15 +7,19 @@ from httpx import RequestError
 from mcp.server.fastmcp import Context, FastMCP
 from mcp.shared.exceptions import McpError
 from mcp.types import (
+    ClientCapabilities,
     ErrorData,
     ModelHint,
     ModelPreferences,
+    SamplingCapability,
     SamplingMessage,
     TextContent,
     ToolAnnotations,
 )
+from qdrant_client.models import Filter
 
 from nextcloud_mcp_server.auth import require_scopes
+from nextcloud_mcp_server.config import get_settings
 from nextcloud_mcp_server.context import get_client
 from nextcloud_mcp_server.models.semantic import (
     SamplingSearchResponse,
@@ -28,6 +32,8 @@ from nextcloud_mcp_server.observability.metrics import (
 )
 from nextcloud_mcp_server.search.bm25_hybrid import BM25HybridSearchAlgorithm
 from nextcloud_mcp_server.search.context import get_chunk_with_context
+from nextcloud_mcp_server.vector.placeholder import get_placeholder_filter
+from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
 
 logger = logging.getLogger(__name__)
 
@@ -82,8 +88,6 @@ def configure_semantic_tools(mcp: FastMCP):
         Returns:
             SemanticSearchResponse with matching documents ranked by fusion scores
         """
-        from nextcloud_mcp_server.config import get_settings
-
         settings = get_settings()
         client = await get_client(ctx)
         username = client.username
@@ -373,8 +377,6 @@ def configure_semantic_tools(mcp: FastMCP):
             )
 
         # 3. Check if client supports sampling
-        from mcp.types import ClientCapabilities, SamplingCapability
-
         client_has_sampling = ctx.session.check_client_capability(
             ClientCapabilities(sampling=SamplingCapability())
         )
@@ -656,14 +658,10 @@ def configure_semantic_tools(mcp: FastMCP):
         This is useful for determining when vector indexing is complete
         after creating or updating content across all indexed apps.
         """
-        import os
 
-        # Check if vector sync is enabled
-        vector_sync_enabled = (
-            os.getenv("VECTOR_SYNC_ENABLED", "false").lower() == "true"
-        )
-
-        if not vector_sync_enabled:
+        # Check if vector sync is enabled (supports both old and new env var names)
+        settings = get_settings()
+        if not settings.vector_sync_enabled:
             return VectorSyncStatusResponse(
                 indexed_count=0,
                 pending_count=0,
@@ -696,15 +694,6 @@ 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, excluding placeholders

nextcloud_mcp_server/server/tables.py

@@ -5,6 +5,7 @@ from mcp.types import ToolAnnotations
 
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
+from nextcloud_mcp_server.models.tables import ListTablesResponse, Table
 from nextcloud_mcp_server.observability.metrics import instrument_tool
 
 logger = logging.getLogger(__name__)
@@ -18,10 +19,12 @@ def configure_tables_tools(mcp: FastMCP):
     )
     @require_scopes("tables:read")
     @instrument_tool
-    async def nc_tables_list_tables(ctx: Context):
+    async def nc_tables_list_tables(ctx: Context) -> ListTablesResponse:
         """List all tables available to the user"""
         client = await get_client(ctx)
-        return await client.tables.list_tables()
+        tables_data = await client.tables.list_tables()
+        tables = [Table(**t) for t in tables_data]
+        return ListTablesResponse(tables=tables, total_count=len(tables))
 
     @mcp.tool(
         title="Get Table Schema",

nextcloud_mcp_server/server/webdav.py

@@ -1,3 +1,4 @@
+import base64
 import logging
 
 from mcp.server.fastmcp import Context, FastMCP
@@ -120,7 +121,6 @@ def configure_webdav_tools(mcp: FastMCP):
                 pass
 
         # For binary files, return metadata and base64 encoded content
-        import base64
 
         return {
             "path": path,
@@ -156,8 +156,6 @@ def configure_webdav_tools(mcp: FastMCP):
 
         # Handle base64 encoded content
         if content_type and "base64" in content_type.lower():
-            import base64
-
             content_bytes = base64.b64decode(content)
             content_type = content_type.replace(";base64", "")
         else:

nextcloud_mcp_server/smithery_main.py

@@ -36,7 +36,7 @@ def main():
     logger.info("Starting Nextcloud MCP Server in Smithery stateless mode")
 
     # Import app after setting environment variables
-    from nextcloud_mcp_server.app import get_app
+    from nextcloud_mcp_server.app import get_app  # noqa: PLC0415
 
     # Create the app with streamable-http transport (required for Smithery)
     app = get_app(transport="streamable-http")

nextcloud_mcp_server/vector/document_chunker.py

@@ -3,6 +3,7 @@
 import logging
 from dataclasses import dataclass
 
+import anyio
 from langchain_text_splitters import RecursiveCharacterTextSplitter
 
 logger = logging.getLogger(__name__)
@@ -68,7 +69,6 @@ class DocumentChunker:
         Returns:
             List of chunks with their character positions in the original content
         """
-        import anyio
 
         # Handle empty content - return single empty chunk for backward compatibility
         if not content:

nextcloud_mcp_server/vector/html_processor.py

@@ -1,6 +1,7 @@
 """HTML to Markdown conversion utilities for vector sync."""
 
 import logging
+import re
 
 from markdownify import markdownify as md
 
@@ -43,7 +44,6 @@ def html_to_markdown(html_content: str | None) -> str:
     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

@@ -1,14 +1,23 @@
-"""OAuth mode vector sync orchestration.
+"""Multi-user 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
+Manages background vector sync for multi-user deployments:
+- User Manager: Monitors storage 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)
+Authentication strategies are mutually exclusive by deployment mode:
+
+Multi-user BasicAuth mode (ENABLE_MULTI_USER_BASIC_AUTH=true):
+- Uses app passwords stored locally in MCP server's database
+- Users provision via Astrolabe personal settings, which sends to MCP API
+- OAuth is NOT used
+
+OAuth mode (with external IdP like Keycloak):
+- Uses OAuth refresh tokens via TokenBrokerService
+- Users provision via browser OAuth flow
+- App passwords are NOT used
+
+These are separate concerns - no fallback between them.
 """
 
 import logging
@@ -22,15 +31,15 @@ from anyio.streams.memory import (
     MemoryObjectReceiveStream,
     MemoryObjectSendStream,
 )
-from httpx import BasicAuth
+from httpx import BasicAuth, HTTPStatusError
 
-from nextcloud_mcp_server.auth.astrolabe_client import AstrolabeClient
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.vector.processor import process_document
 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__)
@@ -59,16 +68,59 @@ class UserSyncState:
     started_at: float = field(default_factory=time.time)
 
 
-async def get_user_client(
+async def get_user_client_basic_auth(
+    user_id: str,
+    nextcloud_host: str,
+    storage: "RefreshTokenStorage | None" = None,
+) -> NextcloudClient:
+    """Get an authenticated NextcloudClient using app password (BasicAuth mode).
+
+    For multi-user BasicAuth deployments where users provision app passwords
+    via Astrolabe personal settings. The app password is stored locally in the
+    MCP server's database after being provisioned through the management API.
+
+    Args:
+        user_id: User identifier
+        nextcloud_host: Nextcloud base URL
+        storage: Optional RefreshTokenStorage instance (created from env if not provided)
+
+    Returns:
+        Authenticated NextcloudClient with BasicAuth
+
+    Raises:
+        NotProvisionedError: If user has not provisioned an app password
+    """
+    # Get or create storage instance
+    if storage is None:
+        storage = RefreshTokenStorage.from_env()
+        await storage.initialize()
+
+    # Retrieve app password from local storage
+    app_password = await storage.get_app_password(user_id)
+
+    if not app_password:
+        raise NotProvisionedError(
+            f"User {user_id} has not provisioned an app password. "
+            f"User must configure background sync in Astrolabe personal settings."
+        )
+
+    logger.info(f"Using app password for background sync: {user_id}")
+    return NextcloudClient(
+        base_url=nextcloud_host,
+        username=user_id,
+        auth=BasicAuth(user_id, app_password),
+    )
+
+
+async def get_user_client_oauth(
     user_id: str,
     token_broker: "TokenBrokerService",
     nextcloud_host: str,
 ) -> NextcloudClient:
-    """Get an authenticated NextcloudClient for a user.
+    """Get an authenticated NextcloudClient using OAuth refresh token.
 
-    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)
+    For OAuth deployments with external IdP where users provision via
+    browser OAuth flow. App passwords are NOT used in this mode.
 
     Args:
         user_id: User identifier
@@ -76,45 +128,19 @@ async def get_user_client(
         nextcloud_host: Nextcloud base URL
 
     Returns:
-        Authenticated NextcloudClient
+        Authenticated NextcloudClient with Bearer token
 
     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")
+        raise NotProvisionedError(
+            f"User {user_id} has not provisioned offline access. "
+            f"User must complete the OAuth provisioning flow."
+        )
 
+    logger.info(f"Using OAuth refresh token for background sync: {user_id}")
     return NextcloudClient.from_token(
         base_url=nextcloud_host,
         token=token,
@@ -122,39 +148,109 @@ async def get_user_client(
     )
 
 
+async def get_user_client(
+    user_id: str,
+    token_broker: "TokenBrokerService | None",
+    nextcloud_host: str,
+    *,
+    use_basic_auth: bool = False,
+) -> NextcloudClient:
+    """Get an authenticated NextcloudClient for a user.
+
+    Dispatches to the appropriate authentication strategy based on mode.
+    These are mutually exclusive - no fallback between them.
+
+    Args:
+        user_id: User identifier
+        token_broker: Token broker for OAuth mode (can be None for BasicAuth mode)
+        nextcloud_host: Nextcloud base URL
+        use_basic_auth: If True, use app passwords via Astrolabe (BasicAuth mode).
+                       If False, use OAuth refresh tokens (OAuth mode).
+
+    Returns:
+        Authenticated NextcloudClient
+
+    Raises:
+        NotProvisionedError: If user has not provisioned access for the mode
+    """
+    if use_basic_auth:
+        return await get_user_client_basic_auth(user_id, nextcloud_host)
+    else:
+        if token_broker is None:
+            raise ValueError("token_broker required for OAuth mode")
+        return await get_user_client_oauth(user_id, token_broker, nextcloud_host)
+
+
 async def user_scanner_task(
     user_id: str,
     send_stream: MemoryObjectSendStream[DocumentTask],
     shutdown_event: anyio.Event,
     wake_event: anyio.Event,
-    token_broker: "TokenBrokerService",
+    token_broker: "TokenBrokerService | None",
     nextcloud_host: str,
     *,
+    use_basic_auth: bool = False,
     task_status: TaskStatus = anyio.TASK_STATUS_IGNORED,
 ) -> None:
-    """Scanner task for a single user in OAuth mode.
+    """Scanner task for a single user.
 
-    Gets a fresh token at the start of each scan cycle.
+    Gets fresh credentials 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
+        token_broker: Token broker for OAuth mode (None for BasicAuth mode)
         nextcloud_host: Nextcloud base URL
+        use_basic_auth: If True, use app passwords; if False, use OAuth tokens
         task_status: Status object for signaling task readiness
     """
-    logger.info(f"[OAuth] Scanner started for user: {user_id}")
+    mode_label = "BasicAuth" if use_basic_auth else "OAuth"
+    logger.info(f"[{mode_label}] Scanner started for user: {user_id}")
     settings = get_settings()
+    max_consecutive_errors = 5
 
     task_status.started()
 
+    # Pre-validate credentials before entering scan loop
+    try:
+        nc_client = await get_user_client(
+            user_id, token_broker, nextcloud_host, use_basic_auth=use_basic_auth
+        )
+        try:
+            await nc_client.capabilities()  # Lightweight OCS call to validate creds
+            logger.info(f"[{mode_label}] Credentials validated for {user_id}")
+        except HTTPStatusError as e:
+            if e.response.status_code in (401, 403):
+                logger.warning(
+                    f"[{mode_label}] Credential validation failed for {user_id} "
+                    f"(HTTP {e.response.status_code}), not starting scan loop"
+                )
+                return
+            raise
+        finally:
+            await nc_client.close()
+    except NotProvisionedError:
+        logger.warning(
+            f"[{mode_label}] User {user_id} not provisioned, not starting scan loop"
+        )
+        return
+    except Exception as e:
+        logger.warning(
+            f"[{mode_label}] Pre-validation failed for {user_id}: {e}. "
+            f"Proceeding to scan loop (has its own error handling)."
+        )
+
+    consecutive_errors = 0
+
     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)
+            # Get fresh credentials for this scan cycle
+            nc_client = await get_user_client(
+                user_id, token_broker, nextcloud_host, use_basic_auth=use_basic_auth
+            )
 
             # Scan user's documents
             await scan_user_documents(
@@ -163,19 +259,64 @@ async def user_scanner_task(
                 nc_client=nc_client,
             )
 
+            consecutive_errors = 0  # Reset on success
+
         except NotProvisionedError:
             logger.warning(
-                f"[OAuth] User {user_id} no longer provisioned, stopping scanner"
+                f"[{mode_label}] User {user_id} no longer provisioned, stopping scanner"
             )
             break
 
+        except HTTPStatusError as e:
+            status_code = e.response.status_code
+            if status_code in (401, 403):
+                logger.warning(
+                    f"[{mode_label}] Scanner auth failed for {user_id} "
+                    f"(HTTP {status_code}), stopping scanner. "
+                    f"User may need to re-provision credentials."
+                )
+                break
+            elif status_code == 429:
+                retry_after = min(int(e.response.headers.get("Retry-After", "60")), 300)
+                logger.warning(
+                    f"[{mode_label}] Scanner rate-limited for {user_id}, "
+                    f"backing off {retry_after}s"
+                )
+                try:
+                    with anyio.move_on_after(retry_after):
+                        await shutdown_event.wait()
+                # anyio.get_cancelled_exc_class() catches task cancellation
+                # (e.g. from task group teardown) so we exit cleanly.
+                except anyio.get_cancelled_exc_class():
+                    break
+                continue
+            else:
+                consecutive_errors += 1
+                logger.error(
+                    f"[{mode_label}] Scanner HTTP error for {user_id}: {e} "
+                    f"({consecutive_errors}/{max_consecutive_errors})",
+                    exc_info=True,
+                )
+
         except Exception as e:
-            logger.error(f"[OAuth] Scanner error for {user_id}: {e}", exc_info=True)
+            consecutive_errors += 1
+            logger.error(
+                f"[{mode_label}] Scanner error for {user_id}: {e} "
+                f"({consecutive_errors}/{max_consecutive_errors})",
+                exc_info=True,
+            )
 
         finally:
             if nc_client:
                 await nc_client.close()
 
+        if consecutive_errors >= max_consecutive_errors:
+            logger.error(
+                f"[{mode_label}] Scanner for {user_id} hit {max_consecutive_errors} "
+                f"consecutive errors, stopping scanner"
+            )
+            break
+
         # Sleep until next interval or wake event
         try:
             with anyio.move_on_after(settings.vector_sync_scan_interval):
@@ -183,33 +324,34 @@ async def user_scanner_task(
         except anyio.get_cancelled_exc_class():
             break
 
-    logger.info(f"[OAuth] Scanner stopped for user: {user_id}")
+    logger.info(f"[{mode_label}] Scanner stopped for user: {user_id}")
 
 
-async def oauth_processor_task(
+async def multi_user_processor_task(
     worker_id: int,
     receive_stream: MemoryObjectReceiveStream[DocumentTask],
     shutdown_event: anyio.Event,
-    token_broker: "TokenBrokerService",
+    token_broker: "TokenBrokerService | None",
     nextcloud_host: str,
+    use_basic_auth: bool = False,
     *,
     task_status: TaskStatus = anyio.TASK_STATUS_IGNORED,
 ) -> None:
-    """Processor task for OAuth mode.
+    """Processor task for multi-user mode.
 
-    Handles documents from any user by fetching tokens on-demand.
+    Handles documents from any user by fetching credentials 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
+        token_broker: Token broker for OAuth mode (None for BasicAuth mode)
         nextcloud_host: Nextcloud base URL
+        use_basic_auth: If True, use app passwords; if False, use OAuth tokens
         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")
+    mode_label = "BasicAuth" if use_basic_auth else "OAuth"
+    logger.info(f"[{mode_label}] Processor {worker_id} started")
     task_status.started()
 
     while not shutdown_event.is_set():
@@ -220,9 +362,12 @@ async def oauth_processor_task(
             with anyio.fail_after(1.0):
                 doc_task = await receive_stream.receive()
 
-            # Get token for THIS document's user
+            # Get credentials for THIS document's user
             nc_client = await get_user_client(
-                doc_task.user_id, token_broker, nextcloud_host
+                doc_task.user_id,
+                token_broker,
+                nextcloud_host,
+                use_basic_auth=use_basic_auth,
             )
 
             # Process the document
@@ -232,13 +377,13 @@ async def oauth_processor_task(
             continue
 
         except anyio.EndOfStream:
-            logger.info(f"[OAuth] Processor {worker_id}: Stream closed, exiting")
+            logger.info(f"[{mode_label}] Processor {worker_id}: Stream closed, exiting")
             break
 
         except NotProvisionedError:
             if doc_task:
                 logger.warning(
-                    f"[OAuth] User {doc_task.user_id} not provisioned, "
+                    f"[{mode_label}] User {doc_task.user_id} not provisioned, "
                     f"skipping {doc_task.doc_type}_{doc_task.doc_id}"
                 )
             continue
@@ -246,18 +391,24 @@ async def oauth_processor_task(
         except Exception as e:
             if doc_task:
                 logger.error(
-                    f"[OAuth] Processor {worker_id} error processing "
+                    f"[{mode_label}] 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)
+                logger.error(
+                    f"[{mode_label}] Processor {worker_id} error: {e}", exc_info=True
+                )
 
         finally:
             if nc_client:
                 await nc_client.close()
 
-    logger.info(f"[OAuth] Processor {worker_id} stopped")
+    logger.info(f"[{mode_label}] Processor {worker_id} stopped")
+
+
+# Backward compatibility alias
+oauth_processor_task = multi_user_processor_task
 
 
 async def _run_user_scanner_with_scope(
@@ -266,9 +417,10 @@ async def _run_user_scanner_with_scope(
     send_stream: MemoryObjectSendStream[DocumentTask],
     shutdown_event: anyio.Event,
     wake_event: anyio.Event,
-    token_broker: "TokenBrokerService",
+    token_broker: "TokenBrokerService | None",
     nextcloud_host: str,
     user_states: dict[str, UserSyncState],
+    use_basic_auth: bool = False,
 ) -> None:
     """Wrapper to run scanner with cancellation scope.
 
@@ -284,6 +436,7 @@ async def _run_user_scanner_with_scope(
                 wake_event=wake_event,
                 token_broker=token_broker,
                 nextcloud_host=nextcloud_host,
+                use_basic_auth=use_basic_auth,
             )
     finally:
         # Clean up on exit
@@ -296,48 +449,60 @@ async def user_manager_task(
     send_stream: MemoryObjectSendStream[DocumentTask],
     shutdown_event: anyio.Event,
     wake_event: anyio.Event,
-    token_broker: "TokenBrokerService",
+    token_broker: "TokenBrokerService | None",
     refresh_token_storage: "RefreshTokenStorage",
     nextcloud_host: str,
     user_states: dict[str, UserSyncState],
     tg: TaskGroup,
+    use_basic_auth: bool = False,
     *,
     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
+    Periodically polls storage to detect:
+    - New users who have provisioned 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
+        token_broker: Token broker for OAuth mode (None for BasicAuth mode)
+        refresh_token_storage: Storage for tracking provisioned users
         nextcloud_host: Nextcloud base URL
         user_states: Shared dict tracking active user scanners
         tg: Task group for spawning scanner tasks
+        use_basic_auth: If True, use app passwords; if False, use OAuth tokens
         task_status: Status object for signaling task readiness
     """
     settings = get_settings()
     poll_interval = settings.vector_sync_user_poll_interval
+    mode_label = "BasicAuth" if use_basic_auth else "OAuth"
 
-    logger.info(f"[OAuth] User manager started (poll interval: {poll_interval}s)")
+    logger.info(
+        f"[{mode_label}] 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())
+            # Get current provisioned users based on mode
+            if use_basic_auth:
+                # BasicAuth mode: query app_passwords table
+                provisioned_users = set(
+                    await refresh_token_storage.get_all_app_password_user_ids()
+                )
+            else:
+                # OAuth mode: query refresh_tokens table
+                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}"
+                    f"[{mode_label}] Starting scanner for newly provisioned user: {user_id}"
                 )
                 cancel_scope = anyio.CancelScope()
                 user_states[user_id] = UserSyncState(
@@ -356,24 +521,27 @@ async def user_manager_task(
                     token_broker,
                     nextcloud_host,
                     user_states,
+                    use_basic_auth,  # Positional after 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}")
+                logger.info(
+                    f"[{mode_label}] 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)")
+                logger.info(f"[{mode_label}] Started {len(new_users)} new scanner(s)")
             if revoked_users:
-                logger.info(f"[OAuth] Stopped {len(revoked_users)} scanner(s)")
+                logger.info(f"[{mode_label}] Stopped {len(revoked_users)} scanner(s)")
 
         except Exception as e:
-            logger.error(f"[OAuth] User manager error: {e}", exc_info=True)
+            logger.error(f"[{mode_label}] User manager error: {e}", exc_info=True)
 
         # Sleep until next poll
         try:
@@ -384,9 +552,9 @@ async def user_manager_task(
 
     # Cancel all remaining scanners on shutdown
     logger.info(
-        f"[OAuth] User manager shutting down, cancelling {len(user_states)} scanner(s)"
+        f"[{mode_label}] 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")
+    logger.info(f"[{mode_label}] User manager stopped")

nextcloud_mcp_server/vector/placeholder.py

@@ -21,6 +21,7 @@ import logging
 import time
 import uuid
 
+from qdrant_client import models
 from qdrant_client.models import FieldCondition, Filter, MatchValue, PointStruct
 
 from nextcloud_mcp_server.config import get_settings
@@ -82,8 +83,6 @@ async def write_placeholder_point(
 
         # Create empty sparse vector for placeholders
         # Use models.SparseVector with empty indices/values
-        from qdrant_client import models
-
         empty_sparse = models.SparseVector(indices=[], values=[])
 
         # Generate deterministic point ID

nextcloud_mcp_server/vector/processor.py

@@ -3,6 +3,7 @@
 Processes documents from stream: fetches content, generates embeddings, stores in Qdrant.
 """
 
+import base64
 import logging
 import time
 import uuid
@@ -16,6 +17,7 @@ from qdrant_client.models import FieldCondition, Filter, MatchValue, PointStruct
 
 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.document_processors import get_registry
 from nextcloud_mcp_server.embedding import get_bm25_service, get_embedding_service
 from nextcloud_mcp_server.observability.metrics import (
     record_qdrant_operation,
@@ -23,7 +25,9 @@ from nextcloud_mcp_server.observability.metrics import (
     update_vector_sync_queue_size,
 )
 from nextcloud_mcp_server.observability.tracing import trace_operation
+from nextcloud_mcp_server.search.pdf_highlighter import PDFHighlighter
 from nextcloud_mcp_server.vector.document_chunker import DocumentChunker
+from nextcloud_mcp_server.vector.html_processor import html_to_markdown
 from nextcloud_mcp_server.vector.placeholder import delete_placeholder_point
 from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
 from nextcloud_mcp_server.vector.scanner import DocumentTask
@@ -274,8 +278,6 @@ async def _index_document(
             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", ""))
@@ -436,8 +438,6 @@ async def _index_document(
             },
         ):
             # Use document processor registry to extract text
-            from nextcloud_mcp_server.document_processors import get_registry
-
             registry = get_registry()
 
             try:
@@ -585,10 +585,6 @@ async def _index_document(
                 "vector_sync.pdf_size": len(content_bytes),
             },
         ):
-            import base64
-
-            from nextcloud_mcp_server.search.pdf_highlighter import PDFHighlighter
-
             # Build chunk data for batch processing
             # Format: (chunk_index, start_offset, end_offset, page_number, chunk_text)
             chunk_data: list[tuple[int, int, int, int | None, str]] = [

nextcloud_mcp_server/vector/qdrant_client.py

@@ -6,6 +6,7 @@ from qdrant_client import AsyncQdrantClient, models
 from qdrant_client.models import Distance, VectorParams
 
 from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.embedding import get_embedding_service
 
 logger = logging.getLogger(__name__)
 
@@ -62,9 +63,6 @@ async def get_qdrant_client() -> AsyncQdrantClient:
         # Get collection name (auto-generated from deployment ID + model)
         collection_name = settings.get_collection_name()
 
-        # Import here to avoid circular dependency
-        from nextcloud_mcp_server.embedding import get_embedding_service
-
         embedding_service = get_embedding_service()
 
         # Detect dimension dynamically (for OllamaEmbeddingProvider)