bump: version 0.61.2 → 0.61.3

fix(astrolabe): update Vue component bindings for Vue 3 compatibility

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

@@ -17,7 +17,7 @@ jobs:
 
     steps:
       - name: Checkout code
-        uses: actions/checkout@v4
+        uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5 # v4
 
       - name: Get version from tag
         id: tag
@@ -35,18 +35,18 @@ jobs:
           echo "Version validated: $INFO_VERSION"
 
       - name: Setup Node
-        uses: actions/setup-node@v4
+        uses: actions/setup-node@49933ea5288caeca8642d1e84afbd3f7d6820020 # v4
         with:
           node-version: 22
 
       - name: Setup PHP
-        uses: shivammathur/setup-php@v2
+        uses: shivammathur/setup-php@44454db4f0199b8b9685a5d763dc37cbf79108e1 # v2
         with:
           php-version: 8.1
           coverage: none
 
       - name: Checkout Nextcloud server (for signing)
-        uses: actions/checkout@v4
+        uses: actions/checkout@34e114876b0b11c390a56381ad16ebd13914f8d5 # v4
         with:
           repository: nextcloud/server
           ref: stable30
@@ -70,7 +70,7 @@ jobs:
         run: make appstore server_dir=${{ github.workspace }}/server
 
       - name: Create GitHub release and attach tarball
-        uses: svenstaro/upload-release-action@v2
+        uses: svenstaro/upload-release-action@6b7fa9f267e90b50a19fef07b3596790bb941741 # v2
         with:
           repo_token: ${{ secrets.GITHUB_TOKEN }}
           file: ${{ env.APP_DIR }}/build/artifacts/${{ env.APP_NAME }}.tar.gz
@@ -80,7 +80,7 @@ jobs:
           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@v1.0.4
+        uses: R0Wi/nextcloud-appstore-push-action@9244bb5445776688cfe90fa1903ea8dff95b0c28 # v1.0.4
         with:
           app_name: ${{ env.APP_NAME }}
           appstore_token: ${{ secrets.APPSTORE_TOKEN }}

.github/workflows/bump-version.yml

@@ -21,7 +21,7 @@ jobs:
           token: "${{ secrets.PERSONAL_ACCESS_TOKEN }}"
 
       - name: Set up Python
-        uses: actions/setup-python@v5
+        uses: actions/setup-python@a26af69be951a213d495a4c3e4e4022e16d87065 # v5
         with:
           python-version: '3.11'
 
@@ -87,21 +87,32 @@ jobs:
           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)
 
+          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..."
+            HELM_HAS_COMMITS=true
+          fi
+
+          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
 
           # Bump Astrolabe (scope: astrolabe)
@@ -130,29 +141,36 @@ jobs:
           echo "Pushed tags for components:${{ steps.bump.outputs.components }}"
 
       - name: Summary
-        if: steps.bump.outputs.bumped == 'true'
         run: |
-          echo "## Version Bump Summary" >> $GITHUB_STEP_SUMMARY
-          echo "" >> $GITHUB_STEP_SUMMARY
-          echo "The following components were bumped:" >> $GITHUB_STEP_SUMMARY
-          echo "" >> $GITHUB_STEP_SUMMARY
+          if [ "${{ steps.bump.outputs.bumped }}" == "true" ]; then
+            echo "## Version Bump Summary" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "The following components were bumped:" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
 
-          for component in ${{ steps.bump.outputs.components }}; do
-            case $component in
-              mcp)
-                tag=$(git tag --sort=-creatordate | grep -E '^v[0-9]' | head -n 1)
-                echo "- **MCP Server**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
-                ;;
-              helm)
-                tag=$(git tag --sort=-creatordate | grep -E '^nextcloud-mcp-server-' | head -n 1)
-                echo "- **Helm Chart**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
-                ;;
-              astrolabe)
-                tag=$(git tag --sort=-creatordate | grep -E '^astrolabe-v' | head -n 1)
-                echo "- **Astrolabe**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
-                ;;
-            esac
-          done
+            for component in ${{ steps.bump.outputs.components }}; do
+              case $component in
+                mcp)
+                  tag=$(git tag --sort=-creatordate | grep -E '^v[0-9]' | head -n 1)
+                  echo "- **MCP Server**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
+                  ;;
+                helm)
+                  tag=$(git tag --sort=-creatordate | grep -E '^nextcloud-mcp-server-' | head -n 1)
+                  echo "- **Helm Chart**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
+                  ;;
+                astrolabe)
+                  tag=$(git tag --sort=-creatordate | grep -E '^astrolabe-v' | head -n 1)
+                  echo "- **Astrolabe**: \`$tag\`" >> $GITHUB_STEP_SUMMARY
+                  ;;
+              esac
+            done
 
-          echo "" >> $GITHUB_STEP_SUMMARY
-          echo "Tags have been pushed and release workflows will trigger automatically." >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "Tags have been pushed and release workflows will trigger automatically." >> $GITHUB_STEP_SUMMARY
+          else
+            echo "## Version Bump Summary" >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "✅ No version bumps required - no relevant commits found since last release." >> $GITHUB_STEP_SUMMARY
+            echo "" >> $GITHUB_STEP_SUMMARY
+            echo "The workflow completed successfully with no changes." >> $GITHUB_STEP_SUMMARY
+          fi

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

@@ -33,7 +33,7 @@ jobs:
 
       - name: Run Claude Code Review
         id: claude-review
-        uses: anthropics/claude-code-action@d7b6d50442a89f005016e778bf825a72ef582525 # v1
+        uses: anthropics/claude-code-action@1b8ee3b94104046d71fde52ec3557651ad8c0d71 # v1.0.29
         with:
           claude_code_oauth_token: ${{ secrets.CLAUDE_CODE_OAUTH_TOKEN }}
           prompt: |

.github/workflows/claude.yml

@@ -32,7 +32,7 @@ jobs:
 
       - name: Run Claude Code
         id: claude
-        uses: anthropics/claude-code-action@d7b6d50442a89f005016e778bf825a72ef582525 # v1
+        uses: anthropics/claude-code-action@1b8ee3b94104046d71fde52ec3557651ad8c0d71 # v1.0.29
         with:
           claude_code_oauth_token: ${{ secrets.CLAUDE_CODE_OAUTH_TOKEN }}
 

.github/workflows/helm-release.yml

@@ -4,6 +4,7 @@ on:
   push:
     tags:
       - v*
+      - nextcloud-mcp-server-*
 
 jobs:
   release:

.github/workflows/rag-evaluation.yml

@@ -27,7 +27,7 @@ jobs:
       - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
 
       - name: Run docker compose with vector sync
-        uses: hoverkraft-tech/compose-action@248470ecc5ed40d8ed3d4480d8260d77179ef579 # v2.4.2
+        uses: hoverkraft-tech/compose-action@05da55b2bb8a5a759d1c4732095044bd9018c050 # v2.4.3
         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@61cb8a9741eeb8a550a1b8544337180c0fc8476b # v7.2.0
 
       - name: Wait for Nextcloud to be ready
         run: |

.github/workflows/release.yml

@@ -20,7 +20,7 @@ jobs:
       - name: Checkout
         uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6
       - name: Install uv
-        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
+        uses: astral-sh/setup-uv@61cb8a9741eeb8a550a1b8544337180c0fc8476b # v7.2.0
       - name: Install Python 3.11
         run: uv python install 3.11
       - name: Build

.github/workflows/test.yml

@@ -11,7 +11,7 @@ jobs:
     steps:
       - uses: actions/checkout@8e8c483db84b4bee98b60c0593521ed34d9990e8 # v6.0.1
       - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@681c641aba71e4a1c380be3ab5e12ad51f415867 # v7.1.6
+        uses: astral-sh/setup-uv@61cb8a9741eeb8a550a1b8544337180c0fc8476b # v7.2.0
       - name: Check format
         run: |
           uv run --frozen ruff format --diff
@@ -48,15 +48,32 @@ jobs:
       ###### Required to build OIDC App ######
 
 
+      ###### Required to build Astrolabe App ######
+
+      - name: Set up Node.js for Astrolabe
+        uses: actions/setup-node@39370e3970a6d050c480ffad4ff0ed4d3fdee5af # v4.1.0
+        with:
+          node-version: '20'
+
+      - name: Build Astrolabe app
+        run: |
+          cd third_party/astrolabe
+          composer install --no-dev --optimize-autoloader
+          npm ci
+          npm run build
+
+      ###### Required to build Astrolabe App ######
+
+
       - name: Run docker compose
-        uses: hoverkraft-tech/compose-action@248470ecc5ed40d8ed3d4480d8260d77179ef579 # v2.4.2
+        uses: hoverkraft-tech/compose-action@05da55b2bb8a5a759d1c4732095044bd9018c050 # v2.4.3
         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@61cb8a9741eeb8a550a1b8544337180c0fc8476b # v7.2.0
 
       - name: Install Playwright dependencies
         run: |

CHANGELOG.md

@@ -5,6 +5,132 @@ 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/).
 
+## v0.61.3 (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

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:d75c4b6cdd039ae966a34cd3ccab9e0e5f7299280ad76fe1744882d86eedce0b
 
-COPY --from=ghcr.io/astral-sh/uv:0.9.18@sha256:5713fa8217f92b80223bc83aac7db36ec80a84437dbc0d04bbc659cae030d8c9 /uv /uvx /bin/
+COPY --from=ghcr.io/astral-sh/uv:0.9.25@sha256:13e233d08517abdafac4ead26c16d881cd77504a2c40c38c905cf3a0d70131a6 /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:d75c4b6cdd039ae966a34cd3ccab9e0e5f7299280ad76fe1744882d86eedce0b
 
 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:0.9.25@sha256:13e233d08517abdafac4ead26c16d881cd77504a2c40c38c905cf3a0d70131a6 /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

@@ -2,7 +2,7 @@
 
 set -euox pipefail
 
-echo "Installing and configuring Astrolabe app for testing..."
+echo "Installing Astrolabe app for testing..."
 
 # Check if development astrolabe app is mounted at /opt/apps/astrolabe
 if [ -d /opt/apps/astrolabe ]; then
@@ -30,55 +30,7 @@ else
     php /var/www/html/occ app:enable astrolabe
 fi
 
-# Configure MCP server URLs in Nextcloud system config
-# - mcp_server_url: Internal URL for PHP app to call MCP server APIs (Docker internal network)
-# - mcp_server_public_url: Public URL for OAuth token audience (what browsers/MCP clients see)
-php /var/www/html/occ config:system:set mcp_server_url --value='http://mcp-oauth:8001'
-php /var/www/html/occ config:system:set mcp_server_public_url --value='http://localhost:8001'
-
-# Create OAuth client for Astrolabe app
-# The resource_url MUST match what the MCP server expects as token audience
-# This allows tokens from this client to be validated by MCP server's UnifiedTokenVerifier
-MCP_CLIENT_ID="nextcloudMcpServerUIPublicClient"
-MCP_RESOURCE_URL="http://localhost:8001"
-MCP_REDIRECT_URI="http://localhost:8080/apps/astrolabe/oauth/callback"
-
-echo "Configuring OAuth client for Astrolabe..."
-
-# Check if client already exists
-if php /var/www/html/occ oidc:list 2>/dev/null | grep -q "$MCP_CLIENT_ID"; then
-    echo "OAuth client $MCP_CLIENT_ID already exists, removing to recreate with correct settings..."
-    php /var/www/html/occ oidc:remove "$MCP_CLIENT_ID" || true
-fi
-
-# Create OAuth client with correct resource_url for MCP server audience
-echo "Creating OAuth confidential client with resource_url=$MCP_RESOURCE_URL"
-CLIENT_OUTPUT=$(php /var/www/html/occ oidc:create \
-    "Astrolabe" \
-    "$MCP_REDIRECT_URI" \
-    --client_id="$MCP_CLIENT_ID" \
-    --type=confidential \
-    --flow=code \
-    --token_type=jwt \
-    --resource_url="$MCP_RESOURCE_URL" \
-    --allowed_scopes="openid profile email offline_access notes:read notes:write calendar:read calendar:write contacts:read contacts:write cookbook:read cookbook:write deck:read deck:write tables:read tables:write files:read files:write")
-
-echo "$CLIENT_OUTPUT"
-
-# Extract client_secret from JSON output
-CLIENT_SECRET=$(echo "$CLIENT_OUTPUT" | php -r 'echo json_decode(file_get_contents("php://stdin"), true)["client_secret"] ?? "";')
-
-if [ -n "$CLIENT_SECRET" ]; then
-    echo "Configuring Astrolabe client secret in system config..."
-    php /var/www/html/occ config:system:set astrolabe_client_secret --value="$CLIENT_SECRET"
-    echo "✓ Client secret configured: ${CLIENT_SECRET:0:8}..."
-else
-    echo "⚠ Warning: Could not extract client_secret from OIDC client creation"
-fi
-
-# Configure OAuth client ID in system config
-echo "Configuring Astrolabe client ID in system config..."
-php /var/www/html/occ config:system:set astrolabe_client_id --value="$MCP_CLIENT_ID"
-echo "✓ Client ID configured: $MCP_CLIENT_ID"
-
-echo "Astrolabe app installed and configured 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 = "0.57.1"
 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 +14,120 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Configurable resource limits
 - Grafana dashboard annotations
 
+## nextcloud-mcp-server-0.57.1 (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: 1.16.3
 - name: ollama
   repository: https://otwld.github.io/ollama-helm
-  version: 1.36.0
-digest: sha256:fab8008217b27ff4e3e139c2f481eedaa23f9f64a3a086d0e9deea2195b69b63
-generated: "2025-12-14T11:07:07.024787592Z"
+  version: 1.37.0
+digest: sha256:0ce3bb4b5e95a3b8fde3f5f374d7b62aeafcb0dcf8a60b9d95978530b6c05b68
+generated: "2026-01-08T11:11:12.857375888Z"

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: 0.57.1
+appVersion: "0.61.3"
 keywords:
   - nextcloud
   - mcp
@@ -27,10 +27,10 @@ annotations:
   grafana_dashboard_folder: "Nextcloud MCP"
 dependencies:
   - name: qdrant
-    version: "1.16.2"
+    version: "1.16.3"
     repository: https://qdrant.github.io/qdrant-helm
     condition: qdrant.networkMode.deploySubchart
   - name: ollama
-    version: "1.36.0"
+    version: "1.37.0"
     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
 
@@ -208,16 +208,16 @@ 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 +427,7 @@ 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 +459,7 @@ 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 +537,8 @@ 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 +576,7 @@ ollama:
 Or use an external Ollama instance:
 
 ```yaml
-vectorSync:
+semanticSearch:
   enabled: true
 
 qdrant:
@@ -592,7 +592,7 @@ ollama:
 Or use OpenAI for embeddings:
 
 ```yaml
-vectorSync:
+semanticSearch:
   enabled: true
 
 qdrant:
@@ -689,7 +689,9 @@ 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 }}

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

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

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

@@ -68,7 +68,7 @@ spec:
             - name: NEXTCLOUD_HOST
               value: {{ .Values.nextcloud.host | quote }}
             {{- if eq .Values.auth.mode "basic" }}
-            # Basic auth mode
+            # Basic auth mode (single-user)
             - name: NEXTCLOUD_USERNAME
               valueFrom:
                 secretKeyRef:
@@ -79,6 +79,41 @@ spec:
                 secretKeyRef:
                   name: {{ include "nextcloud-mcp-server.basicAuthSecretName" . }}
                   key: {{ .Values.auth.basic.passwordKey }}
+            {{- else if eq .Values.auth.mode "multi-user-basic" }}
+            # Multi-user BasicAuth mode (pass-through)
+            - name: ENABLE_MULTI_USER_BASIC_AUTH
+              value: "true"
+            - name: NEXTCLOUD_MCP_SERVER_URL
+              value: {{ include "nextcloud-mcp-server.mcpServerUrl" . | quote }}
+            - name: NEXTCLOUD_PUBLIC_ISSUER_URL
+              value: {{ include "nextcloud-mcp-server.publicIssuerUrl" . | quote }}
+            {{- if .Values.auth.multiUserBasic.enableOfflineAccess }}
+            # Background operations with app passwords (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
@@ -251,6 +286,10 @@ spec:
             - name: oauth-storage
               mountPath: /app/.oauth
             {{- end }}
+            {{- if and (eq .Values.auth.mode "multi-user-basic") .Values.auth.multiUserBasic.enableOfflineAccess .Values.auth.multiUserBasic.persistence.enabled }}
+            - name: token-storage
+              mountPath: /app/data
+            {{- end }}
             {{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled }}
             - name: qdrant-data
               mountPath: /app/data
@@ -266,6 +305,11 @@ spec:
           persistentVolumeClaim:
             claimName: {{ include "nextcloud-mcp-server.oauthPvcName" . }}
         {{- end }}
+        {{- if and (eq .Values.auth.mode "multi-user-basic") .Values.auth.multiUserBasic.enableOfflineAccess .Values.auth.multiUserBasic.persistence.enabled }}
+        - name: token-storage
+          persistentVolumeClaim:
+            claimName: {{ include "nextcloud-mcp-server.multiUserBasicPvcName" . }}
+        {{- end }}
         {{- if and (eq .Values.qdrant.mode "persistent") .Values.qdrant.localPersistence.enabled }}
         - name: qdrant-data
           persistentVolumeClaim:

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

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

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

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

charts/nextcloud-mcp-server/values.yaml

@@ -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"
@@ -316,10 +365,11 @@ 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 +380,7 @@ 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

@@ -8,6 +8,8 @@ services:
     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
@@ -21,10 +23,10 @@ services:
     restart: always
 
   app:
-    image: docker.io/library/nextcloud:32.0.3@sha256:53231a9fb9233af2c15bfe70fc03ebe639fd53243fa42a9369884b1e0008deae
+    image: docker.io/library/nextcloud:32.0.3@sha256:1a75afcd53b38aa72205ab38a66121ed9f9e8c99f4e70b0dccc858e60ad57b7d
     restart: always
     ports:
-      - 0.0.0.0:8080:80
+      - 127.0.0.1:8080:80
     depends_on:
       - redis
       - db
@@ -35,7 +37,7 @@ 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
+      - ./third_party/astrolabe:/opt/apps/astrolabe:ro
     environment:
       - NEXTCLOUD_TRUSTED_DOMAINS=app
       - NEXTCLOUD_ADMIN_USER=admin
@@ -52,14 +54,14 @@ services:
       retries: 30
 
   recipes:
-    image: docker.io/library/nginx:alpine@sha256:052b75ab72f690f33debaa51c7e08d9b969a0447a133eb2b99cc905d9188cb2b
+    image: docker.io/library/nginx:alpine@sha256:66d420cc54ef85bcc1d72220e83d7aaa6c4850bd2904794e3a56f09fd4ccb66e
     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:db5fcc831eb673ec835c41e8d47f993fdde276562285d6837cebb03f958536a2
     restart: always
     ports:
       - 127.0.0.1:8002:8000
@@ -86,8 +88,8 @@ 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
 
@@ -123,6 +125,40 @@ services:
       # - DOCUMENT_CHUNK_SIZE=512      # Words per chunk (default: 512)
       # - DOCUMENT_CHUNK_OVERLAP=50    # Overlapping words (default: 50, recommended: 10-20% of chunk size)
 
+  mcp-multi-user-basic:
+    build: .
+    restart: always
+    command: ["--transport", "streamable-http"]
+    depends_on:
+      app:
+        condition: service_healthy
+    ports:
+      - 127.0.0.1:8003:8000
+    environment:
+      # Multi-user BasicAuth pass-through mode (ADR-020)
+      - NEXTCLOUD_HOST=http://app:80
+      - NEXTCLOUD_MCP_SERVER_URL=http://localhost:8003
+      - NEXTCLOUD_PUBLIC_ISSUER_URL=http://localhost:8080
+      - ENABLE_MULTI_USER_BASIC_AUTH=true
+      - ENABLE_BACKGROUND_OPERATIONS=true
+
+      # Token storage (required for middleware initialization)
+      - TOKEN_ENCRYPTION_KEY=ESF1BvEQdGYsCluwMx9Cxvw3uh5pFowPH7Rg_nIliyo=
+      - TOKEN_STORAGE_DB=/app/data/tokens.db
+
+      - 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:
+      - multi-user-basic-data:/app/data
+
   mcp-oauth:
     build: .
     command: ["--transport", "streamable-http", "--oauth", "--port", "8001", "--oauth-token-type", "jwt"]
@@ -143,7 +179,7 @@ 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
 
@@ -151,14 +187,19 @@ services:
       # Tokens must contain BOTH MCP and Nextcloud audiences
       # No token exchange needed - tokens work for both MCP auth and Nextcloud APIs
 
-      # Vector sync configuration (ADR-007)
-      - VECTOR_SYNC_ENABLED=true
+      # Semantic search configuration (ADR-007, ADR-021)
+      - ENABLE_SEMANTIC_SEARCH=true
       - VECTOR_SYNC_SCAN_INTERVAL=60
       - VECTOR_SYNC_PROCESSOR_WORKERS=1
 
       # Qdrant configuration - persistent local storage
       - QDRANT_LOCATION=/app/data/qdrant
 
+      # Embedding provider for vector sync (use Simple provider as fallback)
+      # Ollama not available in CI/test environments
+      # - OLLAMA_BASE_URL=http://ollama:11434
+      # - OLLAMA_EMBEDDING_MODEL=nomic-embed-text
+
       # NO admin credentials - using OAuth with Dynamic Client Registration (DCR)
       # Client credentials registered via RFC 7591 and stored in volume
       # JWT token type is used for testing (faster validation, scopes embedded in token)
@@ -167,7 +208,7 @@ services:
       - oauth-tokens:/app/data
 
   keycloak:
-    image: quay.io/keycloak/keycloak:26.4.7@sha256:9409c59bdfb65dbffa20b11e6f18b8abb9281d480c7ca402f51ed3d5977e6007
+    image: quay.io/keycloak/keycloak:26.5.0@sha256:5fdd7cda82e58775ed124294c7e16fabc33166d38dfc4aabebda7d64e7a964bf
     command:
       - "start-dev"
       - "--import-realm"
@@ -215,7 +256,7 @@ 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
 
@@ -248,13 +289,13 @@ 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:v1.16.3@sha256:0425e3e03e7fd9b3dc95c4214546afe19de2eb2e28ca621441a56663ac6e1f46
     restart: always
     ports:
       - 127.0.0.1:6333:6333  # REST API
@@ -280,3 +321,4 @@ volumes:
   keycloak-oauth-storage:
   qdrant-data:
   mcp-data:
+  multi-user-basic-data:

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

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

docs/ADR-021-configuration-consolidation.md

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

docs/authentication.md

@@ -140,6 +140,93 @@ 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 |
+
+### 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
@@ -110,8 +173,50 @@ NEXTCLOUD_PASSWORD=your_app_password_or_password
 
 ## Semantic Search Configuration (Optional)
 
+**New in v0.58.0:** Simplified semantic search configuration with automatic dependency resolution.
+
 The MCP server includes semantic search capabilities powered by vector embeddings. This feature requires a vector database (Qdrant) and an embedding service.
 
+### Quick Start
+
+**Single-User Mode:**
+```dotenv
+NEXTCLOUD_HOST=http://localhost:8080
+NEXTCLOUD_USERNAME=admin
+NEXTCLOUD_PASSWORD=password
+
+# Enable semantic search
+ENABLE_SEMANTIC_SEARCH=true
+
+# Vector database
+QDRANT_LOCATION=:memory:
+
+# Embedding provider
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+**Multi-User OAuth Mode:**
+```dotenv
+NEXTCLOUD_HOST=https://nextcloud.example.com
+MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# Enable semantic search
+# In multi-user modes, this AUTOMATICALLY enables background operations!
+ENABLE_SEMANTIC_SEARCH=true
+
+# Required for background operations (auto-enabled by semantic search)
+TOKEN_ENCRYPTION_KEY=your-key-here
+TOKEN_STORAGE_DB=/app/data/tokens.db
+
+# Vector database
+QDRANT_URL=http://qdrant:6333
+
+# Embedding provider
+OLLAMA_BASE_URL=http://ollama:11434
+```
+
+> **Note:** In multi-user modes (OAuth, Multi-User BasicAuth), enabling `ENABLE_SEMANTIC_SEARCH` automatically enables background operations and refresh token storage. You don't need to set `ENABLE_BACKGROUND_OPERATIONS` separately!
+
 ### Qdrant Vector Database Modes
 
 The server supports three Qdrant deployment modes:
@@ -126,7 +231,7 @@ No configuration needed! If neither `QDRANT_URL` nor `QDRANT_LOCATION` is set, t
 
 ```dotenv
 # No Qdrant configuration needed - defaults to :memory:
-VECTOR_SYNC_ENABLED=true
+ENABLE_SEMANTIC_SEARCH=true
 ```
 
 **Pros:**
@@ -145,7 +250,7 @@ For single-instance deployments that need persistence without a separate Qdrant
 ```dotenv
 # Local persistent storage
 QDRANT_LOCATION=/app/data/qdrant  # Or any writable path
-VECTOR_SYNC_ENABLED=true
+ENABLE_SEMANTIC_SEARCH=true
 ```
 
 **Pros:**
@@ -166,7 +271,7 @@ For production deployments with a dedicated Qdrant service:
 QDRANT_URL=http://qdrant:6333
 QDRANT_API_KEY=your-secret-api-key  # Optional
 QDRANT_COLLECTION=nextcloud_content  # Optional
-VECTOR_SYNC_ENABLED=true
+ENABLE_SEMANTIC_SEARCH=true
 ```
 
 **Pros:**
@@ -283,13 +388,15 @@ Solutions:
 - Data corruption in Qdrant
 - Confusing error messages during indexing
 
-### Vector Sync Configuration
+### Background Indexing Configuration
 
 Control background indexing behavior:
 
 ```dotenv
-# Vector sync settings (ADR-007)
-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 +406,8 @@ DOCUMENT_CHUNK_SIZE=512               # Words per chunk (default: 512)
 DOCUMENT_CHUNK_OVERLAP=50             # Overlapping words between chunks (default: 50)
 ```
 
+> **Note:** The `VECTOR_SYNC_*` tuning parameters keep their names as they're implementation details. Only the user-facing feature flag was renamed to `ENABLE_SEMANTIC_SEARCH`.
+
 ### Embedding Service Configuration
 
 The server uses an embedding service to generate vector representations. Two options are available:
@@ -369,11 +478,11 @@ DOCUMENT_CHUNK_OVERLAP=100
 
 | Variable | Required | Default | Description |
 |----------|----------|---------|-------------|
+| `ENABLE_SEMANTIC_SEARCH` | ⚠️ Optional | `false` | Enable semantic search with background indexing (replaces `VECTOR_SYNC_ENABLED`) |
 | `QDRANT_URL` | ⚠️ Optional | - | Qdrant service URL (network mode) - mutually exclusive with `QDRANT_LOCATION` |
 | `QDRANT_LOCATION` | ⚠️ Optional | `:memory:` | Local Qdrant path (`:memory:` or `/path/to/data`) - mutually exclusive with `QDRANT_URL` |
 | `QDRANT_API_KEY` | ⚠️ Optional | - | Qdrant API key (network mode only) |
-| `QDRANT_COLLECTION` | ⚠️ Optional | `nextcloud_content` | Qdrant collection name |
-| `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 +492,9 @@ DOCUMENT_CHUNK_OVERLAP=100
 | `DOCUMENT_CHUNK_SIZE` | ⚠️ Optional | `512` | Words per chunk for document embedding |
 | `DOCUMENT_CHUNK_OVERLAP` | ⚠️ Optional | `50` | Overlapping words between chunks (must be < chunk size) |
 
+**Deprecated variables (still functional):**
+- `VECTOR_SYNC_ENABLED` - Use `ENABLE_SEMANTIC_SEARCH` instead (will be removed in v1.0.0)
+
 ### Docker Compose Example
 
 Enable network mode Qdrant with docker-compose:
@@ -392,7 +504,7 @@ services:
   mcp:
     environment:
       - QDRANT_URL=http://qdrant:6333
-      - VECTOR_SYNC_ENABLED=true
+      - ENABLE_SEMANTIC_SEARCH=true
 
   qdrant:
     image: qdrant/qdrant:latest
@@ -545,6 +657,7 @@ uv run nextcloud-mcp-server --no-oauth \
 
 ## See Also
 
+- [Configuration Migration Guide v2](configuration-migration-v2.md) - **New in v0.58.0:** Migrate from old variable names
 - [OAuth Quick Start](quickstart-oauth.md) - 5-minute OAuth setup for development
 - [OAuth Setup Guide](oauth-setup.md) - Detailed OAuth configuration for production
 - [OAuth Architecture](oauth-architecture.md) - How OAuth works in the MCP server
@@ -553,3 +666,4 @@ uv run nextcloud-mcp-server --no-oauth \
 - [Running the Server](running.md) - Starting the server with different configurations
 - [Troubleshooting](troubleshooting.md) - Common configuration issues
 - [OAuth Troubleshooting](oauth-troubleshooting.md) - OAuth-specific troubleshooting
+- [ADR-021](ADR-021-configuration-consolidation.md) - Configuration consolidation architecture decision

docs/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 +1,357 @@
+# 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** 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 "$MCP_URL/webhooks/nextcloud"
+```
+
+## Webhook Presets (via Astrolabe UI)
+
+The Astrolabe app provides preset webhook configurations that can be enabled/disabled via the Admin settings UI:
+
+| Preset | Events Covered |
+|--------|----------------|
+| `notes_sync` | File create/update/delete for .md files |
+| `calendar_sync` | Calendar object events |
+| `tables_sync` | Tables row events |
+| `forms_sync` | Forms submission events |
+| `files_sync` | All file events (optional, high volume) |
+
+**Enable Presets:**
+1. Navigate to **Nextcloud Settings → Astrolabe** (Admin settings)
+2. Toggle desired presets in "Webhook Configuration"
+
+**Note:** Presets require the MCP server's management API to be accessible. The API uses OAuth bearer tokens from the user's session.
+
+## Security Considerations
+
+### Webhook Authentication
+Configure `WEBHOOK_SECRET` to require authentication for incoming webhooks:
+
+```bash
+# MCP Server
+WEBHOOK_SECRET=<generate-random-secret>
+
+# Nextcloud webhook registration
+php occ webhook_listeners:add \
+  --event "..." \
+  --uri "$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 in Astrolabe
+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 +1,236 @@
-# Nextcloud Instance
+# ============================================
+# DEPLOYMENT MODE SELECTION
+# ============================================
+# Optional: Explicitly declare deployment mode (ADR-021)
+# If not set, mode is auto-detected from other settings
+# Valid values: single_user_basic, multi_user_basic, oauth_single_audience,
+#               oauth_token_exchange, smithery
+#
+# Recommendation: Set this for clarity and to catch configuration errors early
+#MCP_DEPLOYMENT_MODE=oauth_single_audience
+
+# ============================================
+# COMMON SETTINGS (Required for all modes)
+# ============================================
+# Your Nextcloud instance URL (without trailing slash)
 NEXTCLOUD_HOST=
 
-# ===== AUTHENTICATION MODE =====
-# Choose ONE of the following:
-
-# 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
+
+# ===== 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/management.py

@@ -10,12 +10,18 @@ All endpoints use OAuth bearer token authentication via UnifiedTokenVerifier.
 The PHP app obtains tokens through PKCE flow and uses them to access these endpoints.
 """
 
+import base64
 import logging
-import os
+import re
 import time
+from collections import defaultdict
 from importlib.metadata import version
-from typing import Any
+from typing import TYPE_CHECKING, Any
 
+import httpx
+
+if TYPE_CHECKING:
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from starlette.requests import Request
 from starlette.responses import JSONResponse
 
@@ -25,6 +31,23 @@ logger = logging.getLogger(__name__)
 # Get package version from metadata
 __version__ = version("nextcloud-mcp-server")
 
+# 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)
+
 # Track server start time for uptime calculation
 _server_start_time = time.time()
 
@@ -55,6 +78,22 @@ async def validate_token_and_get_user(
 ) -> tuple[str, dict[str, Any]]:
     """Validate OAuth bearer token and extract user ID.
 
+    Uses verify_token_for_management_api which accepts any valid Nextcloud OIDC
+    token (not just MCP-audience tokens). This is needed because Astrolabe
+    (NC PHP app) uses its own OAuth client, separate from MCP server's client.
+
+    Security Model:
+    ~~~~~~~~~~~~~~~
+    - **Authentication** (this function): Verifies token is cryptographically valid
+      and extracts user identity from the `sub` claim.
+    - **Authorization** (calling endpoints): Each endpoint MUST verify that the
+      authenticated user owns the requested resource. For example:
+      - GET /users/{user_id}/session: Checks token_user_id == path_user_id (403 if mismatch)
+      - POST /users/{user_id}/revoke: Checks token_user_id == path_user_id (403 if mismatch)
+
+    This separation ensures that even without audience validation, users can only
+    access their own resources. Cross-user access is blocked at the authorization layer.
+
     Args:
         request: Starlette request with Authorization header
 
@@ -72,9 +111,10 @@ async def validate_token_and_get_user(
     # Note: This is set in app.py starlette_lifespan for OAuth mode
     token_verifier = request.app.state.oauth_context["token_verifier"]
 
-    # Validate token (handles both JWT and opaque tokens)
-    # verify_token returns AccessToken object or None
-    access_token = await token_verifier.verify_token(token)
+    # Validate token for management API (handles both JWT and opaque tokens)
+    # Uses verify_token_for_management_api which accepts any valid Nextcloud token
+    # without requiring MCP audience - needed for Astrolabe integration (ADR-018)
+    access_token = await token_verifier.verify_token_for_management_api(token)
 
     if not access_token:
         raise ValueError("Token validation failed")
@@ -164,6 +204,141 @@ def _validate_query_string(query: str, max_length: int = 10000) -> None:
         raise ValueError(f"Query too long: maximum {max_length} characters")
 
 
+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
+    """
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+
+    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
+
+
+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_server_status(request: Request) -> JSONResponse:
     """GET /api/v1/status - Server status and version.
 
@@ -182,14 +357,23 @@ async def get_server_status(request: Request) -> JSONResponse:
     # Calculate uptime
     uptime_seconds = int(time.time() - _server_start_time)
 
-    # Determine auth mode
-    nextcloud_username = os.getenv("NEXTCLOUD_USERNAME")
-    nextcloud_password = os.getenv("NEXTCLOUD_PASSWORD")
+    # Determine auth mode using proper mode detection
+    from nextcloud_mcp_server.config_validators import AuthMode, detect_auth_mode
 
-    if nextcloud_username and nextcloud_password:
-        auth_mode = "basic"
-    else:
+    mode = detect_auth_mode(settings)
+
+    # Map deployment mode to auth_mode for API response
+    # This helps clients (like Astrolabe) determine which auth flow to use
+    if mode == AuthMode.OAUTH_SINGLE_AUDIENCE or mode == AuthMode.OAUTH_TOKEN_EXCHANGE:
         auth_mode = "oauth"
+    elif mode == AuthMode.MULTI_USER_BASIC:
+        auth_mode = "multi_user_basic"
+    elif mode == AuthMode.SINGLE_USER_BASIC:
+        auth_mode = "basic"
+    elif mode == AuthMode.SMITHERY_STATELESS:
+        auth_mode = "smithery"
+    else:
+        auth_mode = "unknown"
 
     response_data = {
         "version": __version__,
@@ -199,6 +383,10 @@ async def get_server_status(request: Request) -> JSONResponse:
         "management_api_version": "1.0",
     }
 
+    # Add app password support indicator for multi-user BasicAuth mode
+    if mode == AuthMode.MULTI_USER_BASIC:
+        response_data["supports_app_passwords"] = settings.enable_offline_access
+
     # Include OIDC configuration if in OAuth mode
     if auth_mode == "oauth":
         # Provide IdP discovery information for NC PHP app
@@ -334,11 +522,12 @@ async def get_user_session(request: Request) -> JSONResponse:
         )
 
     # Check if offline access is enabled
-    enable_offline_access = os.getenv("ENABLE_OFFLINE_ACCESS", "false").lower() in (
-        "true",
-        "1",
-        "yes",
-    )
+    # Use settings.enable_offline_access which handles both ENABLE_BACKGROUND_OPERATIONS (new)
+    # and ENABLE_OFFLINE_ACCESS (deprecated) environment variables
+    from nextcloud_mcp_server.config import get_settings
+
+    settings = get_settings()
+    enable_offline_access = settings.enable_offline_access
 
     if not enable_offline_access:
         # Offline access disabled - return minimal session info
@@ -479,6 +668,254 @@ async def revoke_user_access(request: Request) -> JSONResponse:
         )
 
 
+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
+    """
+    from nextcloud_mcp_server.config import get_settings
+
+    # 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 httpx.AsyncClient(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.
+    """
+    from nextcloud_mcp_server.config import get_settings
+
+    # 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 httpx.AsyncClient(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,
+        )
+
+
 async def get_installed_apps(request: Request) -> JSONResponse:
     """GET /api/v1/apps - Get list of installed Nextcloud apps.
 
@@ -500,8 +937,6 @@ async def get_installed_apps(request: Request) -> JSONResponse:
         )
 
     try:
-        import httpx
-
         # Get Bearer token from request
         token = extract_bearer_token(request)
         if not token:
@@ -572,8 +1007,6 @@ async def list_webhooks(request: Request) -> JSONResponse:
         )
 
     try:
-        import httpx
-
         from nextcloud_mcp_server.client.webhooks import WebhooksClient
 
         # Get Bearer token from request
@@ -639,8 +1072,6 @@ async def create_webhook(request: Request) -> JSONResponse:
         )
 
     try:
-        import httpx
-
         from nextcloud_mcp_server.client.webhooks import WebhooksClient
 
         # Parse request body
@@ -717,8 +1148,6 @@ async def delete_webhook(request: Request) -> JSONResponse:
         )
 
     try:
-        import httpx
-
         from nextcloud_mcp_server.client.webhooks import WebhooksClient
 
         # Get webhook_id from path parameter

nextcloud_mcp_server/auth/astrolabe_client.py

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

nextcloud_mcp_server/auth/browser_oauth_routes.py

@@ -8,6 +8,7 @@ import hashlib
 import logging
 import os
 import secrets
+import time
 from base64 import urlsafe_b64encode
 from urllib.parse import urlencode
 
@@ -301,25 +302,6 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
                 discovery = response.json()
                 token_endpoint = discovery["token_endpoint"]
 
-            # Rewrite token_endpoint from public URL to internal Docker URL
-            # Discovery document returns public URLs (e.g., http://localhost:8080/...)
-            # but server-side requests must use internal Docker network (e.g., http://app:80/...)
-            public_issuer = os.getenv("NEXTCLOUD_PUBLIC_ISSUER_URL")
-            if public_issuer:
-                from urllib.parse import urlparse as parse_url
-
-                internal_host = oauth_config["nextcloud_host"]
-                internal_parsed = parse_url(internal_host)
-                token_parsed = parse_url(token_endpoint)
-                public_parsed = parse_url(public_issuer)
-
-                if token_parsed.hostname == public_parsed.hostname:
-                    # Replace public URL with internal Docker URL
-                    token_endpoint = f"{internal_parsed.scheme}://{internal_parsed.netloc}{token_parsed.path}"
-                    logger.info(
-                        f"Rewrote token endpoint to internal URL: {token_endpoint}"
-                    )
-
             token_params = {
                 "grant_type": "authorization_code",
                 "code": code,
@@ -400,8 +382,6 @@ 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/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
@@ -155,7 +156,6 @@ 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

@@ -23,6 +23,7 @@ import hashlib
 import logging
 import os
 import secrets
+import time
 from base64 import urlsafe_b64encode
 from urllib.parse import urlencode
 
@@ -521,8 +522,6 @@ 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}")

nextcloud_mcp_server/auth/provisioning_decorator.py

@@ -9,6 +9,7 @@ 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
@@ -78,8 +79,6 @@ 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 +162,6 @@ 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
 
@@ -131,9 +130,12 @@ 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
+            from nextcloud_mcp_server.config import get_settings
+
+            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

@@ -28,6 +28,7 @@ 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
@@ -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 +1240,180 @@ 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 generate_encryption_key() -> str:
     """

nextcloud_mcp_server/auth/token_broker.py

@@ -168,37 +168,6 @@ 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 +376,7 @@ 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 +446,7 @@ 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/unified_verifier.py

@@ -117,6 +117,71 @@ 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 +251,78 @@ 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 +367,15 @@ 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 +388,22 @@ 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 +495,24 @@ 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 +537,13 @@ 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

@@ -9,6 +9,7 @@ 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
 
@@ -19,6 +20,7 @@ from starlette.requests import Request
 from starlette.responses import HTMLResponse, JSONResponse
 
 from nextcloud_mcp_server.client import NextcloudClient
+from nextcloud_mcp_server.config import get_settings
 
 logger = logging.getLogger(__name__)
 
@@ -105,9 +107,9 @@ 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 +128,8 @@ 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
 
-            settings = get_settings()
             qdrant_client = await get_qdrant_client()
 
             # Count documents in collection
@@ -385,8 +385,6 @@ 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 {
@@ -635,7 +633,9 @@ 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

@@ -15,6 +15,7 @@ import logging
 import time
 from pathlib import Path
 
+import anyio
 import numpy as np
 from jinja2 import Environment, FileSystemLoader
 from starlette.authentication import requires
@@ -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={

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/config.py

@@ -1,6 +1,7 @@
 import logging
 import logging.config
 import os
+import socket
 from dataclasses import dataclass
 from enum import Enum
 from typing import Any, Optional
@@ -163,6 +164,12 @@ def get_document_processor_config() -> dict[str, Any]:
 class Settings:
     """Application settings from environment variables."""
 
+    # Deployment mode (ADR-021: explicit mode selection)
+    # Optional: If not set, mode is auto-detected from other settings
+    # Valid values: single_user_basic, multi_user_basic, oauth_single_audience,
+    #               oauth_token_exchange, smithery
+    deployment_mode: Optional[str] = None
+
     # OAuth/OIDC settings
     oidc_discovery_url: Optional[str] = None
     oidc_client_id: Optional[str] = None
@@ -187,6 +194,11 @@ class Settings:
     enable_token_exchange: bool = False
     enable_offline_access: bool = False
 
+    # Multi-user BasicAuth pass-through mode (ADR-019 interim solution)
+    # When enabled, MCP server extracts BasicAuth credentials from request headers
+    # and passes them through to Nextcloud APIs (no storage, stateless)
+    enable_multi_user_basic_auth: bool = False
+
     # Token exchange cache settings
     token_exchange_cache_ttl: int = 300  # seconds (5 minutes default)
 
@@ -326,7 +338,6 @@ class Settings:
         Returns:
             Collection name string
         """
-        import socket
 
         # Use explicit override if user configured non-default value
         if self.qdrant_collection != "nextcloud_content":
@@ -345,6 +356,131 @@ 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.
@@ -352,7 +488,13 @@ 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"),
@@ -373,8 +515,10 @@ 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"
         ),
         # Token exchange cache settings
         token_exchange_cache_ttl=int(os.getenv("TOKEN_EXCHANGE_CACHE_TTL", "300")),
@@ -382,9 +526,7 @@ 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")

nextcloud_mcp_server/config_validators.py

@@ -0,0 +1,459 @@
+"""Configuration validation and mode detection for the MCP server.
+
+This module provides:
+- Mode detection based on configuration
+- Configuration validation with clear error messages
+- Single source of truth for deployment mode requirements
+
+See ADR-020 for detailed architecture and deployment mode documentation.
+"""
+
+import logging
+import os
+from dataclasses import dataclass
+from enum import Enum
+
+from nextcloud_mcp_server.config import Settings
+
+logger = logging.getLogger(__name__)
+
+
+class AuthMode(Enum):
+    """Authentication mode for the MCP server.
+
+    Determines how users authenticate and how the server accesses Nextcloud.
+    """
+
+    SINGLE_USER_BASIC = "single_user_basic"
+    MULTI_USER_BASIC = "multi_user_basic"
+    OAUTH_SINGLE_AUDIENCE = "oauth_single"
+    OAUTH_TOKEN_EXCHANGE = "oauth_exchange"
+    SMITHERY_STATELESS = "smithery"
+
+
+@dataclass
+class ModeRequirements:
+    """Requirements for a deployment mode.
+
+    Attributes:
+        required: Configuration variables that must be set
+        optional: Configuration variables that may be set
+        forbidden: Configuration variables that should not be set
+        conditional: Additional requirements based on feature flags
+                     Format: {feature_flag: [required_vars]}
+        description: Human-readable description of the mode
+    """
+
+    required: list[str]
+    optional: list[str]
+    forbidden: list[str]
+    conditional: dict[str, list[str]]
+    description: str
+
+
+# Mode requirements definition
+MODE_REQUIREMENTS: dict[AuthMode, ModeRequirements] = {
+    AuthMode.SINGLE_USER_BASIC: ModeRequirements(
+        required=["nextcloud_host", "nextcloud_username", "nextcloud_password"],
+        optional=[
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+            "document_chunk_size",
+            "document_chunk_overlap",
+        ],
+        forbidden=[
+            "enable_multi_user_basic_auth",
+            "enable_token_exchange",
+            "oidc_client_id",
+            "oidc_client_secret",
+        ],
+        conditional={
+            "vector_sync_enabled": [
+                # Either qdrant_url OR qdrant_location (checked in Settings.__post_init__)
+                # At least one embedding provider (ollama_base_url OR openai_api_key)
+            ],
+        },
+        description="Single-user deployment with BasicAuth credentials. "
+        "Suitable for personal Nextcloud instances and local development.",
+    ),
+    AuthMode.MULTI_USER_BASIC: ModeRequirements(
+        required=["nextcloud_host", "enable_multi_user_basic_auth"],
+        optional=[
+            # Background sync with app passwords (via Astrolabe)
+            "enable_offline_access",
+            "token_encryption_key",
+            "token_storage_db",
+            "oidc_client_id",
+            "oidc_client_secret",
+            # Vector sync
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+        ],
+        forbidden=[
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_token_exchange",
+        ],
+        conditional={
+            "enable_offline_access": [
+                # OAuth credentials validated separately (lines 397-406) with clearer error message
+                "token_encryption_key",
+                "token_storage_db",
+            ],
+            # Note: vector_sync_enabled (now ENABLE_SEMANTIC_SEARCH) automatically
+            # enables background operations in multi-user modes. No explicit
+            # enable_offline_access setting required.
+        },
+        description="Multi-user deployment with BasicAuth pass-through. "
+        "Users provide credentials in request headers. "
+        "Optional background sync using app passwords stored via Astrolabe.",
+    ),
+    AuthMode.OAUTH_SINGLE_AUDIENCE: ModeRequirements(
+        required=["nextcloud_host"],
+        optional=[
+            # OAuth credentials (uses DCR if not provided)
+            "oidc_client_id",
+            "oidc_client_secret",
+            "oidc_discovery_url",
+            # Offline access
+            "enable_offline_access",
+            "token_encryption_key",
+            "token_storage_db",
+            # Vector sync
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+            # Scopes
+            "nextcloud_oidc_scopes",
+        ],
+        forbidden=[
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_token_exchange",
+            "enable_multi_user_basic_auth",
+        ],
+        conditional={
+            "enable_offline_access": [
+                "token_encryption_key",
+                "token_storage_db",
+            ],
+            # Note: vector_sync_enabled (now ENABLE_SEMANTIC_SEARCH) automatically
+            # enables background operations in multi-user modes. No explicit
+            # enable_offline_access setting required.
+        },
+        description="OAuth multi-user deployment with single-audience tokens. "
+        "Tokens work for both MCP server and Nextcloud APIs (pass-through). "
+        "Uses Dynamic Client Registration if credentials not provided.",
+    ),
+    AuthMode.OAUTH_TOKEN_EXCHANGE: ModeRequirements(
+        required=["nextcloud_host", "enable_token_exchange"],
+        optional=[
+            # OAuth credentials
+            "oidc_client_id",
+            "oidc_client_secret",
+            "oidc_discovery_url",
+            # Token exchange settings
+            "token_exchange_cache_ttl",
+            # Offline access
+            "enable_offline_access",
+            "token_encryption_key",
+            "token_storage_db",
+            # Vector sync
+            "vector_sync_enabled",
+            "qdrant_url",
+            "qdrant_location",
+            "ollama_base_url",
+            "ollama_embedding_model",
+            "openai_api_key",
+            "openai_embedding_model",
+        ],
+        forbidden=[
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_multi_user_basic_auth",
+        ],
+        conditional={
+            "enable_offline_access": [
+                "token_encryption_key",
+                "token_storage_db",
+            ],
+            # Note: vector_sync_enabled (now ENABLE_SEMANTIC_SEARCH) automatically
+            # enables background operations in multi-user modes. No explicit
+            # enable_offline_access setting required.
+        },
+        description="OAuth multi-user deployment with token exchange (RFC 8693). "
+        "MCP tokens are separate from Nextcloud tokens. "
+        "Server exchanges MCP token for Nextcloud token on each request.",
+    ),
+    AuthMode.SMITHERY_STATELESS: ModeRequirements(
+        required=[],  # All config from session URL params
+        optional=[],
+        forbidden=[
+            "nextcloud_host",
+            "nextcloud_username",
+            "nextcloud_password",
+            "enable_multi_user_basic_auth",
+            "enable_token_exchange",
+            "enable_offline_access",
+            "vector_sync_enabled",
+            "oidc_client_id",
+            "oidc_client_secret",
+        ],
+        conditional={},
+        description="Stateless multi-tenant deployment for Smithery platform. "
+        "Configuration comes from session URL parameters. "
+        "No persistent storage, no OAuth, no vector sync.",
+    ),
+}
+
+
+def detect_auth_mode(settings: Settings) -> AuthMode:
+    """Detect authentication mode from configuration.
+
+    Mode detection priority (ADR-021):
+    0. Explicit MCP_DEPLOYMENT_MODE (if set) - NEW in ADR-021
+    1. Smithery (explicit flag)
+    2. Token exchange (most specific OAuth mode)
+    3. Multi-user BasicAuth
+    4. Single-user BasicAuth
+    5. OAuth single-audience (default OAuth mode)
+
+    Args:
+        settings: Application settings
+
+    Returns:
+        Detected AuthMode
+
+    Raises:
+        ValueError: If explicit deployment_mode is invalid or conflicts with detected mode
+    """
+
+    logger = logging.getLogger(__name__)
+
+    # ADR-021: Check for explicit deployment mode first
+    if settings.deployment_mode:
+        mode_str = settings.deployment_mode.lower().strip()
+
+        # Map string to AuthMode enum
+        mode_map = {
+            "single_user_basic": AuthMode.SINGLE_USER_BASIC,
+            "multi_user_basic": AuthMode.MULTI_USER_BASIC,
+            "oauth_single_audience": AuthMode.OAUTH_SINGLE_AUDIENCE,
+            "oauth_token_exchange": AuthMode.OAUTH_TOKEN_EXCHANGE,
+            "smithery": AuthMode.SMITHERY_STATELESS,
+        }
+
+        if mode_str not in mode_map:
+            valid_modes = ", ".join(mode_map.keys())
+            raise ValueError(
+                f"Invalid MCP_DEPLOYMENT_MODE: '{settings.deployment_mode}'. "
+                f"Valid values: {valid_modes}"
+            )
+
+        explicit_mode = mode_map[mode_str]
+        logger.info(f"Using explicit deployment mode: {explicit_mode.value}")
+        return explicit_mode
+
+    # Auto-detection (existing behavior)
+    # Check for Smithery mode (explicit environment variable)
+    # Note: This checks the environment directly, not settings
+    # because Smithery mode has no settings-based config
+    if os.getenv("SMITHERY_DEPLOYMENT", "false").lower() == "true":
+        return AuthMode.SMITHERY_STATELESS
+
+    # Check for token exchange (most specific OAuth mode)
+    if settings.enable_token_exchange:
+        return AuthMode.OAUTH_TOKEN_EXCHANGE
+
+    # Check for multi-user BasicAuth
+    if settings.enable_multi_user_basic_auth:
+        return AuthMode.MULTI_USER_BASIC
+
+    # Check for single-user BasicAuth (explicit credentials)
+    if settings.nextcloud_username and settings.nextcloud_password:
+        return AuthMode.SINGLE_USER_BASIC
+
+    # Default: OAuth single-audience mode
+    # This is the safest multi-user mode (no credential storage)
+    return AuthMode.OAUTH_SINGLE_AUDIENCE
+
+
+def validate_configuration(settings: Settings) -> tuple[AuthMode, list[str]]:
+    """Validate configuration for detected mode.
+
+    Args:
+        settings: Application settings
+
+    Returns:
+        Tuple of (detected_mode, list_of_errors)
+        Empty list means valid configuration.
+    """
+    mode = detect_auth_mode(settings)
+    requirements = MODE_REQUIREMENTS[mode]
+    errors: list[str] = []
+
+    logger.debug(f"Validating configuration for mode: {mode.value}")
+
+    # Check required variables
+    for var in requirements.required:
+        value = getattr(settings, var, None)
+        if value is None or (isinstance(value, str) and not value.strip()):
+            errors.append(
+                f"[{mode.value}] Missing required configuration: {var.upper()}"
+            )
+
+    # Check forbidden variables
+    for var in requirements.forbidden:
+        value = getattr(settings, var, None)
+        # For bools, check if True (forbidden means must be False/unset)
+        # For strings, check if non-empty
+        is_set = False
+        if isinstance(value, bool):
+            is_set = value is True
+        elif isinstance(value, str):
+            is_set = bool(value.strip())
+        elif value is not None:
+            is_set = True
+
+        if is_set:
+            errors.append(
+                f"[{mode.value}] Forbidden configuration: {var.upper()} "
+                f"should not be set in this mode"
+            )
+
+    # Check conditional requirements
+    for condition, required_vars in requirements.conditional.items():
+        # Check if the condition is enabled
+        condition_value = getattr(settings, condition, None)
+        is_enabled = False
+
+        if isinstance(condition_value, bool):
+            is_enabled = condition_value is True
+        elif isinstance(condition_value, str):
+            is_enabled = bool(condition_value.strip())
+        elif condition_value is not None:
+            is_enabled = True
+
+        if is_enabled:
+            # Check that all required vars for this condition are set
+            for var in required_vars:
+                value = getattr(settings, var, None)
+
+                # For boolean requirements, check that they are True (not just set)
+                if hasattr(Settings, var):
+                    field_type = type(getattr(Settings(), var, None))
+                    if field_type is bool:
+                        if value is not True:
+                            errors.append(
+                                f"[{mode.value}] {var.upper()} must be enabled when "
+                                f"{condition.upper()} is enabled"
+                            )
+                        continue
+
+                # For non-boolean requirements, check that they are set
+                if value is None or (isinstance(value, str) and not value.strip()):
+                    errors.append(
+                        f"[{mode.value}] {var.upper()} is required when "
+                        f"{condition.upper()} is enabled"
+                    )
+
+    # Special validations for specific modes
+    if mode == AuthMode.SINGLE_USER_BASIC:
+        # Validate that NEXTCLOUD_HOST doesn't have trailing slash
+        if settings.nextcloud_host and settings.nextcloud_host.endswith("/"):
+            errors.append(
+                f"[{mode.value}] NEXTCLOUD_HOST should not have trailing slash: "
+                f"{settings.nextcloud_host}"
+            )
+
+    if mode in [
+        AuthMode.OAUTH_SINGLE_AUDIENCE,
+        AuthMode.OAUTH_TOKEN_EXCHANGE,
+    ]:
+        # If OAuth credentials not provided, DCR must be available
+        # (This is a runtime check, not a config check, so we just warn)
+        if not settings.oidc_client_id or not settings.oidc_client_secret:
+            logger.info(
+                f"[{mode.value}] OAuth credentials not configured. "
+                "Will attempt Dynamic Client Registration (DCR) at startup."
+            )
+
+    if mode == AuthMode.MULTI_USER_BASIC:
+        # If background operations enabled, check for OAuth credentials (for app password retrieval)
+        # Allow DCR as fallback, just like OAuth modes
+        if settings.enable_offline_access:
+            if not settings.oidc_client_id or not settings.oidc_client_secret:
+                logger.info(
+                    f"[{mode.value}] OAuth credentials not configured. "
+                    "Will attempt Dynamic Client Registration (DCR) at startup "
+                    "(required for app password retrieval via Astrolabe)."
+                )
+
+        # Note: Vector sync no longer requires explicit ENABLE_OFFLINE_ACCESS setting
+        # ENABLE_SEMANTIC_SEARCH (formerly VECTOR_SYNC_ENABLED) automatically enables
+        # background operations in multi-user modes via smart dependency resolution
+        # in config.py
+
+    # Note: Embedding provider validation removed - Simple provider is always
+    # available as fallback (ADR-015). Users can optionally configure Ollama or OpenAI
+    # for better quality embeddings.
+
+    return mode, errors
+
+
+def get_mode_summary(mode: AuthMode) -> str:
+    """Get human-readable summary of a deployment mode.
+
+    Args:
+        mode: Deployment mode
+
+    Returns:
+        Multi-line string describing the mode
+    """
+    requirements = MODE_REQUIREMENTS[mode]
+
+    summary_lines = [
+        f"Mode: {mode.value}",
+        f"Description: {requirements.description}",
+        "",
+        "Required configuration:",
+    ]
+
+    if requirements.required:
+        for var in requirements.required:
+            summary_lines.append(f"  - {var.upper()}")
+    else:
+        summary_lines.append("  (none - configured via session)")
+
+    summary_lines.append("")
+    summary_lines.append("Optional configuration:")
+
+    if requirements.optional:
+        for var in requirements.optional:
+            summary_lines.append(f"  - {var.upper()}")
+    else:
+        summary_lines.append("  (none)")
+
+    if requirements.conditional:
+        summary_lines.append("")
+        summary_lines.append("Conditional requirements:")
+        for condition, vars in requirements.conditional.items():
+            summary_lines.append(f"  When {condition.upper()} is enabled:")
+            for var in vars:
+                summary_lines.append(f"    - {var.upper()}")
+
+    return "\n".join(summary_lines)

nextcloud_mcp_server/context.py

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

nextcloud_mcp_server/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/migrations.py

@@ -6,6 +6,7 @@ provides CLI integration.
 """
 
 import logging
+import sqlite3
 from pathlib import Path
 
 from alembic.config import Config
@@ -98,7 +99,6 @@ 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/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,
@@ -423,8 +425,6 @@ 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
 

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

@@ -7,6 +7,9 @@ position markers for better visualization and understanding of search results.
 import logging
 from dataclasses import dataclass
 
+import pymupdf
+import pymupdf4llm
+
 from nextcloud_mcp_server.client import NextcloudClient
 
 logger = logging.getLogger(__name__)
@@ -549,8 +552,6 @@ 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")

nextcloud_mcp_server/search/pdf_highlighter.py

@@ -10,6 +10,9 @@ varies between indexing and rendering.
 
 import logging
 import re
+import shutil
+import tempfile
+from pathlib import Path
 from typing import Optional
 
 import pymupdf
@@ -77,8 +80,6 @@ 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 +111,6 @@ class PDFHighlighter:
         full_text = "".join(text_parts)
 
         # Clean up temp directory and extracted images
-        import shutil
 
         try:
             shutil.rmtree(temp_dir)
@@ -590,8 +590,6 @@ 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:

nextcloud_mcp_server/server/deck.py

@@ -637,7 +637,9 @@ 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 +694,9 @@ 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

@@ -12,6 +12,7 @@ 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
@@ -53,8 +54,6 @@ 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}")
@@ -101,6 +100,9 @@ class ProvisioningStatus(BaseModel):
     provisioned_at: Optional[str] = Field(
         None, description="ISO timestamp when provisioned"
     )
+    credential_type: Optional[str] = Field(
+        None, description="Type of credential ('refresh_token' or 'app_password')"
+    )
     client_id: Optional[str] = Field(
         None, description="Client ID that initiated the original Flow 1"
     )
@@ -114,8 +116,8 @@ class ProvisioningResult(BaseModel):
     """Result of provisioning attempt."""
 
     success: bool = Field(description="Whether provisioning was initiated")
-    authorization_url: Optional[str] = Field(
-        None, description="URL for user to complete OAuth authorization"
+    provisioning_url: Optional[str] = Field(
+        None, description="URL to Astrolabe settings for provisioning background sync"
     )
     message: str = Field(description="Status message for the user")
     already_provisioned: bool = Field(
@@ -143,8 +145,9 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
     """
     Check the provisioning status for Nextcloud access.
 
-    This checks whether the user has completed Flow 2 to provision
-    offline access to Nextcloud resources.
+    Checks for both credential types:
+    1. App password from Astrolabe (works today)
+    2. OAuth refresh token from storage (for future)
 
     Args:
         mcp: MCP context
@@ -153,6 +156,37 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
     Returns:
         ProvisioningStatus with current provisioning state
     """
+    from datetime import datetime, timezone
+
+    from nextcloud_mcp_server.auth.astrolabe_client import AstrolabeClient
+    from nextcloud_mcp_server.config import get_settings
+
+    settings = get_settings()
+
+    # Check for app password first (interim solution)
+    if settings.oidc_client_id and settings.oidc_client_secret:
+        try:
+            astrolabe = AstrolabeClient(
+                nextcloud_host=settings.nextcloud_host or "",
+                client_id=settings.oidc_client_id,
+                client_secret=settings.oidc_client_secret,
+            )
+            status = await astrolabe.get_background_sync_status(user_id)
+
+            if status.get("has_access"):
+                logger.info(
+                    f"  get_provisioning_status: ✓ App password FOUND for user_id={user_id}"
+                )
+                provisioned_at_str = status.get("provisioned_at")
+                return ProvisioningStatus(
+                    is_provisioned=True,
+                    provisioned_at=provisioned_at_str,
+                    credential_type="app_password",
+                )
+        except Exception as e:
+            logger.debug(f"  App password check failed for {user_id}: {e}")
+
+    # Check for OAuth refresh token (fallback)
     logger.info(
         f"  get_provisioning_status: Looking up refresh token for user_id={user_id}"
     )
@@ -163,7 +197,7 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
 
     if not token_data:
         logger.info(
-            f"  get_provisioning_status: ✗ No refresh token found for user_id={user_id}"
+            f"  get_provisioning_status: ✗ No credentials found for user_id={user_id}"
         )
         return ProvisioningStatus(is_provisioned=False)
 
@@ -178,14 +212,13 @@ async def get_provisioning_status(ctx: Context, user_id: str) -> ProvisioningSta
     # Convert timestamp to ISO format if present
     provisioned_at_str = None
     if token_data.get("provisioned_at"):
-        from datetime import datetime, timezone
-
         dt = datetime.fromtimestamp(token_data["provisioned_at"], tz=timezone.utc)
         provisioned_at_str = dt.isoformat()
 
     return ProvisioningStatus(
         is_provisioned=True,
         provisioned_at=provisioned_at_str,
+        credential_type="refresh_token",
         client_id=token_data.get("provisioning_client_id"),
         scopes=token_data.get("scopes"),
         flow_type=token_data.get("flow_type", "hybrid"),
@@ -239,36 +272,22 @@ async def provision_nextcloud_access(
     """
     MCP Tool: Provision offline access to Nextcloud resources.
 
-    This tool initiates Flow 2 of the Progressive Consent architecture,
-    allowing the MCP server to obtain delegated access to Nextcloud APIs.
-
-    The user must complete the OAuth flow in their browser to grant access.
+    Returns URL to Astrolabe settings page where users can provision background
+    sync access using either:
+    - App password (works today, interim solution)
+    - OAuth refresh token (future, when Nextcloud supports OAuth for app APIs)
 
     Args:
         ctx: MCP context with user's Flow 1 token
         user_id: Optional user identifier (extracted from token if not provided)
 
     Returns:
-        ProvisioningResult with authorization URL or status
+        ProvisioningResult with Astrolabe settings URL or status
     """
     try:
         # Extract user ID from the MCP access token (Flow 1 token)
         if not user_id:
-            # Get the authorization token from context
-            if hasattr(ctx, "authorization") and ctx.authorization:
-                token = ctx.authorization.token  # type: ignore
-                # Decode token to get user info
-                try:
-                    import jwt
-
-                    payload = jwt.decode(token, options={"verify_signature": False})
-                    user_id = payload.get("sub", "unknown")
-                    logger.info(f"Extracted user_id from Flow 1 token: {user_id}")
-                except Exception as e:
-                    logger.warning(f"Failed to decode token: {e}")
-                    user_id = "default_user"
-            else:
-                user_id = "default_user"
+            user_id = await extract_user_id_from_token(ctx)
 
         # Check if already provisioned
         status = await get_provisioning_status(ctx, user_id)
@@ -277,101 +296,40 @@ async def provision_nextcloud_access(
                 success=True,
                 already_provisioned=True,
                 message=(
-                    f"Nextcloud access is already provisioned (since {status.provisioned_at}). "
+                    f"Nextcloud access is already provisioned (credential_type={status.credential_type}, "
+                    f"since {status.provisioned_at}). "
                     "Use 'revoke_nextcloud_access' if you want to re-provision."
                 ),
             )
 
-        # 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)
+        from nextcloud_mcp_server.config import get_settings
+
+        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."
                 ),
             )
 
-        # Get MCP server's OAuth client credentials
-        # Try environment variable first, then fall back to DCR client_id
-        server_client_id = os.getenv("MCP_SERVER_CLIENT_ID")
-        if not server_client_id:
-            # Try to get from lifespan context (DCR)
-            lifespan_ctx = ctx.request_context.lifespan_context
-            if hasattr(lifespan_ctx, "server_client_id"):
-                server_client_id = lifespan_ctx.server_client_id
-
-        if not server_client_id:
-            return ProvisioningResult(
-                success=False,
-                message=(
-                    "MCP server OAuth client not configured. "
-                    "Set MCP_SERVER_CLIENT_ID environment variable or use Dynamic Client Registration."
-                ),
-            )
-
-        # Generate OAuth URL for Flow 2
-        oidc_discovery_url = os.getenv(
-            "OIDC_DISCOVERY_URL",
-            f"{os.getenv('NEXTCLOUD_HOST')}/.well-known/openid-configuration",
-        )
-
-        # Generate secure state for CSRF protection
-        state = secrets.token_urlsafe(32)
-
-        # Store state in session for validation on callback
-        storage = RefreshTokenStorage.from_env()
-        await storage.initialize()
-
-        # Create OAuth session for Flow 2
-        session_id = f"flow2_{user_id}_{secrets.token_hex(8)}"
-        redirect_uri = f"{os.getenv('NEXTCLOUD_MCP_SERVER_URL', 'http://localhost:8000')}/oauth/callback"
-
-        await storage.store_oauth_session(
-            session_id=session_id,
-            client_redirect_uri="",  # No client redirect for Flow 2
-            state=state,
-            flow_type="flow2",
-            is_provisioning=True,
-            ttl_seconds=600,  # 10 minute TTL
-        )
-
-        # Define scopes for Nextcloud access
-        scopes = [
-            "openid",
-            "profile",
-            "email",
-            "offline_access",  # Critical for background operations
-            "notes:read",
-            "notes:write",
-            "calendar:read",
-            "calendar:write",
-            "contacts:read",
-            "contacts:write",
-            "files:read",
-            "files:write",
-        ]
-
-        # Generate authorization URL
-        auth_url = generate_oauth_url_for_flow2(
-            oidc_discovery_url=oidc_discovery_url,
-            server_client_id=server_client_id,
-            redirect_uri=redirect_uri,
-            state=state,
-            scopes=scopes,
-        )
+        # Return Astrolabe settings URL for background sync provisioning
+        nextcloud_host = os.getenv("NEXTCLOUD_HOST", "http://localhost:8080")
+        astrolabe_url = f"{nextcloud_host}/settings/user/astrolabe#background-sync"
 
         return ProvisioningResult(
             success=True,
-            authorization_url=auth_url,
+            provisioning_url=astrolabe_url,
             message=(
-                "Please visit the authorization URL to grant the MCP server "
-                "offline access to your Nextcloud resources. This is a one-time "
-                "setup that allows the server to access Nextcloud on your behalf "
-                "even when you're not actively connected."
+                "Visit Astrolabe settings to provision background sync access.\n\n"
+                "You can choose either:\n"
+                "- App password (works today, recommended for now)\n"
+                "- OAuth refresh token (future, when Nextcloud fully supports OAuth)\n\n"
+                "After provisioning, background sync will enable the MCP server to "
+                "access Nextcloud resources even when you're not actively connected."
             ),
         )
 
@@ -530,13 +488,14 @@ 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)
+        from nextcloud_mcp_server.config import get_settings
+
+        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

@@ -656,14 +656,12 @@ 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"
-        )
+        # Check if vector sync is enabled (supports both old and new env var names)
+        from nextcloud_mcp_server.config import get_settings
 
-        if not vector_sync_enabled:
+        settings = get_settings()
+        if not settings.vector_sync_enabled:
             return VectorSyncStatusResponse(
                 indexed_count=0,
                 pending_count=0,

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/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

@@ -1,10 +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
+
+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
@@ -18,6 +31,7 @@ from anyio.streams.memory import (
     MemoryObjectReceiveStream,
     MemoryObjectSendStream,
 )
+from httpx import BasicAuth
 
 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import get_settings
@@ -53,12 +67,61 @@ 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
+    """
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+
+    # 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.
+
+    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
@@ -66,15 +129,19 @@ 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
     """
     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,
@@ -82,30 +149,66 @@ 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()
 
     task_status.started()
@@ -113,8 +216,10 @@ async def user_scanner_task(
     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(
@@ -125,12 +230,14 @@ async def user_scanner_task(
 
         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 Exception as e:
-            logger.error(f"[OAuth] Scanner error for {user_id}: {e}", exc_info=True)
+            logger.error(
+                f"[{mode_label}] Scanner error for {user_id}: {e}", exc_info=True
+            )
 
         finally:
             if nc_client:
@@ -143,33 +250,36 @@ 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():
@@ -180,9 +290,12 @@ 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
@@ -192,13 +305,13 @@ 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
@@ -206,18 +319,24 @@ 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(
@@ -226,9 +345,10 @@ 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.
 
@@ -244,6 +364,7 @@ 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
@@ -256,48 +377,60 @@ 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(
@@ -316,24 +449,27 @@ 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:
@@ -344,9 +480,9 @@ 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/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
@@ -585,8 +586,6 @@ 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

nextcloud_mcp_server/vector/scanner.py

@@ -5,6 +5,7 @@ Periodically scans enabled users' content and queues changed documents for proce
 
 import logging
 import os
+import random
 import time
 from dataclasses import dataclass
 
@@ -167,7 +168,6 @@ async def scan_user_documents(
         nc_client: Authenticated Nextcloud client
         initial_sync: If True, send all documents (first-time sync)
     """
-    import random
 
     scan_id = random.randint(1000, 9999)
     logger.info(

pyproject.toml

@@ -1,6 +1,6 @@
 [project]
 name = "nextcloud-mcp-server"
-version = "0.56.2"
+version = "0.61.3"
 description = "Model Context Protocol (MCP) server for Nextcloud integration - enables AI assistants to interact with Nextcloud data"
 authors = [
     {name = "Chris Coutinho", email = "chris@coutinho.io"}
@@ -64,7 +64,7 @@ Changelog = "https://github.com/cbcoutinho/nextcloud-mcp-server/blob/master/CHAN
 
 [tool.pytest.ini_options]
 anyio_mode = "auto"
-addopts = "-p no:asyncio -x"  # Disable pytest-asyncio plugin, use only anyio
+addopts = "-p no:asyncio"  # Disable pytest-asyncio plugin, use only anyio
 log_cli = 1
 log_cli_level = "ERROR"
 log_level = "ERROR"

scripts/bump-astrolabe.sh

@@ -58,6 +58,15 @@ fi
 # Run commitizen bump and capture output
 if ! output=$($CZ_CMD 2>&1); then
     cd ../..
+
+    # Check if this is the expected "no commits to bump" case
+    if echo "$output" | grep -q "\[NO_COMMITS_TO_BUMP\]"; then
+        echo "ℹ️  No commits eligible for version bump" >&2
+        echo "$output" >&2
+        exit 0
+    fi
+
+    # Otherwise, this is an actual error
     echo "❌ Error: Version bump failed" >&2
     echo "$output" >&2
     echo "" >&2

scripts/bump-helm.sh

@@ -53,6 +53,15 @@ fi
 # Run commitizen bump and capture output
 if ! output=$($CZ_CMD 2>&1); then
     cd ../..
+
+    # Check if this is the expected "no commits to bump" case
+    if echo "$output" | grep -q "\[NO_COMMITS_TO_BUMP\]"; then
+        echo "ℹ️  No commits eligible for version bump" >&2
+        echo "$output" >&2
+        exit 0
+    fi
+
+    # Otherwise, this is an actual error
     echo "❌ Error: Version bump failed" >&2
     echo "$output" >&2
     echo "" >&2

scripts/bump-mcp.sh

@@ -44,6 +44,14 @@ fi
 
 # Run commitizen bump and capture output
 if ! output=$($CZ_CMD 2>&1); then
+    # Check if this is the expected "no commits to bump" case
+    if echo "$output" | grep -q "\[NO_COMMITS_TO_BUMP\]"; then
+        echo "ℹ️  No commits eligible for version bump" >&2
+        echo "$output" >&2
+        exit 0
+    fi
+
+    # Otherwise, this is an actual error
     echo "❌ Error: Version bump failed" >&2
     echo "$output" >&2
     echo "" >&2

tests/client/conftest.py

@@ -1,3 +1,5 @@
+import json
+
 import httpx
 
 # ============================================================================
@@ -22,14 +24,13 @@ def create_mock_response(
     Returns:
         Mock httpx.Response object
     """
-    import json as json_module
 
     if headers is None:
         headers = {}
 
     # If json_data is provided, serialize it to content
     if json_data is not None:
-        content = json_module.dumps(json_data).encode("utf-8")
+        content = json.dumps(json_data).encode("utf-8")
         headers.setdefault("content-type", "application/json")
 
     if content is None:

tests/client/deck/test_deck_update_card_api.py

@@ -0,0 +1,194 @@
+"""
+Integration tests for DeckClient.update_card API behavior.
+
+These tests define the EXPECTED behavior for partial card updates:
+- Only fields explicitly passed should be modified
+- All other fields should be preserved unchanged
+
+Related issues:
+- nextcloud-mcp-server #452: DeckClient.update_card partial update bugs
+- deck #3127: REST API Docs: missing parameter in "update cards"
+- deck #4106: Provide a working example of API usage to update a cards details
+"""
+
+import pytest
+
+pytestmark = [pytest.mark.integration]
+
+
+@pytest.fixture
+async def deck_test_card(nc_client):
+    """Create a board, stack, and card for testing, cleanup after."""
+    board = await nc_client.deck.create_board("Test Update Card API", "FF0000")
+    stack = await nc_client.deck.create_stack(board.id, "Test Stack", 1)
+    card = await nc_client.deck.create_card(
+        board.id,
+        stack.id,
+        "Original Title",
+        type="plain",
+        description="Original description",
+    )
+
+    yield {
+        "board_id": board.id,
+        "stack_id": stack.id,
+        "card_id": card.id,
+        "card": card,
+    }
+
+    # Cleanup
+    await nc_client.deck.delete_board(board.id)
+
+
+class TestDeckClientUpdateCard:
+    """
+    Test DeckClient.update_card() partial update behavior.
+
+    Expected: Only explicitly provided fields are updated, all others preserved.
+    """
+
+    async def test_update_title_only_preserves_description(
+        self, nc_client, deck_test_card
+    ):
+        """Updating only the title should preserve the description."""
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            title="New Title",
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.title == "New Title"
+        assert updated.description == "Original description"
+
+    async def test_update_description_only(self, nc_client, deck_test_card):
+        """Updating only the description should work and preserve other fields."""
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            description="New description only",
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.title == "Original Title"
+        assert updated.description == "New description only"
+
+    async def test_update_title_and_description(self, nc_client, deck_test_card):
+        """Updating title and description together should work."""
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            title="New Title",
+            description="New description",
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.title == "New Title"
+        assert updated.description == "New description"
+
+    async def test_update_duedate_only(self, nc_client, deck_test_card):
+        """Updating only the duedate should work and preserve other fields."""
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            duedate="2025-12-31T23:59:59+00:00",
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.title == "Original Title"
+        assert updated.description == "Original description"
+        assert updated.duedate is not None
+
+    async def test_update_archived_only(self, nc_client, deck_test_card):
+        """Updating only the archived status should work and preserve other fields."""
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            archived=True,
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.title == "Original Title"
+        assert updated.description == "Original description"
+        assert updated.archived is True
+
+    async def test_update_order_only(self, nc_client, deck_test_card):
+        """Updating only the order should work and preserve other fields."""
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            order=99,
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.title == "Original Title"
+        assert updated.description == "Original description"
+        assert updated.order == 99
+
+    async def test_update_preserves_type(self, nc_client, deck_test_card):
+        """Type should be preserved when not explicitly changed."""
+        original = deck_test_card["card"]
+
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            title="Changed Title",
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.type == original.type
+        assert updated.description == "Original description"
+
+    async def test_update_preserves_owner(self, nc_client, deck_test_card):
+        """Owner should be preserved when not explicitly changed."""
+        original = deck_test_card["card"]
+
+        await nc_client.deck.update_card(
+            board_id=deck_test_card["board_id"],
+            stack_id=deck_test_card["stack_id"],
+            card_id=deck_test_card["card_id"],
+            title="Changed Title",
+        )
+
+        updated = await nc_client.deck.get_card(
+            deck_test_card["board_id"],
+            deck_test_card["stack_id"],
+            deck_test_card["card_id"],
+        )
+        assert updated.owner == original.owner
+        assert updated.description == "Original description"

tests/conftest.py

@@ -1,7 +1,17 @@
+import base64
+import hashlib
+import json
 import logging
 import os
+import re
+import secrets
+import subprocess
+import threading
+import time
 import uuid
+from http.server import BaseHTTPRequestHandler, HTTPServer
 from typing import Any, AsyncGenerator
+from urllib.parse import parse_qs, quote, urlparse
 
 import anyio
 import httpx
@@ -114,6 +124,7 @@ async def create_mcp_client_session(
     client_name: str = "MCP",
     elicitation_callback: Any = None,
     sampling_callback: Any = None,
+    headers: dict[str, str] | None = None,
 ) -> AsyncGenerator[ClientSession, Any]:
     """
     Factory function to create an MCP client session with proper lifecycle management.
@@ -135,6 +146,8 @@ async def create_mcp_client_session(
             Should match signature: async def callback(context: RequestContext, params: ElicitRequestParams) -> ElicitResult | ErrorData
         sampling_callback: Optional callback for handling sampling (LLM generation) requests.
             Should match signature: async def callback(context: RequestContext, params: CreateMessageRequestParams) -> CreateMessageResult | ErrorData
+        headers: Optional custom headers (e.g., for BasicAuth). If both headers and token are provided,
+            custom headers take precedence.
 
     Yields:
         Initialized MCP ClientSession
@@ -147,8 +160,9 @@ async def create_mcp_client_session(
     """
     logger.info(f"Creating Streamable HTTP client for {client_name}")
 
-    # Prepare headers with OAuth token if provided
-    headers = {"Authorization": f"Bearer {token}"} if token else None
+    # Prepare headers - custom headers take precedence over token-based auth
+    if headers is None:
+        headers = {"Authorization": f"Bearer {token}"} if token else None
 
     # Use native async with - Python ensures LIFO cleanup
     # Cleanup order will be: ClientSession.__aexit__ -> streamablehttp_client.__aexit__
@@ -240,6 +254,31 @@ async def nc_mcp_oauth_client(
         yield session
 
 
+@pytest.fixture(scope="session")
+async def nc_mcp_basic_auth_client(
+    anyio_backend,
+) -> AsyncGenerator[ClientSession, Any]:
+    """
+    Fixture to create an MCP client session with BasicAuth credentials.
+    Connects to the multi-user BasicAuth MCP server on port 8003 with ENABLE_MULTI_USER_BASIC_AUTH=true.
+
+    Uses BasicAuth credentials for multi-user pass-through mode (ADR-020).
+    Credentials are passed in Authorization header and forwarded to Nextcloud APIs.
+
+    Uses anyio pytest plugin for proper async fixture handling.
+    """
+
+    credentials = base64.b64encode(b"admin:admin").decode("utf-8")
+    auth_header = f"Basic {credentials}"
+
+    async for session in create_mcp_client_session(
+        url="http://localhost:8003/mcp",
+        headers={"Authorization": auth_header},
+        client_name="BasicAuth MCP (Multi-User)",
+    ):
+        yield session
+
+
 @pytest.fixture(scope="session")
 async def nc_mcp_oauth_jwt_client(
     anyio_backend,
@@ -312,7 +351,6 @@ async def nc_mcp_oauth_client_with_elicitation(
         logger.info(f"  Schema: {params.schema}")
 
         # Extract OAuth URL from elicitation message
-        import re
 
         url_pattern = r"https?://[^\s]+"
         urls = re.findall(url_pattern, params.message)
@@ -1078,10 +1116,6 @@ def oauth_callback_server():
     # "OAuth tests with browser automation not supported in GitHub Actions CI"
     # )
 
-    import threading
-    from http.server import BaseHTTPRequestHandler, HTTPServer
-    from urllib.parse import parse_qs, urlparse
-
     # Use a dict to store auth codes keyed by state parameter
     # This allows multiple concurrent OAuth flows
     auth_states = {}
@@ -1728,9 +1762,6 @@ async def playwright_oauth_token(
     - Browser fixture provided by pytest-playwright-asyncio
     - See: https://playwright.dev/python/docs/test-runners
     """
-    import secrets
-    import time
-    from urllib.parse import quote
 
     nextcloud_host = os.getenv("NEXTCLOUD_HOST")
     username = os.getenv("NEXTCLOUD_USERNAME")
@@ -2017,9 +2048,6 @@ async def _get_oauth_token_with_scopes(
     Returns:
         OAuth access token string with requested scopes
     """
-    import secrets
-    import time
-    from urllib.parse import quote
 
     nextcloud_host = os.getenv("NEXTCLOUD_HOST")
     username = os.getenv("NEXTCLOUD_USERNAME")
@@ -2290,7 +2318,10 @@ async def test_users_setup(anyio_backend, nc_client: NextcloudClient):
         },
     }
 
-    logger.info("Creating test users for multi-user OAuth testing...")
+    logger.info("=" * 60)
+    logger.info("EXECUTING test_users_setup FIXTURE (session-scoped)")
+    logger.info(f"Creating test users: {list(test_user_configs.keys())}")
+    logger.info("=" * 60)
     created_users = []
 
     try:
@@ -2384,9 +2415,6 @@ async def _get_oauth_token_for_user(
     Returns:
         OAuth access token string
     """
-    import secrets
-    import time
-    from urllib.parse import quote
 
     nextcloud_host = os.getenv("NEXTCLOUD_HOST")
 
@@ -2527,7 +2555,6 @@ async def all_oauth_tokens(
     Now uses the real callback server with state parameters for reliable
     concurrent token acquisition without race conditions.
     """
-    import time
 
     # Get auth_states dict from callback server
     auth_states, callback_url = oauth_callback_server
@@ -2678,7 +2705,6 @@ async def test_user(nc_client: NextcloudClient):
             user_config = test_user
             await nc_client.users.create_user(**user_config)
     """
-    import uuid
 
     # Generate unique user ID to avoid conflicts
     userid = f"testuser_{uuid.uuid4().hex[:8]}"
@@ -2714,7 +2740,6 @@ async def test_group(nc_client: NextcloudClient):
 
     Returns the group ID.
     """
-    import uuid
 
     # Generate unique group ID to avoid conflicts
     groupid = f"testgroup_{uuid.uuid4().hex[:8]}"
@@ -2849,11 +2874,6 @@ async def _get_keycloak_oauth_token(
     Returns:
         OAuth access token string from Keycloak
     """
-    import base64
-    import hashlib
-    import secrets
-    import time
-    from urllib.parse import quote
 
     # Get auth_states dict from callback server
     auth_states, _ = oauth_callback_server
@@ -3187,3 +3207,238 @@ async def nc_mcp_keycloak_client_no_custom_scopes(
         client_name="Keycloak No Custom Scopes MCP",
     ):
         yield session
+
+
+# ========================================================================
+# Astrolabe Dynamic Configuration Fixtures
+# ========================================================================
+
+
+@pytest.fixture(scope="session")
+async def configure_astrolabe_for_mcp_server(nc_client):
+    """Configure Astrolabe app to connect to a specific MCP server.
+
+    This fixture dynamically configures the Astrolabe app's MCP server settings
+    and OAuth client, allowing tests to verify integration with different MCP
+    server deployments (mcp-oauth, mcp-keycloak, mcp-multi-user-basic, etc.).
+
+    Usage:
+        async def test_my_integration(configure_astrolabe_for_mcp_server):
+            await configure_astrolabe_for_mcp_server(
+                mcp_server_internal_url="http://mcp-oauth:8001",
+                mcp_server_public_url="http://localhost:8001"
+            )
+            # ... test Astrolabe integration ...
+
+    Args:
+        nc_client: NextcloudClient fixture for occ command execution
+
+    Returns:
+        Async function that accepts:
+            - mcp_server_internal_url: Internal Docker URL for PHP app to call MCP APIs
+            - mcp_server_public_url: Public URL for OAuth token audience validation
+            - client_id: Optional OAuth client ID (default: "nextcloudMcpServerUIPublicClient")
+    """
+
+    async def _configure(
+        mcp_server_internal_url: str,
+        mcp_server_public_url: str,
+        client_id: str = "nextcloudMcpServerUIPublicClient",
+    ) -> dict[str, str]:
+        """Configure Astrolabe for the specified MCP server.
+
+        Returns:
+            Dict with client_id and client_secret
+        """
+        logger.info(
+            f"Configuring Astrolabe for MCP server: {mcp_server_internal_url} (public: {mcp_server_public_url})"
+        )
+
+        # Configure MCP server URLs in Nextcloud system config
+        result = subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "app",
+                "php",
+                "/var/www/html/occ",
+                "config:system:set",
+                "mcp_server_url",
+                "--value",
+                mcp_server_internal_url,
+            ],
+            capture_output=True,
+            text=True,
+        )
+
+        if result.returncode != 0:
+            raise RuntimeError(
+                f"Failed to configure MCP server URL. "
+                f"Command failed with code {result.returncode}. "
+                f"stderr: {result.stderr}, stdout: {result.stdout}"
+            )
+
+        # Verify mcp_server_url was actually set
+        verify_result = subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "app",
+                "php",
+                "/var/www/html/occ",
+                "config:system:get",
+                "mcp_server_url",
+            ],
+            capture_output=True,
+            text=True,
+        )
+
+        actual_url = verify_result.stdout.strip()
+        if actual_url != mcp_server_internal_url:
+            raise RuntimeError(
+                f"MCP server URL verification failed. "
+                f"Expected: {mcp_server_internal_url}, Got: {actual_url}"
+            )
+
+        logger.info(f"✓ MCP server URL configured and verified: {actual_url}")
+
+        # Configure public URL
+        result = subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "app",
+                "php",
+                "/var/www/html/occ",
+                "config:system:set",
+                "mcp_server_public_url",
+                "--value",
+                mcp_server_public_url,
+            ],
+            capture_output=True,
+            text=True,
+        )
+
+        if result.returncode != 0:
+            raise RuntimeError(
+                f"Failed to configure MCP server public URL. "
+                f"Command failed with code {result.returncode}. "
+                f"stderr: {result.stderr}, stdout: {result.stdout}"
+            )
+
+        logger.info(f"✓ MCP server public URL configured: {mcp_server_public_url}")
+
+        # Remove existing OAuth client if it exists
+        try:
+            subprocess.run(
+                [
+                    "docker",
+                    "compose",
+                    "exec",
+                    "-T",
+                    "app",
+                    "php",
+                    "/var/www/html/occ",
+                    "oidc:remove",
+                    client_id,
+                ],
+                check=False,  # Don't fail if client doesn't exist
+                capture_output=True,
+            )
+            logger.info(f"Removed existing OAuth client: {client_id}")
+        except Exception:
+            pass
+
+        # Create OAuth client for Astrolabe
+        redirect_uri = "http://localhost:8080/apps/astrolabe/oauth/callback"
+
+        result = subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "app",
+                "php",
+                "/var/www/html/occ",
+                "oidc:create",
+                "Astrolabe",
+                redirect_uri,
+                "--client_id",
+                client_id,
+                "--type",
+                "confidential",
+                "--flow",
+                "code",
+                "--token_type",
+                "jwt",
+                "--resource_url",
+                mcp_server_public_url,
+                "--allowed_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",
+            ],
+            check=True,
+            capture_output=True,
+            text=True,
+        )
+
+        # Parse client_secret from JSON output
+        client_output = json.loads(result.stdout.strip())
+        client_secret = client_output.get("client_secret")
+
+        if not client_secret:
+            raise ValueError(
+                "Failed to extract client_secret from OAuth client creation"
+            )
+
+        logger.info(f"✓ OAuth client created: {client_id}")
+
+        # Store client credentials in Nextcloud system config
+        subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "app",
+                "php",
+                "/var/www/html/occ",
+                "config:system:set",
+                "astrolabe_client_id",
+                "--value",
+                client_id,
+            ],
+            check=True,
+            capture_output=True,
+        )
+
+        subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "app",
+                "php",
+                "/var/www/html/occ",
+                "config:system:set",
+                "astrolabe_client_secret",
+                "--value",
+                client_secret,
+            ],
+            check=True,
+            capture_output=True,
+        )
+
+        logger.info("✓ Client credentials stored in system config")
+        logger.info(f"Astrolabe configured for MCP server: {mcp_server_public_url}")
+
+        return {"client_id": client_id, "client_secret": client_secret}
+
+    return _configure

tests/integration/client/test_document_processing_progress.py

@@ -1,6 +1,7 @@
 """Integration tests for document processing with progress notifications."""
 
 import io
+import os
 
 import pytest
 from PIL import Image
@@ -13,7 +14,6 @@ class TestDocumentProcessingProgress:
 
     async def test_unstructured_processor_with_progress_callback(self, nc_client):
         """Test that UnstructuredProcessor calls progress callback during processing."""
-        import os
 
         # Skip if unstructured is not enabled
         if os.getenv("ENABLE_UNSTRUCTURED", "false").lower() != "true":
@@ -71,7 +71,6 @@ class TestDocumentProcessingProgress:
         self, nc_mcp_client, nc_client
     ):
         """Test that reading a document via WebDAV MCP tool sends progress notifications."""
-        import os
 
         # Skip if document processing is not enabled
         if os.getenv("ENABLE_DOCUMENT_PROCESSING", "false").lower() != "true":
@@ -110,7 +109,6 @@ class TestDocumentProcessingProgress:
 
     async def test_progress_callback_not_required(self, nc_client):
         """Test that processing works without progress callback (backward compatibility)."""
-        import os
 
         if os.getenv("ENABLE_UNSTRUCTURED", "false").lower() != "true":
             pytest.skip("Unstructured processor not enabled")

tests/integration/conftest.py

@@ -4,6 +4,12 @@ This conftest.py provides hooks and fixtures specific to integration tests,
 including the --provider flag for RAG tests.
 """
 
+import logging
+
+import pytest
+
+logger = logging.getLogger(__name__)
+
 # Valid provider names
 VALID_PROVIDERS = ["openai", "ollama", "anthropic", "bedrock"]
 
@@ -24,3 +30,89 @@ def pytest_configure(config):
     config.addinivalue_line(
         "markers", "rag: mark test as RAG integration test (requires --provider flag)"
     )
+
+
+@pytest.fixture(autouse=True, scope="module")
+async def reset_all_singletons():
+    """Reset ALL global singletons between test modules.
+
+    Prevents anyio.WouldBlock errors caused by stale singleton state
+    from previous test modules holding references to dead event loops
+    or closed memory streams.
+    """
+    # Import all modules with singletons
+    import nextcloud_mcp_server.app as app_module
+    import nextcloud_mcp_server.auth.client_registry as client_registry_module
+    import nextcloud_mcp_server.auth.token_exchange as token_exchange_module
+    import nextcloud_mcp_server.embedding.service as embedding_module
+    import nextcloud_mcp_server.observability.tracing as tracing_module
+    import nextcloud_mcp_server.providers.registry as registry_module
+    import nextcloud_mcp_server.vector.qdrant_client as qdrant_module
+
+    # Store originals for restoration after test
+    originals = {
+        "qdrant_client": qdrant_module._qdrant_client,
+        "embedding_service": embedding_module._embedding_service,
+        "bm25_service": embedding_module._bm25_service,
+        "provider": registry_module._provider,
+        "vector_sync_state": (
+            app_module._vector_sync_state.document_send_stream,
+            app_module._vector_sync_state.document_receive_stream,
+            app_module._vector_sync_state.shutdown_event,
+            app_module._vector_sync_state.scanner_wake_event,
+        ),
+        "tracer": tracing_module._tracer,
+        "registry": client_registry_module._registry,
+        "token_exchange_service": token_exchange_module._token_exchange_service,
+    }
+
+    # Close any open memory streams before reset
+    if app_module._vector_sync_state.document_send_stream is not None:
+        try:
+            await app_module._vector_sync_state.document_send_stream.aclose()
+        except Exception:
+            pass
+    if app_module._vector_sync_state.document_receive_stream is not None:
+        try:
+            await app_module._vector_sync_state.document_receive_stream.aclose()
+        except Exception:
+            pass
+
+    # Reset all singletons to None/fresh state
+    qdrant_module._qdrant_client = None
+    embedding_module._embedding_service = None
+    embedding_module._bm25_service = None
+    registry_module._provider = None
+    app_module._vector_sync_state.document_send_stream = None
+    app_module._vector_sync_state.document_receive_stream = None
+    app_module._vector_sync_state.shutdown_event = None
+    app_module._vector_sync_state.scanner_wake_event = None
+    tracing_module._tracer = None
+    client_registry_module._registry = None
+    token_exchange_module._token_exchange_service = None
+
+    logger.debug("All singletons reset for test module")
+
+    yield
+
+    # Cleanup: Close async resources created during test
+    if qdrant_module._qdrant_client is not None:
+        try:
+            await qdrant_module._qdrant_client.close()
+        except Exception:
+            pass
+
+    # Restore originals
+    qdrant_module._qdrant_client = originals["qdrant_client"]
+    embedding_module._embedding_service = originals["embedding_service"]
+    embedding_module._bm25_service = originals["bm25_service"]
+    registry_module._provider = originals["provider"]
+    (
+        app_module._vector_sync_state.document_send_stream,
+        app_module._vector_sync_state.document_receive_stream,
+        app_module._vector_sync_state.shutdown_event,
+        app_module._vector_sync_state.scanner_wake_event,
+    ) = originals["vector_sync_state"]
+    tracing_module._tracer = originals["tracer"]
+    client_registry_module._registry = originals["registry"]
+    token_exchange_module._token_exchange_service = originals["token_exchange_service"]

tests/integration/test_app_password_provisioning.py

@@ -0,0 +1,262 @@
+"""Integration tests for app password provisioning via management API.
+
+Tests the complete flow for multi-user BasicAuth mode:
+1. User stores app password via management API endpoint
+2. MCP server stores it locally (encrypted)
+3. Background sync uses locally stored password to access Nextcloud
+
+These tests verify that BasicAuth and OAuth are completely separate concerns
+with no fallback between them.
+"""
+
+import tempfile
+from pathlib import Path
+
+import pytest
+from cryptography.fernet import Fernet
+
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+from nextcloud_mcp_server.vector.oauth_sync import (
+    NotProvisionedError,
+    get_user_client,
+    get_user_client_basic_auth,
+    get_user_client_oauth,
+)
+
+
+@pytest.fixture
+def encryption_key():
+    """Generate a test encryption key."""
+    return Fernet.generate_key().decode()
+
+
+@pytest.fixture
+async def temp_storage(encryption_key):
+    """Create temporary storage instance with encryption for testing."""
+    with tempfile.TemporaryDirectory() as tmpdir:
+        db_path = Path(tmpdir) / "test_provisioning.db"
+        storage = RefreshTokenStorage(
+            db_path=str(db_path), encryption_key=encryption_key
+        )
+        await storage.initialize()
+        yield storage
+
+
+@pytest.mark.integration
+async def test_basic_auth_mode_uses_local_storage(temp_storage, mocker):
+    """Test that BasicAuth mode uses locally stored app passwords.
+
+    In multi-user BasicAuth mode, app passwords are stored locally
+    in the MCP server's database after being provisioned via the API.
+    """
+    # Store an app password in local storage
+    await temp_storage.store_app_password("test_user", "JHWzB-ZYgLZ-3qBDj-ZQe5o-LdKpB")
+
+    # Call get_user_client_basic_auth with local storage
+    client = await get_user_client_basic_auth(
+        user_id="test_user",
+        nextcloud_host="http://localhost:8080",
+        storage=temp_storage,
+    )
+
+    # Verify client was created with correct credentials
+    assert client is not None
+    assert client.username == "test_user"
+
+
+@pytest.mark.integration
+async def test_basic_auth_mode_raises_error_without_app_password(temp_storage):
+    """Test that BasicAuth mode raises NotProvisionedError if no app password.
+
+    There is NO fallback to OAuth - if no app password, user must provision one.
+    """
+    # Don't store any app password
+
+    # Call get_user_client_basic_auth - should raise NotProvisionedError
+    with pytest.raises(NotProvisionedError) as exc_info:
+        await get_user_client_basic_auth(
+            user_id="test_user",
+            nextcloud_host="http://localhost:8080",
+            storage=temp_storage,
+        )
+
+    # Verify error message mentions app password provisioning
+    assert "app password" in str(exc_info.value).lower()
+    assert "test_user" in str(exc_info.value)
+
+
+@pytest.mark.integration
+async def test_get_user_client_dispatches_to_basic_auth(temp_storage, mocker):
+    """Test that get_user_client dispatches to BasicAuth mode correctly."""
+    # Store an app password
+    await temp_storage.store_app_password("alice", "aaaaa-bbbbb-ccccc-ddddd-eeeee")
+
+    # Mock RefreshTokenStorage.from_env at the source module
+    mocker.patch(
+        "nextcloud_mcp_server.auth.storage.RefreshTokenStorage.from_env",
+        return_value=temp_storage,
+    )
+    # Also mock initialize since from_env returns an uninitialized instance
+    mocker.patch.object(temp_storage, "initialize", return_value=None)
+
+    # Call get_user_client in BasicAuth mode
+    client = await get_user_client(
+        user_id="alice",
+        token_broker=None,  # No token broker needed for BasicAuth mode
+        nextcloud_host="http://localhost:8080",
+        use_basic_auth=True,
+    )
+
+    # Verify client was created successfully
+    assert client is not None
+    assert client.username == "alice"
+
+
+@pytest.mark.integration
+async def test_oauth_mode_uses_refresh_token_only(mocker):
+    """Test that OAuth mode uses ONLY refresh tokens, NOT app passwords.
+
+    In OAuth mode, app passwords are NOT used.
+    This is a complete separation of concerns.
+    """
+    from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
+
+    # Mock TokenBrokerService to return an access token
+    mock_token_broker = mocker.AsyncMock(spec=TokenBrokerService)
+    mock_token_broker.get_background_token.return_value = "test-access-token"
+
+    # Call get_user_client in OAuth mode
+    _client = await get_user_client(
+        user_id="test_user",
+        token_broker=mock_token_broker,
+        nextcloud_host="http://localhost:8080",
+        use_basic_auth=False,  # OAuth mode
+    )
+
+    # Verify token broker was called
+    mock_token_broker.get_background_token.assert_called_once()
+
+
+@pytest.mark.integration
+async def test_oauth_mode_raises_error_without_token(mocker):
+    """Test that OAuth mode raises NotProvisionedError if no refresh token.
+
+    There is NO fallback to app passwords - if no token, user must provision.
+    """
+    from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
+
+    # Mock TokenBrokerService to return None (no token)
+    mock_token_broker = mocker.AsyncMock(spec=TokenBrokerService)
+    mock_token_broker.get_background_token.return_value = None
+
+    # Call get_user_client in OAuth mode - should raise NotProvisionedError
+    with pytest.raises(NotProvisionedError) as exc_info:
+        await get_user_client(
+            user_id="test_user",
+            token_broker=mock_token_broker,
+            nextcloud_host="http://localhost:8080",
+            use_basic_auth=False,
+        )
+
+    # Verify error message mentions OAuth provisioning
+    assert "oauth" in str(exc_info.value).lower()
+    assert "test_user" in str(exc_info.value)
+
+
+@pytest.mark.integration
+async def test_get_user_client_oauth_function(mocker):
+    """Test the dedicated get_user_client_oauth function."""
+    from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
+
+    # Mock TokenBrokerService
+    mock_token_broker = mocker.AsyncMock(spec=TokenBrokerService)
+    mock_token_broker.get_background_token.return_value = "test-bearer-token"
+
+    # Call dedicated function
+    client = await get_user_client_oauth(
+        user_id="alice",
+        token_broker=mock_token_broker,
+        nextcloud_host="http://localhost:8080",
+    )
+
+    assert client is not None
+    assert client.username == "alice"
+    mock_token_broker.get_background_token.assert_called_once()
+
+
+@pytest.mark.integration
+async def test_oauth_mode_requires_token_broker():
+    """Test that OAuth mode requires a token broker."""
+    with pytest.raises(ValueError, match="token_broker required"):
+        await get_user_client(
+            user_id="test_user",
+            token_broker=None,  # Missing token broker
+            nextcloud_host="http://localhost:8080",
+            use_basic_auth=False,  # OAuth mode
+        )
+
+
+@pytest.mark.integration
+async def test_multiple_users_basic_auth_mode(temp_storage, mocker):
+    """Test that multiple users can be provisioned independently."""
+    # Store app passwords for multiple users
+    users = {
+        "alice": "aaaaa-aaaaa-aaaaa-aaaaa-aaaaa",
+        "bob": "bbbbb-bbbbb-bbbbb-bbbbb-bbbbb",
+        "charlie": "ccccc-ccccc-ccccc-ccccc-ccccc",
+    }
+
+    for user_id, password in users.items():
+        await temp_storage.store_app_password(user_id, password)
+
+    # Verify each user can get a client
+    for user_id in users.keys():
+        client = await get_user_client_basic_auth(
+            user_id=user_id,
+            nextcloud_host="http://localhost:8080",
+            storage=temp_storage,
+        )
+        assert client is not None
+        assert client.username == user_id
+
+
+@pytest.mark.integration
+async def test_get_all_provisioned_users(temp_storage):
+    """Test that we can list all provisioned users for BasicAuth mode."""
+    # Store app passwords for multiple users
+    await temp_storage.store_app_password("alice", "aaaaa-aaaaa-aaaaa-aaaaa-aaaaa")
+    await temp_storage.store_app_password("bob", "bbbbb-bbbbb-bbbbb-bbbbb-bbbbb")
+
+    # Get all provisioned users
+    user_ids = await temp_storage.get_all_app_password_user_ids()
+
+    assert len(user_ids) == 2
+    assert "alice" in user_ids
+    assert "bob" in user_ids
+
+
+@pytest.mark.integration
+async def test_revoke_app_password(temp_storage):
+    """Test that deleting app password revokes background access."""
+    # Provision user
+    await temp_storage.store_app_password("alice", "aaaaa-aaaaa-aaaaa-aaaaa-aaaaa")
+
+    # Verify user is provisioned
+    user_ids = await temp_storage.get_all_app_password_user_ids()
+    assert "alice" in user_ids
+
+    # Revoke access
+    deleted = await temp_storage.delete_app_password("alice")
+    assert deleted is True
+
+    # Verify user is no longer provisioned
+    user_ids = await temp_storage.get_all_app_password_user_ids()
+    assert "alice" not in user_ids
+
+    # Verify get_user_client now raises NotProvisionedError
+    with pytest.raises(NotProvisionedError):
+        await get_user_client_basic_auth(
+            user_id="alice",
+            nextcloud_host="http://localhost:8080",
+            storage=temp_storage,
+        )

tests/integration/test_astrolabe_multi_user_background_sync.py

@@ -0,0 +1,817 @@
+"""Integration test for multi-user Astrolabe background sync enablement.
+
+This test verifies that multiple users can independently:
+1. Log in to Nextcloud
+2. Generate an app password in Security settings
+3. Enter the app password in Astrolabe personal settings
+4. Enable background sync for the mcp-multi-user-basic service
+5. Verify app password is stored in the database
+
+Tests the complete app password provisioning flow:
+user login → Security settings → app password generation → Astrolabe settings →
+app password entry → background sync activation → database verification.
+"""
+
+import logging
+import re
+import subprocess
+
+import anyio
+import pytest
+from playwright.async_api import Page
+
+logger = logging.getLogger(__name__)
+
+pytestmark = [pytest.mark.integration, pytest.mark.oauth]
+
+
+async def login_to_nextcloud(page: Page, username: str, password: str):
+    """Helper function to login to Nextcloud via Playwright.
+
+    Args:
+        page: Playwright page instance
+        username: Nextcloud username
+        password: Nextcloud password
+    """
+    nextcloud_url = "http://localhost:8080"
+
+    logger.info(f"Logging in to Nextcloud as {username}...")
+    await page.goto(f"{nextcloud_url}/login", wait_until="networkidle")
+
+    # Fill in login form
+    await page.wait_for_selector('input[name="user"]', timeout=10000)
+    await page.fill('input[name="user"]', username)
+    await page.fill('input[name="password"]', password)
+
+    # Submit form
+    await page.click('button[type="submit"]')
+    await page.wait_for_load_state("networkidle", timeout=30000)
+
+    # Verify logged in (should redirect away from login page)
+    current_url = page.url
+    assert "/login" not in current_url, (
+        f"Login failed for {username}, still on login page"
+    )
+    logger.info(f"✓ Successfully logged in as {username}")
+
+
+async def navigate_to_astrolabe_settings(page: Page):
+    """Navigate to Astrolabe personal settings page.
+
+    Args:
+        page: Playwright page instance (must be authenticated)
+    """
+    nextcloud_url = "http://localhost:8080"
+    settings_url = f"{nextcloud_url}/settings/user/astrolabe"
+
+    logger.info(f"Navigating to Astrolabe settings: {settings_url}")
+    await page.goto(settings_url, wait_until="networkidle", timeout=30000)
+
+    # Verify we're on the settings page
+    current_url = page.url
+    assert "/settings/user/astrolabe" in current_url, (
+        f"Failed to navigate to Astrolabe settings, current URL: {current_url}"
+    )
+    logger.info("✓ Successfully loaded Astrolabe settings page")
+
+
+async def generate_app_password(
+    page: Page, username: str, app_name: str = "Astrolabe Background Sync"
+) -> str:
+    """Generate an app password in Nextcloud Security settings.
+
+    Args:
+        page: Playwright page instance (must be authenticated)
+        username: Username (for logging)
+        app_name: Name for the app password
+
+    Returns:
+        The generated app password string
+    """
+    logger.info(f"Generating app password for {username}...")
+
+    nextcloud_url = "http://localhost:8080"
+
+    # Navigate to Security settings
+    await page.goto(f"{nextcloud_url}/settings/user/security", wait_until="networkidle")
+    logger.info("Navigated to Security settings")
+
+    # Fill the app password input field (selector confirmed via Playwright MCP)
+    app_password_input = page.locator('input[placeholder="App name"]')
+    await app_password_input.fill(app_name)
+    logger.info(f"Entered app name: {app_name}")
+
+    # Wait for Vue.js to react and enable the button (needs 1 second, not 0.5)
+    await anyio.sleep(1.0)
+    logger.info("Waited for Vue.js to process input and enable button")
+
+    # Click the create button
+    create_button = page.locator(
+        'button[type="submit"]:has-text("Create new app password")'
+    )
+    await create_button.click()
+    logger.info("Clicked create app password button")
+
+    # Wait for app password to be generated and displayed in the dialog
+    await anyio.sleep(3)  # Give it more time to generate and display
+
+    # Find the Login input field which should have the username value
+    # Then find the Password input field which is in the same form
+    app_password = None
+    try:
+        # Wait for heading "New app password" to appear
+        await page.wait_for_selector('text="New app password"', timeout=10000)
+        logger.info("App password dialog appeared with heading")
+
+        # Get all visible input elements
+        all_inputs = await page.locator('input[type="text"]').all()
+        logger.info(f"Found {len(all_inputs)} text input elements")
+
+        # Check each input to find the one with the app password
+        for idx, input_elem in enumerate(all_inputs):
+            try:
+                value = await input_elem.input_value()
+                if value and "-" in value and len(value) > 20:
+                    app_password = value.strip()
+                    logger.info(
+                        f"Found app password in input {idx}: '{app_password}' (length: {len(app_password)})"
+                    )
+                    break
+            except Exception as e:
+                logger.debug(f"Could not get value from input {idx}: {e}")
+                continue
+
+    except Exception as e:
+        logger.error(f"Failed to find app password dialog or extract password: {e}")
+
+    if not app_password:
+        # Take screenshot for debugging
+        screenshot_path = f"/tmp/app_password_generation_{username}.png"
+        await page.screenshot(path=screenshot_path)
+        raise ValueError(
+            f"Could not find generated app password. Screenshot: {screenshot_path}"
+        )
+
+    # Validate password format before returning
+
+    if not re.match(
+        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}$",
+        app_password,
+    ):
+        logger.error(
+            f"Extracted password does not match expected format: '{app_password}'"
+        )
+        logger.error(f"Password repr: {repr(app_password)}")
+        screenshot_path = f"/tmp/app_password_invalid_format_{username}.png"
+        await page.screenshot(path=screenshot_path)
+        raise ValueError(
+            f"App password format validation failed. Screenshot: {screenshot_path}"
+        )
+
+    logger.info(
+        f"✓ Generated app password for {username}: {app_password[:10]}... (validated)"
+    )
+
+    # Close the dialog by clicking the Close button
+    close_button = page.get_by_role("button", name="Close")
+    await close_button.click()
+    logger.info("Closed app password dialog")
+    await anyio.sleep(0.5)
+
+    return app_password
+
+
+async def enable_background_sync_via_app_password(
+    page: Page, username: str, app_password: str
+):
+    """Enable background sync by entering app password in Astrolabe settings.
+
+    Args:
+        page: Playwright page instance
+        username: Username (for logging)
+        app_password: App password to enter
+
+    Returns:
+        True if background sync was enabled successfully
+    """
+    logger.info(f"Enabling background sync via app password for {username}...")
+
+    nextcloud_url = "http://localhost:8080"
+
+    # Set up network request and console listeners BEFORE navigation
+    network_requests = []
+    network_responses = []
+    console_messages = []
+
+    def log_request(req):
+        network_requests.append(f"{req.method} {req.url}")
+
+    def log_response(resp):
+        response_info = f"{resp.status} {resp.url}"
+        network_responses.append(response_info)
+        logger.info(f"Response: {response_info}")
+
+    def log_console(msg):
+        console_messages.append(f"[{msg.type}] {msg.text}")
+
+    page.on("request", log_request)
+    page.on("response", log_response)
+    page.on("console", log_console)
+
+    # Navigate to Astrolabe settings
+    await page.goto(
+        f"{nextcloud_url}/settings/user/astrolabe", wait_until="networkidle"
+    )
+
+    # Wait for page to load
+    await anyio.sleep(1)
+
+    # Check if already active (look for "Active" text in the Background Sync Access section)
+    try:
+        # The "Active" badge appears as a <span> with text "Active"
+        active_text = page.get_by_text("Active", exact=True)
+        if await active_text.is_visible(timeout=2000):
+            logger.info(f"✓ Background sync already active for {username}")
+            return True
+    except Exception:
+        pass
+
+    # Find the app password input field using the placeholder text
+    # Based on manual testing: textbox with placeholder "xxxxx-xxxxx-xxxxx-xxxxx-xxxxx"
+    app_password_input = page.get_by_placeholder("xxxxx-xxxxx-xxxxx-xxxxx-xxxxx")
+
+    try:
+        await app_password_input.wait_for(timeout=5000, state="visible")
+        logger.info("Found app password input field")
+    except Exception:
+        # Take screenshot for debugging
+        screenshot_path = f"/tmp/astrolabe_no_password_field_{username}.png"
+        await page.screenshot(path=screenshot_path)
+        raise ValueError(
+            f"Could not find app password input field for {username}. Screenshot: {screenshot_path}"
+        )
+
+    # Enter the app password
+    await app_password_input.fill(app_password)
+    logger.info(f"Entered app password for {username}")
+
+    # Wait a moment for any validation to complete
+    await anyio.sleep(0.5)
+
+    # Take screenshot before clicking Save to check for warnings
+    screenshot_path = f"/tmp/before_save_{username}.png"
+    await page.screenshot(path=screenshot_path)
+    logger.info(f"Screenshot taken before Save: {screenshot_path}")
+
+    # Find and click the Save button
+    save_button = page.get_by_role("button", name="Save")
+
+    # Check if Save button is enabled
+    is_disabled = await save_button.is_disabled()
+    logger.info(f"Save button disabled state: {is_disabled}")
+
+    await save_button.click()
+    logger.info("Clicked Save button")
+
+    # Give the request time to complete before checking logs
+    await anyio.sleep(0.5)
+
+    # Log network requests after clicking Save
+    logger.info(f"Network requests after Save for {username}:")
+    for req in network_requests[-10:]:  # Last 10 requests
+        logger.info(f"  {req}")
+
+    # Log network responses after clicking Save
+    logger.info(f"Network responses after Save for {username}:")
+    for resp in network_responses[-10:]:  # Last 10 responses
+        logger.info(f"  {resp}")
+
+    # Check specifically for the credentials POST response
+    credentials_responses = [
+        r for r in network_responses if "background-sync/credentials" in r
+    ]
+    if credentials_responses:
+        logger.info(f"Credentials endpoint response: {credentials_responses[-1]}")
+        if "200" not in credentials_responses[-1]:
+            logger.error(
+                f"Credentials POST did not return 200 OK: {credentials_responses[-1]}"
+            )
+    else:
+        logger.warning("No response found for credentials endpoint!")
+
+    # Wait for the page to reload after successful save
+    # The JavaScript in personalSettings.js does: setTimeout(() => window.location.reload(), 1000)
+    await page.wait_for_load_state("networkidle", timeout=15000)
+    await anyio.sleep(2)
+
+    # Log any console messages
+    if console_messages:
+        logger.info(f"Console messages for {username}:")
+        for msg in console_messages:
+            logger.info(f"  {msg}")
+
+    # Check for error notifications (toast messages)
+    try:
+        error_toast = page.locator(".toastify.toast-error, .toast-error")
+        if await error_toast.count() > 0:
+            error_text = await error_toast.first.text_content()
+            logger.error(f"Error notification for {username}: {error_text}")
+    except Exception:
+        pass
+
+    # Verify "Active" text appears after reload
+    try:
+        active_text = page.get_by_text("Active", exact=True)
+        await active_text.wait_for(timeout=5000, state="visible")
+        logger.info(f"✓ Background sync enabled for {username} - Active badge visible")
+        return True
+    except Exception:
+        # Take screenshot for debugging
+        screenshot_path = f"/tmp/astrolabe_after_password_{username}.png"
+        await page.screenshot(path=screenshot_path)
+        logger.error(
+            f"Active badge did not appear for {username}. Screenshot: {screenshot_path}"
+        )
+        raise
+
+
+async def verify_app_password_created(username: str) -> bool:
+    """Verify that background sync app password was stored for the user.
+
+    This checks the Nextcloud database for background sync credentials stored
+    by Astrolabe in the oc_preferences table.
+
+    Args:
+        username: Nextcloud username
+
+    Returns:
+        True if background sync app password exists
+    """
+    logger.info(f"Verifying background sync app password for {username}...")
+
+    # Query the database to check for background sync credentials
+    # Astrolabe stores app passwords in oc_preferences, not oc_authtoken
+
+    query = f"""
+    SELECT userid, configkey, configvalue
+    FROM oc_preferences
+    WHERE userid = '{username}'
+    AND appid = 'astrolabe'
+    AND configkey IN ('background_sync_password', 'background_sync_type', 'background_sync_provisioned_at')
+    ORDER BY configkey;
+    """
+
+    try:
+        result = subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "db",
+                "mariadb",
+                "-u",
+                "root",
+                "-ppassword",
+                "nextcloud",
+                "-e",
+                query,
+            ],
+            capture_output=True,
+            text=True,
+            timeout=10,
+        )
+
+        output = result.stdout
+        logger.debug(f"Background sync credentials query result:\n{output}")
+
+        # Check if background sync credentials exist
+        # We should see 3 rows: background_sync_password, background_sync_type, background_sync_provisioned_at
+        lines = output.strip().split("\n")
+
+        if len(lines) >= 3:  # Header + at least 2 data rows (password + type)
+            # Verify background_sync_type is "app_password"
+            if "app_password" in output:
+                logger.info(f"✓ Background sync app password stored for {username}")
+                return True
+            else:
+                logger.warning(
+                    f"Background sync credentials found but type is not app_password for {username}"
+                )
+                return False
+        else:
+            logger.warning(f"No background sync credentials found for {username}")
+            return False
+
+    except Exception as e:
+        logger.error(f"Error checking background sync credentials for {username}: {e}")
+        return False
+
+
+@pytest.mark.integration
+@pytest.mark.oauth
+async def test_multi_user_astrolabe_background_sync_enablement(
+    browser,
+    nc_client,
+    test_users_setup,
+    configure_astrolabe_for_mcp_server,
+):
+    """Test that multiple users can independently enable background sync via app passwords.
+
+    This test verifies the complete app password provisioning flow:
+    1. Users log in to Nextcloud
+    2. Users generate app passwords in Security settings
+    3. Users navigate to Astrolabe personal settings
+    4. Users enter their app passwords in the Astrolabe form
+    5. Background sync becomes active with "Active" badge
+    6. App passwords are stored in the database (oc_authtoken table)
+    7. The process works correctly for multiple users
+
+    Requirements:
+    - Astrolabe app installed in Nextcloud and configured for mcp-multi-user-basic
+    - MCP server running in multi-user BasicAuth mode (mcp-multi-user-basic service)
+    - Test users (alice, bob) created with valid credentials
+
+    This tests ADR-002 Tier 2 authentication: User-specific app passwords for background operations
+    in multi-user BasicAuth deployments.
+    """
+    # Configure Astrolabe to point to the mcp-multi-user-basic server
+    logger.info("Configuring Astrolabe for mcp-multi-user-basic server...")
+    await configure_astrolabe_for_mcp_server(
+        mcp_server_internal_url="http://mcp-multi-user-basic:8000",
+        mcp_server_public_url="http://localhost:8003",
+    )
+
+    # Test users to check
+    test_users = ["alice", "bob"]
+
+    # Verify test users were created by the fixture
+    logger.info("Verifying test users exist in Nextcloud...")
+    for username in test_users:
+        try:
+            # Use nc_client to check if user exists
+            user_details = await nc_client.users.get_user_details(username)
+            logger.info(
+                f"✓ Confirmed {username} exists (display name: {user_details.displayname})"
+            )
+        except Exception as e:
+            raise AssertionError(
+                f"Test user {username} does not exist! "
+                f"test_users_setup fixture may have failed. Error: {e}"
+            )
+
+    results = {}
+
+    for username in test_users:
+        logger.info(f"\n{'=' * 60}")
+        logger.info(f"Testing background sync enablement for: {username}")
+        logger.info(f"{'=' * 60}")
+
+        user_config = test_users_setup[username]
+        password = user_config["password"]
+
+        # Create new browser context for this user
+        context = await browser.new_context(ignore_https_errors=True)
+        page = await context.new_page()
+
+        try:
+            # Step 1: Login to Nextcloud
+            await login_to_nextcloud(page, username, password)
+
+            # Step 2: Generate app password in Security settings
+            app_password = await generate_app_password(page, username)
+
+            # Step 3: Enable background sync by entering app password in Astrolabe
+            sync_enabled = await enable_background_sync_via_app_password(
+                page, username, app_password
+            )
+
+            # Step 4: Verify app password was stored in database
+            app_password_stored = await verify_app_password_created(username)
+
+            # Give it time to complete
+            await anyio.sleep(1)
+
+            results[username] = {
+                "settings_accessed": True,
+                "app_password_generated": bool(app_password),
+                "sync_enabled": sync_enabled,
+                "app_password_stored": app_password_stored,
+                "background_sync_active": sync_enabled and app_password_stored,
+            }
+
+            logger.info(f"\n{username} results:")
+            logger.info("  Settings accessed: ✓")
+            logger.info(f"  App password generated: {'✓' if app_password else '✗'}")
+            logger.info(f"  Sync enabled: {'✓' if sync_enabled else '✗'}")
+            logger.info(f"  App password stored: {'✓' if app_password_stored else '✗'}")
+            logger.info(
+                f"  Background sync active: {'✓' if (sync_enabled and app_password_stored) else '✗'}"
+            )
+
+        except Exception as e:
+            logger.error(f"Error during {username} test: {e}")
+            results[username] = {
+                "settings_accessed": False,
+                "app_password_generated": False,
+                "sync_enabled": False,
+                "app_password_stored": False,
+                "background_sync_active": False,
+                "error": str(e),
+            }
+
+        finally:
+            await context.close()
+
+    # Verify all users succeeded
+    logger.info(f"\n{'=' * 60}")
+    logger.info("Test Summary")
+    logger.info(f"{'=' * 60}")
+
+    for username, result in results.items():
+        logger.info(f"\n{username}:")
+        for key, value in result.items():
+            if key != "error":
+                status = "✓" if value else "✗"
+                logger.info(f"  {key}: {status}")
+            elif value:
+                logger.info(f"  error: {value}")
+
+    # Assert all users successfully enabled background sync
+    for username in test_users:
+        result = results[username]
+        assert result["settings_accessed"], (
+            f"{username} could not access Astrolabe settings"
+        )
+        assert result["app_password_generated"], (
+            f"{username} app password was not generated"
+        )
+        assert result["sync_enabled"], (
+            f"{username} background sync enablement did not complete successfully"
+        )
+        assert result["app_password_stored"], (
+            f"{username} app password was not stored in database"
+        )
+        assert result["background_sync_active"], (
+            f"{username} background sync is not active"
+        )
+
+    logger.info(
+        f"\n✓ All {len(test_users)} users successfully enabled background sync via app passwords!"
+    )
+
+
+async def revoke_background_sync_access(page: Page, username: str) -> bool:
+    """Revoke background sync access by clicking the Revoke Access button.
+
+    Args:
+        page: Playwright page instance (must be authenticated)
+        username: Username (for logging)
+
+    Returns:
+        True if revocation was successful
+    """
+    logger.info(f"Revoking background sync access for {username}...")
+
+    nextcloud_url = "http://localhost:8080"
+
+    # Set up network request and console listeners
+    network_requests = []
+    network_responses = []
+    console_messages = []
+
+    def log_request(req):
+        network_requests.append(f"{req.method} {req.url}")
+
+    def log_response(resp):
+        response_info = f"{resp.status} {resp.url}"
+        network_responses.append(response_info)
+        logger.info(f"Response: {response_info}")
+
+    def log_console(msg):
+        console_messages.append(f"[{msg.type}] {msg.text}")
+
+    page.on("request", log_request)
+    page.on("response", log_response)
+    page.on("console", log_console)
+
+    # Navigate to Astrolabe settings
+    await page.goto(
+        f"{nextcloud_url}/settings/user/astrolabe", wait_until="networkidle"
+    )
+
+    # Wait for page to load
+    await anyio.sleep(1)
+
+    # Check if "Active" badge is visible (indicating background sync is enabled)
+    try:
+        active_text = page.get_by_text("Active", exact=True)
+        if not await active_text.is_visible(timeout=2000):
+            logger.warning(
+                f"Background sync not active for {username}, nothing to revoke"
+            )
+            return False
+    except Exception:
+        logger.warning(f"Could not find Active badge for {username}")
+        return False
+
+    # Find the "Revoke Access" button
+    revoke_button = page.get_by_role("button", name="Revoke Access")
+
+    try:
+        await revoke_button.wait_for(timeout=5000, state="visible")
+        logger.info("Found Revoke Access button")
+    except Exception:
+        screenshot_path = f"/tmp/astrolabe_no_revoke_button_{username}.png"
+        await page.screenshot(path=screenshot_path)
+        raise ValueError(
+            f"Could not find Revoke Access button for {username}. Screenshot: {screenshot_path}"
+        )
+
+    # Set up dialog handler for confirmation dialog
+    page.once("dialog", lambda dialog: dialog.accept())
+
+    # Click the Revoke Access button
+    await revoke_button.click()
+    logger.info("Clicked Revoke Access button")
+
+    # Wait for the request to complete and page to reload
+    await page.wait_for_load_state("networkidle", timeout=15000)
+    await anyio.sleep(2)
+
+    # Log network requests after clicking
+    logger.info(f"Network requests after Revoke for {username}:")
+    for req in network_requests[-10:]:
+        logger.info(f"  {req}")
+
+    # Log network responses
+    logger.info(f"Network responses after Revoke for {username}:")
+    for resp in network_responses[-10:]:
+        logger.info(f"  {resp}")
+
+    # Check specifically for the revoke POST response
+    revoke_responses = [r for r in network_responses if "credentials/revoke" in r]
+    if revoke_responses:
+        logger.info(f"Revoke endpoint response: {revoke_responses[-1]}")
+        if "200" not in revoke_responses[-1]:
+            logger.error(f"Revoke POST did not return 200 OK: {revoke_responses[-1]}")
+            return False
+    else:
+        logger.warning("No response found for credentials/revoke endpoint!")
+        # Take screenshot for debugging
+        screenshot_path = f"/tmp/astrolabe_revoke_no_response_{username}.png"
+        await page.screenshot(path=screenshot_path)
+        return False
+
+    # Log any console messages
+    if console_messages:
+        logger.info(f"Console messages for {username}:")
+        for msg in console_messages:
+            logger.info(f"  {msg}")
+
+    # Check for error notifications (toast messages)
+    try:
+        error_toast = page.locator(".toastify.toast-error, .toast-error")
+        if await error_toast.count() > 0:
+            error_text = await error_toast.first.text_content()
+            logger.error(f"Error notification for {username}: {error_text}")
+            return False
+    except Exception:
+        pass
+
+    # Verify "Active" badge is no longer visible
+    try:
+        active_text = page.get_by_text("Active", exact=True)
+        if await active_text.is_visible(timeout=2000):
+            logger.error(f"Active badge still visible for {username} after revoke!")
+            screenshot_path = f"/tmp/astrolabe_revoke_still_active_{username}.png"
+            await page.screenshot(path=screenshot_path)
+            return False
+    except Exception:
+        pass
+
+    logger.info(f"✓ Background sync access revoked for {username}")
+    return True
+
+
+async def verify_app_password_deleted(username: str) -> bool:
+    """Verify that background sync app password was deleted for the user.
+
+    Args:
+        username: Nextcloud username
+
+    Returns:
+        True if background sync credentials no longer exist
+    """
+    logger.info(f"Verifying background sync credentials deleted for {username}...")
+
+    query = f"""
+    SELECT userid, configkey, configvalue
+    FROM oc_preferences
+    WHERE userid = '{username}'
+    AND appid = 'astrolabe'
+    AND configkey IN ('background_sync_password', 'background_sync_type', 'background_sync_provisioned_at')
+    ORDER BY configkey;
+    """
+
+    try:
+        result = subprocess.run(
+            [
+                "docker",
+                "compose",
+                "exec",
+                "-T",
+                "db",
+                "mariadb",
+                "-u",
+                "root",
+                "-ppassword",
+                "nextcloud",
+                "-e",
+                query,
+            ],
+            capture_output=True,
+            text=True,
+            timeout=10,
+        )
+
+        output = result.stdout
+        logger.debug(f"Background sync credentials query result:\n{output}")
+
+        # After deletion, we should NOT see background_sync_password
+        if "background_sync_password" not in output:
+            logger.info(f"✓ Background sync credentials deleted for {username}")
+            return True
+        else:
+            logger.warning(f"Background sync credentials still exist for {username}")
+            return False
+
+    except Exception as e:
+        logger.error(f"Error checking background sync credentials for {username}: {e}")
+        return False
+
+
+@pytest.mark.integration
+@pytest.mark.oauth
+async def test_revoke_background_sync_access(
+    browser,
+    nc_client,
+    test_users_setup,
+    configure_astrolabe_for_mcp_server,
+):
+    """Test that users can revoke background sync access via the Revoke Access button.
+
+    This test verifies:
+    1. User enables background sync via app password
+    2. User clicks "Revoke Access" button
+    3. Confirmation dialog is handled
+    4. POST request is sent to /api/v1/background-sync/credentials/revoke
+    5. "Active" badge disappears from settings page
+    6. Background sync credentials are deleted from database
+
+    This tests the fix for the issue where POST requests to the revoke endpoint
+    were returning errors due to HTTP method mismatch (was DELETE, now POST).
+    """
+    # Configure Astrolabe to point to the mcp-multi-user-basic server
+    logger.info("Configuring Astrolabe for mcp-multi-user-basic server...")
+    await configure_astrolabe_for_mcp_server(
+        mcp_server_internal_url="http://mcp-multi-user-basic:8000",
+        mcp_server_public_url="http://localhost:8003",
+    )
+
+    # Test with a single user for this specific test
+    username = "alice"
+    user_config = test_users_setup[username]
+    password = user_config["password"]
+
+    # Create new browser context
+    context = await browser.new_context(ignore_https_errors=True)
+    page = await context.new_page()
+
+    try:
+        # Step 1: Login to Nextcloud
+        await login_to_nextcloud(page, username, password)
+
+        # Step 2: Generate app password and enable background sync
+        app_password = await generate_app_password(page, username)
+        await enable_background_sync_via_app_password(page, username, app_password)
+
+        # Step 3: Verify background sync is enabled
+        assert await verify_app_password_created(username), (
+            f"Background sync not enabled for {username}"
+        )
+
+        # Step 4: Revoke background sync access
+        revoke_success = await revoke_background_sync_access(page, username)
+        assert revoke_success, f"Failed to revoke background sync access for {username}"
+
+        # Step 5: Verify credentials are deleted from database
+        credentials_deleted = await verify_app_password_deleted(username)
+        assert credentials_deleted, (
+            f"Background sync credentials not deleted for {username}"
+        )
+
+        logger.info(f"\n✓ Successfully revoked background sync access for {username}!")
+
+    finally:
+        await context.close()

tests/integration/test_astrolabe_settings_buttons.py

@@ -0,0 +1,91 @@
+"""Integration tests for Astrolabe personal settings page buttons.
+
+Tests the button functionality on /settings/user/astrolabe:
+1. Disable Indexing button (POST to /apps/astrolabe/api/revoke)
+2. Disconnect button (POST to /apps/astrolabe/oauth/disconnect)
+
+These tests verify that:
+- The endpoints respond correctly to POST requests
+- CSRF token validation works
+- User actions are properly handled
+- Appropriate redirects occur
+"""
+
+import httpx
+import pytest
+
+
+@pytest.mark.integration
+async def test_disable_indexing_button_endpoint_exists():
+    """Test that the Disable Indexing endpoint is accessible."""
+    async with httpx.AsyncClient() as client:
+        # Try without authentication - should return 401 or redirect
+        response = await client.post(
+            "http://localhost:8080/apps/astrolabe/api/revoke",
+            follow_redirects=False,
+        )
+
+        # Should get 401 Unauthorized or 30x redirect
+        assert response.status_code in [401, 301, 302, 303, 307, 308], (
+            f"Expected 401 or redirect without auth, got {response.status_code}"
+        )
+
+
+@pytest.mark.integration
+async def test_disconnect_button_endpoint_exists():
+    """Test that the Disconnect endpoint is accessible."""
+    async with httpx.AsyncClient() as client:
+        # Try without authentication - should return 401 or redirect
+        response = await client.post(
+            "http://localhost:8080/apps/astrolabe/oauth/disconnect",
+            follow_redirects=False,
+        )
+
+        # Should get 401 Unauthorized or 30x redirect
+        assert response.status_code in [401, 301, 302, 303, 307, 308], (
+            f"Expected 401 or redirect without auth, got {response.status_code}"
+        )
+
+
+@pytest.mark.integration
+async def test_settings_page_renders_buttons():
+    """Test that the settings page template includes button forms.
+
+    This test verifies that the PHP template renders the form elements.
+    It doesn't require authentication since we're just checking the route exists.
+    """
+    async with httpx.AsyncClient(follow_redirects=False) as client:
+        # Try to access settings page
+        response = await client.get("http://localhost:8080/settings/user/astrolabe")
+
+        # Should get 401/redirect if not authenticated (expected)
+        # or 200 if user session exists from browser testing
+        assert response.status_code in [200, 401, 302, 303, 307, 308], (
+            f"Unexpected status code: {response.status_code}"
+        )
+
+
+@pytest.mark.integration
+@pytest.mark.skip(
+    reason="Requires manual authentication - test with Playwright instead"
+)
+async def test_disconnect_button_functionality():
+    """Test that clicking Disconnect button clears user OAuth tokens.
+
+    NOTE: This test is skipped because programmatic login to Nextcloud is complex.
+    Use Playwright-based tests or manual testing instead.
+    """
+    pass
+
+
+@pytest.mark.integration
+@pytest.mark.skip(
+    reason="Requires manual authentication - test with Playwright instead"
+)
+async def test_disable_indexing_button_functionality():
+    """Test that clicking Disable Indexing button revokes background access.
+
+    NOTE: This test is skipped because programmatic login to Nextcloud is complex.
+    Use Playwright-based tests or manual testing instead.
+    """
+    pass

tests/integration/test_deck_reorder_card.py

@@ -0,0 +1,177 @@
+"""Integration tests for Deck card reorder functionality.
+
+Tests issue #469: Moving Deck card from one column (stack) to another not working.
+https://github.com/cbcoutinho/nextcloud-mcp-server/issues/469
+"""
+
+import logging
+import uuid
+
+import pytest
+
+from nextcloud_mcp_server.client import NextcloudClient
+
+logger = logging.getLogger(__name__)
+pytestmark = pytest.mark.integration
+
+
+@pytest.fixture
+async def board_with_two_stacks(nc_client: NextcloudClient):
+    """Create a temporary board with two stacks for testing card movement.
+
+    Yields:
+        tuple: (board_data, source_stack_data, target_stack_data)
+    """
+    unique_suffix = uuid.uuid4().hex[:8]
+    board_title = f"Reorder Test Board {unique_suffix}"
+    board = None
+
+    logger.info(f"Creating board with two stacks: {board_title}")
+    try:
+        board = await nc_client.deck.create_board(board_title, "0000FF")
+        board_id = board.id
+
+        # Create source stack (stack 1)
+        source_stack = await nc_client.deck.create_stack(
+            board_id, f"Source Stack {unique_suffix}", order=1
+        )
+        source_stack_data = {
+            "id": source_stack.id,
+            "title": source_stack.title,
+            "order": source_stack.order,
+        }
+        logger.info(f"Created source stack with ID: {source_stack.id}")
+
+        # Create target stack (stack 2)
+        target_stack = await nc_client.deck.create_stack(
+            board_id, f"Target Stack {unique_suffix}", order=2
+        )
+        target_stack_data = {
+            "id": target_stack.id,
+            "title": target_stack.title,
+            "order": target_stack.order,
+        }
+        logger.info(f"Created target stack with ID: {target_stack.id}")
+
+        board_data = {
+            "id": board_id,
+            "title": board.title,
+            "color": board.color,
+        }
+
+        yield (board_data, source_stack_data, target_stack_data)
+
+    finally:
+        if board:
+            logger.info(f"Cleaning up board ID: {board.id}")
+            try:
+                await nc_client.deck.delete_board(board.id)
+            except Exception as e:
+                logger.warning(f"Error cleaning up board: {e}")
+
+
+async def test_reorder_card_move_to_different_stack(
+    nc_client: NextcloudClient, board_with_two_stacks: tuple
+):
+    """Test moving a card from one stack to another (issue #469).
+
+    This test reproduces the bug where the reorder_card API reports success
+    but the card doesn't actually move to the target stack.
+    """
+    board_data, source_stack_data, target_stack_data = board_with_two_stacks
+    board_id = board_data["id"]
+    source_stack_id = source_stack_data["id"]
+    target_stack_id = target_stack_data["id"]
+
+    # Create a card in the source stack
+    unique_suffix = uuid.uuid4().hex[:8]
+    card_title = f"Test Card {unique_suffix}"
+    card = await nc_client.deck.create_card(
+        board_id, source_stack_id, card_title, description="Card to be moved"
+    )
+    card_id = card.id
+    logger.info(f"Created card ID: {card_id} in source stack ID: {source_stack_id}")
+
+    try:
+        # Verify card is in source stack
+        card_before = await nc_client.deck.get_card(board_id, source_stack_id, card_id)
+        assert card_before.stackId == source_stack_id, (
+            f"Card should start in source stack {source_stack_id}, "
+            f"but is in {card_before.stackId}"
+        )
+        logger.info(f"Verified card is in source stack: {source_stack_id}")
+
+        # Move card to target stack
+        logger.info(
+            f"Moving card {card_id} from stack {source_stack_id} "
+            f"to stack {target_stack_id}"
+        )
+        await nc_client.deck.reorder_card(
+            board_id=board_id,
+            stack_id=source_stack_id,
+            card_id=card_id,
+            order=0,
+            target_stack_id=target_stack_id,
+        )
+        logger.info("reorder_card API call completed")
+
+        # Verify card moved to target stack
+        # Note: After moving, the card should be accessible from the target stack
+        card_after = await nc_client.deck.get_card(board_id, target_stack_id, card_id)
+        assert card_after.stackId == target_stack_id, (
+            f"Card should have moved to target stack {target_stack_id}, "
+            f"but is in {card_after.stackId}"
+        )
+        logger.info(f"SUCCESS: Card moved to target stack {target_stack_id}")
+
+    finally:
+        # Clean up - try to delete from target stack first, then source
+        try:
+            await nc_client.deck.delete_card(board_id, target_stack_id, card_id)
+        except Exception:
+            try:
+                await nc_client.deck.delete_card(board_id, source_stack_id, card_id)
+            except Exception as e:
+                logger.warning(f"Error cleaning up card: {e}")
+
+
+async def test_reorder_card_within_same_stack(
+    nc_client: NextcloudClient, board_with_two_stacks: tuple
+):
+    """Test reordering a card within the same stack (should work)."""
+    board_data, source_stack_data, _ = board_with_two_stacks
+    board_id = board_data["id"]
+    source_stack_id = source_stack_data["id"]
+
+    # Create two cards in the source stack
+    unique_suffix = uuid.uuid4().hex[:8]
+    card1 = await nc_client.deck.create_card(
+        board_id, source_stack_id, f"Card 1 {unique_suffix}", order=0
+    )
+    card2 = await nc_client.deck.create_card(
+        board_id, source_stack_id, f"Card 2 {unique_suffix}", order=1
+    )
+    logger.info(f"Created cards {card1.id} (order 0) and {card2.id} (order 1)")
+
+    try:
+        # Reorder card1 to position after card2
+        await nc_client.deck.reorder_card(
+            board_id=board_id,
+            stack_id=source_stack_id,
+            card_id=card1.id,
+            order=2,  # Move to position 2
+            target_stack_id=source_stack_id,  # Same stack
+        )
+        logger.info(f"Reordered card {card1.id} to order 2")
+
+        # Verify card is still in the same stack
+        card_after = await nc_client.deck.get_card(board_id, source_stack_id, card1.id)
+        assert card_after.stackId == source_stack_id
+        logger.info("Card reorder within same stack succeeded")
+
+    finally:
+        try:
+            await nc_client.deck.delete_card(board_id, source_stack_id, card1.id)
+            await nc_client.deck.delete_card(board_id, source_stack_id, card2.id)
+        except Exception as e:
+            logger.warning(f"Error cleaning up cards: {e}")

tests/integration/test_multi_user_basic_auth.py

@@ -0,0 +1,74 @@
+"""Integration tests for multi-user BasicAuth pass-through mode.
+
+Tests that BasicAuth credentials are extracted from request headers
+and passed through to Nextcloud APIs without storage (stateless).
+"""
+
+import json
+
+import pytest
+
+
+@pytest.mark.integration
+async def test_basic_auth_pass_through_notes_search(nc_mcp_basic_auth_client):
+    """Test BasicAuth pass-through with notes search tool."""
+    # Call tool - BasicAuth header is set at connection level by fixture
+    response = await nc_mcp_basic_auth_client.call_tool(
+        "nc_notes_search_notes", {"query": "test"}
+    )
+
+    # Verify tool executed successfully with pass-through auth
+    assert response is not None
+    assert not response.isError, f"Tool returned error: {response.content}"
+    # Response should have content with results
+    assert len(response.content) > 0
+    data = json.loads(response.content[0].text)
+    assert "results" in data
+
+
+@pytest.mark.integration
+async def test_basic_auth_pass_through_notes_create(nc_mcp_basic_auth_client):
+    """Test BasicAuth pass-through with notes create tool."""
+    # Create a note using BasicAuth
+    response = await nc_mcp_basic_auth_client.call_tool(
+        "nc_notes_create_note",
+        {
+            "title": "BasicAuth Test Note",
+            "content": "This note was created via BasicAuth pass-through",
+            "category": "Test",
+        },
+    )
+
+    assert response is not None
+    assert not response.isError, f"Tool returned error: {response.content}"
+    # Parse response and verify note was created
+    data = json.loads(response.content[0].text)
+    assert data.get("success") is True or "note_id" in data
+
+
+@pytest.mark.integration
+async def test_basic_auth_pass_through_get_note(nc_mcp_basic_auth_client):
+    """Test BasicAuth pass-through with get note tool."""
+    # First create a note to get
+    create_response = await nc_mcp_basic_auth_client.call_tool(
+        "nc_notes_create_note",
+        {
+            "title": "BasicAuth Get Test",
+            "content": "Note to retrieve",
+            "category": "Test",
+        },
+    )
+    assert not create_response.isError
+    create_data = json.loads(create_response.content[0].text)
+    note_id = create_data.get("id")
+
+    # Now get the note using BasicAuth
+    response = await nc_mcp_basic_auth_client.call_tool(
+        "nc_notes_get_note", {"note_id": note_id}
+    )
+
+    assert response is not None
+    assert not response.isError, f"Tool returned error: {response.content}"
+    data = json.loads(response.content[0].text)
+    # Nextcloud may append a number to duplicate titles
+    assert data.get("title", "").startswith("BasicAuth Get Test")

tests/integration/test_qdrant_collection_creation.py

@@ -10,12 +10,21 @@ These tests validate that:
 from unittest.mock import Mock
 
 import pytest
+from qdrant_client.models import VectorParams
 
 from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
 
 pytestmark = pytest.mark.integration
 
 
+def get_vector_params(collection_info) -> VectorParams:
+    """Get vector params from collection info, handling named vectors format."""
+    vectors = collection_info.config.params.vectors
+    if isinstance(vectors, dict):
+        return vectors["dense"]
+    return vectors
+
+
 @pytest.fixture(autouse=True)
 async def reset_singleton():
     """Reset the global Qdrant client singleton between tests."""
@@ -75,7 +84,7 @@ async def test_collection_auto_created_on_first_access(monkeypatch):
 
     # Verify collection has correct dimensions
     collection_info = await client.get_collection(collection_name)
-    assert collection_info.config.params.vectors.size == 384
+    assert get_vector_params(collection_info).size == 384
 
 
 @pytest.mark.integration
@@ -127,7 +136,7 @@ async def test_existing_collection_reused(monkeypatch):
 
     # Verify dimensions unchanged
     collection_info = await client2.get_collection(collection_name)
-    assert collection_info.config.params.vectors.size == 384
+    assert get_vector_params(collection_info).size == 384
 
 
 @pytest.mark.integration
@@ -164,7 +173,7 @@ async def test_dimension_mismatch_detected(monkeypatch, tmp_path):
 
     # Verify collection created
     collection_info = await client1.get_collection(collection_name)
-    assert collection_info.config.params.vectors.size == 384
+    assert get_vector_params(collection_info).size == 384
 
     # Close client1 to release file lock
     await client1.close()
@@ -248,12 +257,10 @@ async def test_collection_name_generation(monkeypatch):
     mock_settings = Settings(
         qdrant_location=":memory:",
         ollama_embedding_model="test-model",
+        otel_service_name="test-deployment",
         vector_sync_enabled=False,
     )
 
-    # Mock deployment ID
-    monkeypatch.setenv("MCP_DEPLOYMENT_ID", "test-deployment")
-
     monkeypatch.setattr(
         "nextcloud_mcp_server.vector.qdrant_client.get_settings", lambda: mock_settings
     )
@@ -319,4 +326,4 @@ async def test_collection_uses_cosine_distance(monkeypatch):
 
     from qdrant_client.models import Distance
 
-    assert collection_info.config.params.vectors.distance == Distance.COSINE
+    assert get_vector_params(collection_info).distance == Distance.COSINE

tests/integration/test_rag.py

@@ -51,6 +51,14 @@ logger = logging.getLogger(__name__)
 DEFAULT_MANUAL_PATH = "Nextcloud Manual.pdf"
 
 
+async def require_vector_sync_tools(nc_mcp_client):
+    """Skip test if vector sync tools are not available."""
+    tools = await nc_mcp_client.list_tools()
+    tool_names = [t.name for t in tools.tools]
+    if "nc_get_vector_sync_status" not in tool_names:
+        pytest.skip("Vector sync tools not available (VECTOR_SYNC_ENABLED not set)")
+
+
 async def llm_judge(
     provider: Provider,
     ground_truth: str,
@@ -116,6 +124,8 @@ async def indexed_manual_pdf(nc_client, nc_mcp_client):
     Environment Variables:
         RAG_MANUAL_PATH: Path to manual PDF in Nextcloud (default: Nextcloud Manual.pdf)
     """
+    await require_vector_sync_tools(nc_mcp_client)
+
     manual_path = os.getenv("RAG_MANUAL_PATH", DEFAULT_MANUAL_PATH)
 
     logger.info(f"Setting up indexed manual PDF: {manual_path}")
@@ -152,7 +162,7 @@ async def indexed_manual_pdf(nc_client, nc_mcp_client):
             )
 
             if not result.isError:
-                content = result.structuredContent or {}
+                content = json.loads(result.content[0].text) if result.content else {}
                 indexed = content.get("indexed_count", 0)
                 pending = content.get("pending_count", 1)
 
@@ -248,7 +258,7 @@ async def test_semantic_search_retrieval(
     )
 
     assert result.isError is False, f"Tool call failed: {result}"
-    data = result.structuredContent
+    data = json.loads(result.content[0].text)
 
     # Verify we got results
     assert data["success"] is True
@@ -295,7 +305,7 @@ async def test_semantic_search_answer_with_sampling(
     )
 
     assert result.isError is False, f"Tool call failed: {result}"
-    data = result.structuredContent
+    data = json.loads(result.content[0].text)
 
     # Verify response structure
     assert data["success"] is True
@@ -369,7 +379,7 @@ async def test_retrieval_quality_all_queries(
     )
 
     assert result.isError is False
-    data = result.structuredContent
+    data = json.loads(result.content[0].text)
 
     assert data["total_found"] >= min_expected_results, (
         f"Query '{query}' returned {data['total_found']} results, "
@@ -393,7 +403,7 @@ async def test_no_results_for_unrelated_query(nc_mcp_client, indexed_manual_pdf)
     )
 
     assert result.isError is False
-    data = result.structuredContent
+    data = json.loads(result.content[0].text)
 
     # Should have few or no high-scoring results
     # Low score threshold means we might get some results, but they should be low quality

tests/integration/test_sampling.py

@@ -13,14 +13,24 @@ Note: These tests require VECTOR_SYNC_ENABLED=true and a configured
 vector database with indexed test data.
 """
 
+import json
 from unittest.mock import MagicMock
 
+import anyio
 import pytest
 from mcp.types import CreateMessageResult, TextContent
 
 pytestmark = pytest.mark.integration
 
 
+async def require_vector_sync_tools(nc_mcp_client):
+    """Skip test if vector sync tools are not available."""
+    tools = await nc_mcp_client.list_tools()
+    tool_names = [t.name for t in tools.tools]
+    if "nc_get_vector_sync_status" not in tool_names:
+        pytest.skip("Vector sync tools not available (VECTOR_SYNC_ENABLED not set)")
+
+
 @pytest.fixture
 def mock_sampling_result():
     """Mock successful sampling result from MCP client."""
@@ -55,13 +65,14 @@ async def test_semantic_search_answer_successful_sampling(
     4. Mock ctx.session.create_message to return answer
     5. Verify response contains generated answer and sources
     """
+    await require_vector_sync_tools(nc_mcp_client)
+
     # Get initial indexed count before creating note
-    import asyncio
 
     initial_sync = await nc_mcp_client.call_tool(
         "nc_get_vector_sync_status", arguments={}
     )
-    initial_indexed_count = initial_sync.structuredContent["indexed_count"]
+    initial_indexed_count = json.loads(initial_sync.content[0].text)["indexed_count"]
     print(f"Initial indexed count: {initial_indexed_count}")
 
     # Create a note with content about Python async
@@ -90,7 +101,7 @@ Avoid blocking operations in async code.""",
         sync_status = await nc_mcp_client.call_tool(
             "nc_get_vector_sync_status", arguments={}
         )
-        status_data = sync_status.structuredContent
+        status_data = json.loads(sync_status.content[0].text)
 
         print(
             f"Sync status at {waited}s: indexed={status_data['indexed_count']}, pending={status_data['pending_count']}, status={status_data['status']}"
@@ -107,7 +118,7 @@ Avoid blocking operations in async code.""",
             )
             break
 
-        await asyncio.sleep(wait_interval)
+        await anyio.sleep(wait_interval)
         waited += wait_interval
 
     # Verify sync completed
@@ -135,7 +146,7 @@ Avoid blocking operations in async code.""",
     assert call_result.isError is False, (
         f"Tool call failed: {call_result.content[0].text if call_result.isError else ''}"
     )
-    result = call_result.structuredContent
+    result = json.loads(call_result.content[0].text)
 
     # Verify response structure
     assert result is not None
@@ -179,6 +190,8 @@ async def test_semantic_search_answer_no_results(nc_mcp_client):
     2. Verify response indicates no documents found
     3. Verify no sampling call was made (no sources to base answer on)
     """
+    await require_vector_sync_tools(nc_mcp_client)
+
     call_result = await nc_mcp_client.call_tool(
         "nc_semantic_search_answer",
         arguments={
@@ -192,7 +205,7 @@ async def test_semantic_search_answer_no_results(nc_mcp_client):
     assert call_result.isError is False, (
         f"Tool call failed: {call_result.content[0].text if call_result.isError else ''}"
     )
-    result = call_result.structuredContent
+    result = json.loads(call_result.content[0].text)
 
     # Should get "no documents found" message
     assert result is not None
@@ -214,6 +227,8 @@ async def test_semantic_search_answer_with_limit(nc_mcp_client, temporary_note_f
     3. Query with limit=2
     4. Verify at most 2 sources in response
     """
+    await require_vector_sync_tools(nc_mcp_client)
+
     # Create multiple related notes
     _note1 = await temporary_note_factory(
         title="Python Async Part 1",
@@ -232,7 +247,6 @@ async def test_semantic_search_answer_with_limit(nc_mcp_client, temporary_note_f
     )
 
     # Wait for vector indexing to complete
-    import asyncio
 
     max_wait = 30
     wait_interval = 1
@@ -242,12 +256,12 @@ async def test_semantic_search_answer_with_limit(nc_mcp_client, temporary_note_f
         sync_status = await nc_mcp_client.call_tool(
             "nc_get_vector_sync_status", arguments={}
         )
-        status_data = sync_status.structuredContent
+        status_data = json.loads(sync_status.content[0].text)
 
         if status_data["status"] == "idle" and status_data["pending_count"] == 0:
             break
 
-        await asyncio.sleep(wait_interval)
+        await anyio.sleep(wait_interval)
         waited += wait_interval
 
     assert waited < max_wait, f"Vector sync did not complete within {max_wait} seconds"
@@ -265,7 +279,7 @@ async def test_semantic_search_answer_with_limit(nc_mcp_client, temporary_note_f
     assert call_result.isError is False, (
         f"Tool call failed: {call_result.content[0].text if call_result.isError else ''}"
     )
-    result = call_result.structuredContent
+    result = json.loads(call_result.content[0].text)
 
     # Should respect limit
     assert len(result["sources"]) <= 2
@@ -282,6 +296,8 @@ async def test_semantic_search_answer_score_threshold(
     3. Query with high threshold (0.9)
     4. Verify only high-scoring results returned
     """
+    await require_vector_sync_tools(nc_mcp_client)
+
     _note = await temporary_note_factory(
         title="Exact Match Test",
         content="This is a very specific test document about widget manufacturing",
@@ -289,7 +305,6 @@ async def test_semantic_search_answer_score_threshold(
     )
 
     # Wait for vector indexing to complete
-    import asyncio
 
     max_wait = 30
     wait_interval = 1
@@ -299,12 +314,12 @@ async def test_semantic_search_answer_score_threshold(
         sync_status = await nc_mcp_client.call_tool(
             "nc_get_vector_sync_status", arguments={}
         )
-        status_data = sync_status.structuredContent
+        status_data = json.loads(sync_status.content[0].text)
 
         if status_data["status"] == "idle" and status_data["pending_count"] == 0:
             break
 
-        await asyncio.sleep(wait_interval)
+        await anyio.sleep(wait_interval)
         waited += wait_interval
 
     assert waited < max_wait, f"Vector sync did not complete within {max_wait} seconds"
@@ -323,7 +338,7 @@ async def test_semantic_search_answer_score_threshold(
     assert call_result.isError is False, (
         f"Tool call failed: {call_result.content[0].text if call_result.isError else ''}"
     )
-    result = call_result.structuredContent
+    result = json.loads(call_result.content[0].text)
 
     # Note: Semantic search scores depend on embedding model
     # We just verify the tool accepts the parameter
@@ -345,6 +360,8 @@ async def test_semantic_search_answer_max_tokens(nc_mcp_client, temporary_note_f
     Note: Token limiting is enforced by the MCP client's LLM, not the server.
     This test just verifies the parameter is correctly passed.
     """
+    await require_vector_sync_tools(nc_mcp_client)
+
     _note = await temporary_note_factory(
         title="Long Document",
         content="This is a document with lots of content. " * 50,
@@ -352,7 +369,6 @@ async def test_semantic_search_answer_max_tokens(nc_mcp_client, temporary_note_f
     )
 
     # Wait for vector indexing to complete
-    import asyncio
 
     max_wait = 30
     wait_interval = 1
@@ -362,12 +378,12 @@ async def test_semantic_search_answer_max_tokens(nc_mcp_client, temporary_note_f
         sync_status = await nc_mcp_client.call_tool(
             "nc_get_vector_sync_status", arguments={}
         )
-        status_data = sync_status.structuredContent
+        status_data = json.loads(sync_status.content[0].text)
 
         if status_data["status"] == "idle" and status_data["pending_count"] == 0:
             break
 
-        await asyncio.sleep(wait_interval)
+        await anyio.sleep(wait_interval)
         waited += wait_interval
 
     assert waited < max_wait, f"Vector sync did not complete within {max_wait} seconds"
@@ -386,7 +402,7 @@ async def test_semantic_search_answer_max_tokens(nc_mcp_client, temporary_note_f
     assert call_result.isError is False, (
         f"Tool call failed: {call_result.content[0].text if call_result.isError else ''}"
     )
-    result = call_result.structuredContent
+    result = json.loads(call_result.content[0].text)
 
     # Should not error, even if sampling fails
     assert result is not None

tests/integration/test_semantic_search.py

@@ -10,6 +10,7 @@ Uses SimpleEmbeddingProvider for deterministic, in-process embeddings
 without requiring external services like Ollama.
 """
 
+import math
 import tempfile
 from pathlib import Path
 
@@ -147,7 +148,6 @@ async def test_simple_embedding_provider_deterministic(simple_embedding_provider
     assert len(embedding1) == 384
 
     # Should be normalized (unit length)
-    import math
 
     norm = math.sqrt(sum(x * x for x in embedding1))
     assert abs(norm - 1.0) < 1e-6
@@ -340,7 +340,6 @@ async def test_batch_embedding(simple_embedding_provider: SimpleEmbeddingProvide
     assert all(len(emb) == 384 for emb in embeddings)
 
     # Each should be normalized
-    import math
 
     for emb in embeddings:
         norm = math.sqrt(sum(x * x for x in emb))

tests/load/oauth_metrics.py

@@ -6,6 +6,7 @@ workflow completion rates, and cross-user operation latencies.
 """
 
 import statistics
+import time
 from collections import Counter, defaultdict
 from typing import Any
 
@@ -44,13 +45,11 @@ class OAuthBenchmarkMetrics:
 
     def start(self):
         """Mark the start of the benchmark."""
-        import time
 
         self.start_time = time.time()
 
     def stop(self):
         """Mark the end of the benchmark."""
-        import time
 
         self.end_time = time.time()
 

tests/load/oauth_pool.py

@@ -5,8 +5,12 @@ Manages multiple OAuth-authenticated users for realistic multi-user load testing
 """
 
 import logging
+import secrets
+import string
+import time
 from dataclasses import dataclass
 from typing import Any
+from urllib.parse import quote
 
 import anyio
 import httpx
@@ -333,8 +337,6 @@ class OAuthUserPool:
             TimeoutError: If callback not received within timeout
             ValueError: If token exchange fails
         """
-        import time
-        from urllib.parse import quote
 
         logger.info(f"Starting Playwright OAuth flow for {username}...")
         logger.debug(f"Using state: {state[:16]}...")
@@ -478,8 +480,6 @@ class UserSessionWrapper:
 
 def generate_secure_password(length: int = 20) -> str:
     """Generate a secure random password."""
-    import secrets
-    import string
 
     alphabet = string.ascii_letters + string.digits + "!@#$%^&*()"
     return "".join(secrets.choice(alphabet) for _ in range(length))

tests/load/workloads.py

@@ -4,6 +4,7 @@ Workload definitions for load testing the MCP server.
 Defines realistic operation mixes and individual operation functions.
 """
 
+import json
 import logging
 import random
 import time
@@ -91,8 +92,6 @@ class WorkloadOperations:
             if result and len(result.content) > 0:
                 content = result.content[0]
                 if hasattr(content, "text"):
-                    import json
-
                     note_data = json.loads(content.text)
                     note_id = note_data.get("id")
                     if note_id:
@@ -222,8 +221,6 @@ class MixedWorkload:
                         "nc_notes_get_note", {"note_id": note_id}
                     )
                     if get_result and len(get_result.content) > 0:
-                        import json
-
                         note_data = json.loads(get_result.content[0].text)
                         etag = note_data.get("etag", "")
                         self._warmup_note_ids.append((note_id, etag))

tests/manual/test_nextcloud_impersonate.py

@@ -18,6 +18,7 @@ Usage:
 import asyncio
 import logging
 import os
+import re
 import sys
 
 # Add parent directory to path
@@ -127,7 +128,6 @@ async def main():
         )
 
         # Extract requesttoken from HTML
-        import re
 
         token_match = re.search(r'data-requesttoken="([^"]+)"', settings_response.text)
         if token_match:

tests/server/oauth/test_astrolabe_multi_server_integration.py

@@ -0,0 +1,104 @@
+"""Test Astrolabe integration with multiple MCP server deployments.
+
+This test suite verifies that the Astrolabe app can be dynamically configured
+to connect to different MCP server deployments (mcp-oauth, mcp-keycloak, etc.).
+
+The configuration is managed dynamically during tests using the
+configure_astrolabe_for_mcp_server fixture, which allows testing multiple
+deployment scenarios without requiring static post-installation configuration.
+"""
+
+import logging
+
+import pytest
+
+logger = logging.getLogger(__name__)
+
+pytestmark = [pytest.mark.integration, pytest.mark.oauth]
+
+
+class TestAstrolabeMultiServerIntegration:
+    """Test suite for Astrolabe integration with multiple MCP servers."""
+
+    @pytest.mark.parametrize(
+        "mcp_server_config",
+        [
+            {
+                "name": "mcp-oauth",
+                "internal_url": "http://mcp-oauth:8001",
+                "public_url": "http://localhost:8001",
+            },
+            {
+                "name": "mcp-keycloak",
+                "internal_url": "http://mcp-keycloak:8002",
+                "public_url": "http://localhost:8002",
+            },
+            # Add more MCP server configurations as needed:
+            # {
+            #     "name": "mcp-multi-user-basic",
+            #     "internal_url": "http://mcp-multi-user-basic:8000",
+            #     "public_url": "http://localhost:8003",
+            # },
+        ],
+    )
+    async def test_astrolabe_configuration_for_different_servers(
+        self, configure_astrolabe_for_mcp_server, mcp_server_config
+    ):
+        """Test that Astrolabe can be configured for different MCP servers.
+
+        This test verifies that:
+        1. The configure_astrolabe_for_mcp_server fixture successfully configures
+           the Astrolabe app for different MCP server endpoints
+        2. OAuth client credentials are properly generated and stored
+        3. The configuration can be dynamically changed between tests
+        """
+        logger.info(f"Configuring Astrolabe for {mcp_server_config['name']}...")
+
+        # Configure Astrolabe for the specific MCP server
+        credentials = await configure_astrolabe_for_mcp_server(
+            mcp_server_internal_url=mcp_server_config["internal_url"],
+            mcp_server_public_url=mcp_server_config["public_url"],
+        )
+
+        # Verify credentials were returned
+        assert "client_id" in credentials
+        assert "client_secret" in credentials
+        assert credentials["client_id"] == "nextcloudMcpServerUIPublicClient"
+        assert len(credentials["client_secret"]) > 0
+
+        logger.info(
+            f"✓ Astrolabe successfully configured for {mcp_server_config['name']}"
+        )
+        logger.info(f"  Internal URL: {mcp_server_config['internal_url']}")
+        logger.info(f"  Public URL: {mcp_server_config['public_url']}")
+        logger.info(f"  Client ID: {credentials['client_id']}")
+        logger.info(f"  Client Secret: {credentials['client_secret'][:8]}...")
+
+    async def test_astrolabe_reconfiguration(self, configure_astrolabe_for_mcp_server):
+        """Test that Astrolabe can be reconfigured multiple times in the same session.
+
+        This verifies that the OAuth client can be recreated with different
+        settings without conflicts.
+        """
+        # First configuration: mcp-oauth
+        logger.info("First configuration: mcp-oauth")
+        credentials1 = await configure_astrolabe_for_mcp_server(
+            mcp_server_internal_url="http://mcp-oauth:8001",
+            mcp_server_public_url="http://localhost:8001",
+        )
+
+        assert credentials1["client_id"] == "nextcloudMcpServerUIPublicClient"
+
+        # Second configuration: mcp-keycloak (reconfiguration)
+        logger.info("Second configuration: mcp-keycloak (reconfiguration)")
+        credentials2 = await configure_astrolabe_for_mcp_server(
+            mcp_server_internal_url="http://mcp-keycloak:8002",
+            mcp_server_public_url="http://localhost:8002",
+        )
+
+        assert credentials2["client_id"] == "nextcloudMcpServerUIPublicClient"
+
+        # Client secrets should be different (new client created)
+        assert credentials1["client_secret"] != credentials2["client_secret"]
+
+        logger.info("✓ Astrolabe successfully reconfigured without conflicts")

tests/server/oauth/test_keycloak_dcr.py

@@ -17,6 +17,7 @@ Architecture:
     MCP Client → Keycloak DCR → Keycloak OAuth → MCP Server → Nextcloud APIs
 """
 
+import json
 import logging
 import os
 import secrets
@@ -623,7 +624,6 @@ async def test_keycloak_dcr_architecture():
     }
 
     logger.info("Keycloak DCR Architecture:")
-    import json
 
     logger.info(json.dumps(architecture, indent=2))
 

tests/server/oauth/test_nc_php_app_debug.py

@@ -10,8 +10,14 @@ logger = logging.getLogger(__name__)
 pytestmark = [pytest.mark.integration, pytest.mark.oauth]
 
 
-async def test_capture_settings_page(browser):
+async def test_capture_settings_page(browser, configure_astrolabe_for_mcp_server):
     """Capture what's actually rendered on the personal settings page."""
+    # Configure Astrolabe for mcp-oauth server
+    await configure_astrolabe_for_mcp_server(
+        mcp_server_internal_url="http://mcp-oauth:8001",
+        mcp_server_public_url="http://localhost:8001",
+    )
+
     nextcloud_host = os.getenv("NEXTCLOUD_HOST", "http://localhost:8080")
     username = os.getenv("NEXTCLOUD_USERNAME", "admin")
     password = os.getenv("NEXTCLOUD_PASSWORD", "admin")
@@ -31,7 +37,7 @@ async def test_capture_settings_page(browser):
 
         # Navigate to settings
         logger.info("Navigating to personal MCP settings...")
-        await page.goto(f"{nextcloud_host}/settings/user/mcp")
+        await page.goto(f"{nextcloud_host}/settings/user/astrolabe")
         await page.wait_for_load_state("networkidle")
 
         # Capture page content
@@ -46,13 +52,13 @@ async def test_capture_settings_page(browser):
         logger.info(f"Page URL: {page.url}")
         logger.info(f"Page title: {await page.title()}")
 
-        # Check for key strings
+        # Check for key strings (Vue 3 UI)
         checks = [
-            "Authorize Access",
-            "Authorization Required",
-            "MCP Server",
-            "Sign In Again",
-            "astrolabe",
+            "Enable Semantic Search",  # oauth-required.php authorization button
+            "Service Status",  # personal.php when authorized
+            "Background Sync Access",  # personal.php when authorized
+            "What happens next?",  # oauth-required.php steps
+            "Astrolabe",  # Header
         ]
 
         for check in checks:
@@ -69,6 +75,15 @@ async def test_capture_settings_page(browser):
         for i, link_text in enumerate(links[:10]):
             logger.info(f"  Link {i}: {link_text}")
 
+        # Check the Enable Semantic Search button href
+        try:
+            btn = page.locator('a:has-text("Enable Semantic Search")')
+            if await btn.count() > 0:
+                href = await btn.get_attribute("href")
+                logger.info(f"Enable Semantic Search button href: {href}")
+        except Exception as e:
+            logger.warning(f"Could not get button href: {e}")
+
         # Check for error messages
         if "error" in page_content.lower():
             logger.warning("Page contains 'error' keyword")

tests/server/oauth/test_nc_php_app_oauth.py

@@ -44,14 +44,32 @@ async def nc_admin_http_client(nextcloud_credentials):
 
 
 @pytest.fixture(scope="module")
-async def authorized_nc_session(browser, nextcloud_credentials):
+async def configure_astrolabe_for_tests(configure_astrolabe_for_mcp_server):
+    """Configure Astrolabe to connect to mcp-oauth server before running tests.
+
+    This module-scoped fixture ensures Astrolabe is properly configured
+    for the mcp-oauth server (http://localhost:8001) before any tests run.
+    """
+    logger.info("Configuring Astrolabe for mcp-oauth server...")
+    await configure_astrolabe_for_mcp_server(
+        mcp_server_internal_url="http://mcp-oauth:8001",
+        mcp_server_public_url="http://localhost:8001",
+    )
+    logger.info("✓ Astrolabe configured for mcp-oauth server")
+
+
+@pytest.fixture(scope="module")
+async def authorized_nc_session(
+    browser, nextcloud_credentials, configure_astrolabe_for_tests
+):
     """Module-scoped fixture that logs in and authorizes the NC PHP app once.
 
     This fixture:
-    1. Creates a browser context
-    2. Logs in to Nextcloud
-    3. Authorizes the MCP Server UI app (if not already authorized)
-    4. Returns the page for use in all tests
+    1. Configures Astrolabe for mcp-oauth server (via configure_astrolabe_for_tests)
+    2. Creates a browser context
+    3. Logs in to Nextcloud
+    4. Authorizes the MCP Server UI app (if not already authorized)
+    5. Returns the page for use in all tests
 
     The authorization is done once and reused for all tests in this module.
     """
@@ -87,21 +105,26 @@ async def authorized_nc_session(browser, nextcloud_credentials):
 
         # Step 2: Navigate to personal MCP settings
         logger.info("Navigating to personal MCP settings...")
-        await page.goto(f"{host}/settings/user/mcp")
+        await page.goto(f"{host}/settings/user/astrolabe")
         await page.wait_for_load_state("networkidle")
 
         page_content = await page.content()
 
         # Step 3: Check if authorization is needed
-        if "Authorize Access" in page_content or "authorize" in page_content.lower():
+        # Vue 3 UI shows "Enable Semantic Search" when not authorized
+        if (
+            "Enable Semantic Search" in page_content
+            or "What happens next?" in page_content
+        ):
             logger.info("User not authorized yet - initiating OAuth flow...")
 
-            # Click "Authorize Access" button
+            # Click "Enable Semantic Search" button (Vue 3 template text)
             authorize_selectors = [
-                'button:has-text("Authorize")',
-                'a:has-text("Authorize")',
-                '[href*="oauth/authorize"]',
-                'button:has-text("Connect")',
+                'a:has-text("Enable Semantic Search")',
+                'button:has-text("Enable Semantic Search")',
+                'a:has-text("Sign In Again")',
+                "a.button.primary",
+                '[href*="oauth/login"]',
             ]
 
             clicked = False
@@ -124,9 +147,17 @@ async def authorized_nc_session(browser, nextcloud_credentials):
             # Wait for page to load after clicking
             await page.wait_for_load_state("networkidle", timeout=10000)
             current_url = page.url
+            logger.info(f"After clicking authorize, current URL: {current_url}")
+
+            # Take screenshot for debugging
+            await page.screenshot(path="/tmp/nc-php-app-after-authorize-click.png")
+            logger.info("Screenshot saved to /tmp/nc-php-app-after-authorize-click.png")
 
             # Handle OAuth consent if needed
-            if "/apps/oidc/authorize" in current_url:
+            if (
+                "/apps/oidc/authorize" in current_url
+                or "/apps/oidc/consent" in current_url
+            ):
                 logger.info("On OIDC authorization page - granting consent...")
 
                 consent_selectors = [
@@ -145,7 +176,7 @@ async def authorized_nc_session(browser, nextcloud_credentials):
                         continue
 
             # Wait for redirect back to settings
-            await page.wait_for_url(f"{host}/settings/user/mcp", timeout=15000)
+            await page.wait_for_url(f"{host}/settings/user/astrolabe", timeout=15000)
             await page.wait_for_load_state("networkidle")
             logger.info("✓ OAuth authorization completed")
 
@@ -179,28 +210,32 @@ class TestNcPhpAppOAuth:
         host = authorized_nc_session["host"]
 
         # Navigate to settings (may already be there)
-        await page.goto(f"{host}/settings/user/mcp")
+        await page.goto(f"{host}/settings/user/astrolabe")
         await page.wait_for_load_state("networkidle")
 
         page_content = await page.content()
 
-        # Look for indicators that authorization succeeded
+        # Look for indicators that authorization succeeded (Vue 3 personal.php template)
+        # These must be unique to the authorized state (not found in oauth-required.php)
         success_indicators = [
-            "Connected",
-            "Disconnect",
-            "Server Connection",
-            "Session Information",
-            "MCP Server",
+            "Service Status",
+            "Background Sync Access",
+            "Manage Connection",
+            "Revoke Access",
+            "Service URL",
         ]
 
-        has_success_indicator = any(
-            indicator in page_content for indicator in success_indicators
-        )
+        found_indicators = [ind for ind in success_indicators if ind in page_content]
+        has_success_indicator = len(found_indicators) > 0
+
+        # Always take screenshot for debugging
+        screenshot_path = "/tmp/nc-php-app-auth-check.png"
+        await page.screenshot(path=screenshot_path)
+        logger.info(f"Authorization check screenshot: {screenshot_path}")
+        logger.info(f"Found success indicators: {found_indicators}")
 
         if not has_success_indicator:
-            screenshot_path = "/tmp/nc-php-app-auth-check.png"
-            await page.screenshot(path=screenshot_path)
-            logger.error(f"Authorization check failed. Screenshot: {screenshot_path}")
+            logger.error("Authorization check failed.")
 
         assert has_success_indicator, "Settings page should show user is authorized"
         logger.info("✓ Authorization verification passed")
@@ -214,7 +249,7 @@ class TestNcPhpAppOAuth:
         page = authorized_nc_session["page"]
         host = authorized_nc_session["host"]
 
-        await page.goto(f"{host}/settings/user/mcp")
+        await page.goto(f"{host}/settings/user/astrolabe")
         await page.wait_for_load_state("networkidle")
 
         page_content = await page.content()
@@ -225,12 +260,12 @@ class TestNcPhpAppOAuth:
         logger.info(f"Screenshot saved: {screenshot_path}")
         logger.info(f"Page content excerpt: {page_content[:1000]}")
 
-        # Verify session information is visible - these are the actual labels from template
+        # Verify session information is visible (Vue 3 personal.php template)
         session_indicators = [
-            "Server Connection",
-            "Session Information",
-            "Connection Management",
-            "MCP Server",
+            "Service Status",
+            "Service URL",
+            "Version",
+            "Background Sync Access",
         ]
 
         found_indicators = [ind for ind in session_indicators if ind in page_content]
@@ -252,17 +287,17 @@ class TestNcPhpAppOAuth:
         host = authorized_nc_session["host"]
 
         # Check personal settings page shows server status
-        await page.goto(f"{host}/settings/user/mcp")
+        await page.goto(f"{host}/settings/user/astrolabe")
         await page.wait_for_load_state("networkidle")
 
         page_content = await page.content()
 
-        # Look for data that comes from management API or template structure
+        # Look for data that comes from management API or template structure (Vue 3)
         api_indicators = [
-            "Server Connection",  # Section header
-            "Server URL",  # Server info
-            "Connection Management",  # Connection section
-            "Vector Visualization",  # Vector sync section
+            "Service Status",  # Section header
+            "Service URL",  # Server info from API
+            "Version",  # Server version from management API
+            "Semantic Search",  # Vector sync status
         ]
 
         found_api_data = [ind for ind in api_indicators if ind in page_content]
@@ -280,23 +315,24 @@ class TestNcPhpAppOAuth:
         page = authorized_nc_session["page"]
         host = authorized_nc_session["host"]
 
-        await page.goto(f"{host}/settings/admin/mcp")
+        await page.goto(f"{host}/settings/admin/astrolabe")
         await page.wait_for_load_state("networkidle")
 
         page_content = await page.content()
 
-        # Admin page should show server status
+        # Admin page should show server status (Vue 3 AdminSettings.vue)
         admin_indicators = [
-            "MCP Server",
-            "Server Status",
+            "Astrolabe",
+            "Service Status",
             "Version",
+            "Semantic Search",
         ]
 
         found_indicators = [ind for ind in admin_indicators if ind in page_content]
 
-        # Admin page should at least show the MCP Server header
-        assert "MCP Server" in page_content or "mcp" in page_content.lower(), (
-            "Admin settings page should show MCP Server section"
+        # Admin page should at least show the Astrolabe header or Service Status
+        assert "Astrolabe" in page_content or "Service Status" in page_content, (
+            "Admin settings page should show Astrolabe section"
         )
 
         logger.info(f"✓ Admin settings page verified - found: {found_indicators}")
@@ -337,13 +373,13 @@ class TestNcPhpAppDisconnect:
             await page.wait_for_url(f"{host}/apps/dashboard/", timeout=10000)
 
             # Navigate to personal settings
-            await page.goto(f"{host}/settings/user/mcp")
+            await page.goto(f"{host}/settings/user/astrolabe")
             await page.wait_for_load_state("networkidle")
 
             page_content = await page.content()
 
-            # Check if user is authorized
-            if "Disconnect" not in page_content:
+            # Check if user is authorized (Vue 3 personal.php shows Disconnect/Revoke when authorized)
+            if "Disconnect" not in page_content and "Revoke Access" not in page_content:
                 pytest.skip("User not authorized - cannot test disconnect")
 
             # Click disconnect button
@@ -366,10 +402,10 @@ class TestNcPhpAppDisconnect:
             # Wait for page reload
             await page.wait_for_load_state("networkidle")
 
-            # Verify we're back to "Authorize Access" state
+            # Verify we're back to "Enable Semantic Search" state (Vue 3 oauth-required.php)
             page_content = await page.content()
-            assert "Authorize" in page_content, (
-                "Settings page should show 'Authorize Access' after disconnect"
+            assert "Enable Semantic Search" in page_content, (
+                "Settings page should show 'Enable Semantic Search' after disconnect"
             )
 
             logger.info("✓ Disconnect flow test passed")

tests/server/oauth/test_scope_authorization.py

@@ -11,13 +11,15 @@ Note: Tests use JWT OAuth tokens because scopes are embedded in the token payloa
 enabling efficient scope-based tool filtering without additional API calls.
 """
 
+import logging
+
+import httpx
 import pytest
 
 
 @pytest.mark.integration
 async def test_prm_endpoint():
     """Test that the Protected Resource Metadata endpoint returns correct data."""
-    import httpx
 
     # Test the PRM endpoint directly (RFC 9728 - path includes /mcp resource)
     async with httpx.AsyncClient() as client:
@@ -60,7 +62,6 @@ async def test_basicauth_shows_all_tools(nc_mcp_client):
 @pytest.mark.integration
 async def test_read_only_token_filters_write_tools(nc_mcp_oauth_client_read_only):
     """Test that a token with only read scopes filters out write tools."""
-    import logging
 
     logger = logging.getLogger(__name__)
 
@@ -109,7 +110,6 @@ async def test_read_only_token_filters_write_tools(nc_mcp_oauth_client_read_only
 @pytest.mark.integration
 async def test_write_only_token_filters_read_tools(nc_mcp_oauth_client_write_only):
     """Test that a token with only write scopes filters out read tools."""
-    import logging
 
     logger = logging.getLogger(__name__)
 
@@ -158,7 +158,6 @@ async def test_write_only_token_filters_read_tools(nc_mcp_oauth_client_write_onl
 @pytest.mark.integration
 async def test_full_access_token_shows_all_tools(nc_mcp_oauth_client_full_access):
     """Test that a token with both read and write scopes scopes can see all tools."""
-    import logging
 
     logger = logging.getLogger(__name__)
 
@@ -402,7 +401,6 @@ async def test_jwt_with_no_custom_scopes_returns_zero_tools(
     - OAuth provisioning tools (requiring only 'openid') remain visible
       so users can provision Nextcloud access after authentication
     """
-    import logging
 
     logger = logging.getLogger(__name__)
 
@@ -442,7 +440,6 @@ async def test_jwt_consent_scenarios_read_only(nc_mcp_oauth_client_read_only):
     Simulates user granting only read permission during OAuth consent.
     Expected: Should see read tools but not write tools.
     """
-    import logging
 
     logger = logging.getLogger(__name__)
 
@@ -480,7 +477,6 @@ async def test_jwt_consent_scenarios_write_only(nc_mcp_oauth_client_write_only):
     Simulates user granting only write permission during OAuth consent.
     Expected: Should see write tools but not read-only tools.
     """
-    import logging
 
     logger = logging.getLogger(__name__)
 
@@ -518,7 +514,6 @@ async def test_jwt_consent_scenarios_full_access(nc_mcp_oauth_client_full_access
     Simulates user granting both permissions during OAuth consent.
     Expected: Should see all 90+ tools (both read and write).
     """
-    import logging
 
     logger = logging.getLogger(__name__)
 

tests/server/oauth/test_token_exchange.py

@@ -6,10 +6,12 @@ Tests the critical token exchange pattern that separates:
 """
 
 import os
+import tempfile
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import jwt
 import pytest
+from cryptography.fernet import Fernet
 
 from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
@@ -21,9 +23,6 @@ pytestmark = pytest.mark.unit
 @pytest.fixture
 async def token_storage():
     """Create test token storage."""
-    import tempfile
-
-    from cryptography.fernet import Fernet
 
     # Generate valid Fernet key
     encryption_key = Fernet.generate_key()