fix: return all notes when search query is empty

Previously, an empty query string to nc_notes_search_notes would return zero results due to an early return when no query tokens were present. This was counterintuitive - users expect an empty query to list all notes, not return nothing. Changes: - Modified NotesSearchController.search_notes() to return all notes when query is empty - Added documentation to clarify this behavior - Empty query results have _score: None (no relevance scoring) - Non-empty query results continue to have relevance scores Fixes behavior where listing all notes was impossible via the search tool. 🤖 Generated with [Claude Code](https://claude.com/claude-code) Co-Authored-By: Claude <noreply@anthropic.com>
feat: Complete Phase 5 - Instrument all 93 MCP tools
2025-11-13 21:57:14 +01:00 · 2025-11-13 16:58:44 +01:00 · 2025-11-13 16:40:56 +01:00 · 2025-11-13 16:23:00 +01:00 · 2025-11-13 16:14:38 +01:00 · 2025-11-13 12:10:42 +00:00
71 changed files with 8107 additions and 2223 deletions
@@ -20,7 +20,7 @@ jobs:
      - name: Checkout
        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5
      - name: Install uv
-        uses: astral-sh/setup-uv@85856786d1ce8acfbcc2f13a5f3fbd6b938f9f41 # v7.1.2
+        uses: astral-sh/setup-uv@5a7eac68fb9809dea845d802897dc5c723910fa3 # v7.1.3
      - name: Install Python 3.11
        run: uv python install 3.11
      - name: Build
@@ -11,7 +11,7 @@ jobs:
    steps:
      - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
      - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@85856786d1ce8acfbcc2f13a5f3fbd6b938f9f41 # v7.1.2
+        uses: astral-sh/setup-uv@5a7eac68fb9809dea845d802897dc5c723910fa3 # v7.1.3
      - name: Check format
        run: |
          uv run --frozen ruff format --diff
@@ -56,7 +56,7 @@ jobs:
          up-flags: "--build"

      - name: Install the latest version of uv
-        uses: astral-sh/setup-uv@85856786d1ce8acfbcc2f13a5f3fbd6b938f9f41 # v7.1.2
+        uses: astral-sh/setup-uv@5a7eac68fb9809dea845d802897dc5c723910fa3 # v7.1.3

      - name: Install Playwright dependencies
        run: |
@@ -5,5 +5,11 @@ __pycache__/
 .env.local
 .env.*.local

+# Git
+worktrees/
+
+docker-compose.override.yml
+
 # Generated by pytest used to login users
 .nextcloud_oauth_*.json
+.playwright-mcp/
@@ -1,3 +1,74 @@
+## v0.33.1 (2025-11-13)
+
+### Fix
+
+- Move grafana_folder from labels to annotations
+
+## v0.33.0 (2025-11-13)
+
+### Feat
+
+- Add Grafana dashboard and vector sync metric instrumentation
+
+## v0.32.1 (2025-11-12)
+
+### Fix
+
+- add dynamic dimension detection for Ollama embedding models
+
+## v0.32.0 (2025-11-11)
+
+### Feat
+
+- **ollama**: Pull model on startup if not available in ollama
+- add dynamic vector sync status updates with htmx polling
+- add webhook management UI and BeforeNodeDeletedEvent support
+- validate Nextcloud webhook schemas and document findings
+
+### Fix
+
+- improve webapp tab UI with CSS Grid and viewport-filling container
+
+### Refactor
+
+- move webapp from /user/page to /app
+- consolidate database storage for webhooks and OAuth tokens
+
+## v0.31.1 (2025-11-10)
+
+### Refactor
+
+- simplify OpenTelemetry tracing configuration
+
+## v0.31.0 (2025-11-10)
+
+### Feat
+
+- skip tracing for health and metrics endpoints
+
+### Fix
+
+- add retry logic for ETag conflicts in category change test
+- optimize Notes API pagination with pruneBefore parameter
+
+## v0.30.0 (2025-11-10)
+
+### Feat
+
+- **helm**: Add document chunking configuration
+- **vector**: Add configurable chunk size and overlap for document embedding
+- **vector**: Support multiple embedding models with auto-generated collection names
+
+### Fix
+
+- Support in-memory Qdrant for CI testing
+
+## v0.29.2 (2025-11-09)
+
+### Fix
+
+- **helm**: Set default strategy to Recreate
+
 ## v0.29.1 (2025-11-09)

 ### Fix
@@ -51,7 +122,7 @@
 - implement ADR-009 - refactor semantic search to use generic semantic:read scope
 - implement MCP sampling for semantic search RAG (ADR-008)
 - add optional vector database and semantic search to helm chart
- add vector sync processing status to /user/page endpoint
+- add vector sync processing status to /app endpoint
 - implement semantic search tool and fix vector sync issues (ADR-007 Phase 3)
 - implement vector sync scanner and processor (ADR-007 Phase 2)

@@ -1,4 +1,4 @@
-FROM ghcr.io/astral-sh/uv:0.9.8-python3.11-alpine@sha256:6c842c49ad032f46b62f32a7e7779f45f12671a8e0d82ea24c766ab62d58b396
+FROM ghcr.io/astral-sh/uv:0.9.9-python3.11-alpine@sha256:0faa7934fac1db7f5056f159c1224d144bab864fd2677a4066d25a686ae32edd

 # Install dependencies
 # 1. git (required for caldav dependency from git)
@@ -9,7 +9,7 @@ WORKDIR /app

 COPY . .

-RUN uv sync --locked --no-dev
+RUN uv sync --locked --no-dev --no-editable

 ENV PYTHONUNBUFFERED=1
 ENV VIRTUAL_ENV=/app/.venv
@@ -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: 0.29.1
-appVersion: "0.29.1"
+version: 0.33.1
+appVersion: "0.33.1"
 keywords:
  - nextcloud
  - mcp
@@ -21,6 +21,10 @@ home: https://github.com/cbcoutinho/nextcloud-mcp-server
 sources:
  - https://github.com/cbcoutinho/nextcloud-mcp-server
 icon: https://raw.githubusercontent.com/nextcloud/server/master/core/img/logo/logo.svg
+annotations:
+  # Grafana dashboard support
+  grafana_dashboard: "true"
+  grafana_dashboard_folder: "Nextcloud MCP"
 dependencies:
  - name: qdrant
    version: "1.15.5"
@@ -280,6 +280,72 @@ Use OpenAI or any OpenAI-compatible API instead of Ollama.
 | `openai.secretKey` | Key in secret containing API key | `api-key` |
 | `openai.baseUrl` | Custom API endpoint (optional) | `""` |

+#### Observability & Monitoring
+
+The chart includes comprehensive observability features including Prometheus metrics, OpenTelemetry tracing, and Grafana dashboards.
+
+**Metrics Configuration:**
+
+| Parameter | Description | Default |
+|-----------|-------------|---------|
+| `observability.metrics.enabled` | Enable Prometheus metrics | `true` |
+| `observability.metrics.port` | Metrics port | `9090` |
+| `observability.metrics.path` | Metrics endpoint path | `/metrics` |
+
+**Tracing Configuration:**
+
+| Parameter | Description | Default |
+|-----------|-------------|---------|
+| `observability.tracing.enabled` | Enable OpenTelemetry tracing | `false` |
+| `observability.tracing.endpoint` | OTLP collector endpoint | `""` |
+| `observability.tracing.serviceName` | Service name in traces | `nextcloud-mcp-server` |
+| `observability.tracing.samplingRate` | Trace sampling rate (0.0-1.0) | `1.0` |
+
+**Logging Configuration:**
+
+| Parameter | Description | Default |
+|-----------|-------------|---------|
+| `observability.logging.format` | Log format (json or text) | `json` |
+| `observability.logging.level` | Log level | `INFO` |
+| `observability.logging.includeTraceContext` | Include trace IDs in logs | `true` |
+
+**ServiceMonitor (Prometheus Operator):**
+
+| Parameter | Description | Default |
+|-----------|-------------|---------|
+| `serviceMonitor.enabled` | Create ServiceMonitor resource | `false` |
+| `serviceMonitor.interval` | Scrape interval | `30s` |
+| `serviceMonitor.scrapeTimeout` | Scrape timeout | `10s` |
+| `serviceMonitor.labels` | Additional labels for ServiceMonitor | `{}` |
+
+**PrometheusRule (Prometheus Operator):**
+
+| Parameter | Description | Default |
+|-----------|-------------|---------|
+| `prometheusRule.enabled` | Create PrometheusRule with alert rules | `false` |
+| `prometheusRule.labels` | Additional labels for PrometheusRule | `{}` |
+
+**Grafana Dashboards:**
+
+| Parameter | Description | Default |
+|-----------|-------------|---------|
+| `dashboards.enabled` | Enable automatic dashboard provisioning | `false` |
+| `dashboards.grafanaFolder` | Grafana folder name for dashboards | `Nextcloud MCP` |
+| `dashboards.labels` | Additional labels for dashboard ConfigMap | `{}` |
+| `dashboards.annotations` | Additional annotations for dashboard ConfigMap | `{}` |
+
+When `dashboards.enabled` is `true`, a ConfigMap with the Grafana dashboard is created with the `grafana_dashboard: "1"` label. This enables automatic discovery by Grafana sidecar containers (commonly used with kube-prometheus-stack).
+
+The dashboard provides comprehensive monitoring including:
+- HTTP request metrics (RED pattern: Rate, Errors, Duration)
+- MCP tool performance and errors
+- Nextcloud API performance by app (notes, calendar, contacts, etc.)
+- OAuth token operations and cache hit rates
+- External dependency health (Nextcloud, Qdrant, Keycloak, Unstructured API)
+- Vector sync processing pipeline (when enabled)
+
+For manual import or more details, see `charts/nextcloud-mcp-server/dashboards/README.md`.
+
 ## Examples

 ### Example 1: Basic Auth with Ingress
@@ -6,14 +6,57 @@ This directory contains example Grafana dashboards for monitoring the Nextcloud

 ### nextcloud-mcp-server.json

-Comprehensive dashboard with the following panels:
+All-in-one Operations Dashboard with comprehensive monitoring across all system components.

- **Request Rate**: HTTP requests per second by method and endpoint
- **Error Rate**: Percentage of 5xx errors
- **Request Latency**: P50 and P95 latency by endpoint
- **Top MCP Tools**: Most frequently called tools
- **Nextcloud API Latency**: API call latency by app (notes, calendar, etc.)
- **Vector Sync Queue**: Queue size for background document processing
+#### Overview Row
+High-level metrics for quick health assessment:
+- **Request Rate** (stat): Total requests per second
+- **Error Rate** (stat): Percentage of 5xx errors with color thresholds
+- **P95 Latency** (stat): 95th percentile request latency
+- **Active Requests** (stat): Current in-flight requests
+
+#### HTTP Metrics (RED Pattern)
+Core request/error/duration metrics:
+- **Request Rate by Endpoint** (timeseries): RPS breakdown by endpoint
+- **Error Rate by Status Code** (timeseries): Error rates for 4xx/5xx codes
+- **Latency Percentiles** (timeseries): P50, P95, P99 latency trends
+- **Status Code Distribution** (piechart): Percentage breakdown of all status codes
+
+#### MCP Tools Row
+MCP-specific tool performance:
+- **Top Tools by Call Volume** (bargauge): Top 10 most-called tools
+- **Tool Error Rate** (timeseries): Error rates per tool
+- **Tool Execution Duration** (timeseries): P95 latency by tool
+
+#### Nextcloud API Row
+Backend API performance metrics:
+- **API Calls by App** (timeseries): Request rate per Nextcloud app (notes, calendar, contacts, etc.)
+- **API Latency by App** (timeseries): P95 latency per app
+- **API Retries by Reason** (timeseries): Retry patterns (429, timeout, connection errors)
+- **API Error Rate** (stat): Overall API error percentage
+
+#### OAuth & Authentication Row
+OAuth token operations and caching:
+- **Token Validations** (timeseries): Success/failure rates for token validation
+- **Token Exchange Operations** (timeseries): RFC 8693 token exchange operations
+- **Token Cache Hit Rate** (stat): Percentage of cache hits (color-coded: red<50%, yellow<80%, green≥80%)
+- **Refresh Token Operations** (timeseries): Refresh token storage operations by type
+
+#### Dependencies & Health Row
+External dependency status monitoring:
+- **Nextcloud Health** (stat): UP/DOWN status with color coding
+- **Qdrant Health** (stat): Vector database health status
+- **Keycloak Health** (stat): Identity provider health status
+- **Unstructured API Health** (stat): Document processing API status
+- **Health Check Duration** (timeseries): Health check latency by dependency
+- **Database Operation Latency** (timeseries): P95 latency for DB operations (SQLite, Qdrant)
+
+#### Vector Sync Row (when enabled)
+Document processing pipeline metrics:
+- **Documents Processed Rate** (timeseries): Processing throughput by status (success/failure)
+- **Processing Queue Depth** (gauge): Current queue size with thresholds (yellow>50, red>100)
+- **Qdrant Operations** (timeseries): Vector database operations by type
+- **Document Processing Duration** (timeseries): P95 processing latency

 ## Importing to Grafana

@@ -25,49 +68,77 @@ Comprehensive dashboard with the following panels:
 4. Select your Prometheus data source
 5. Click "Import"

-### Automated Import (Kubernetes)
+### Automated Import (Helm Chart)

-If using the Grafana Operator or kube-prometheus-stack, you can create a ConfigMap:
+The Helm chart now supports automatic dashboard provisioning via Grafana sidecar pattern.
+
+#### Option 1: Using Helm Chart (Recommended)
+
+Enable dashboard provisioning in your Helm values:
+
+```yaml
+# values.yaml for nextcloud-mcp-server chart
+dashboards:
+  enabled: true
+  grafanaFolder: "Nextcloud MCP"  # Folder name in Grafana
+  labels: {}  # Additional labels if needed
+```
+
+Then deploy or upgrade:

 ```bash
-kubectl create configmap nextcloud-mcp-dashboards \
+helm upgrade --install nextcloud-mcp nextcloud-mcp-server \
+  --set dashboards.enabled=true
+```
+
+The dashboard will be automatically imported by Grafana if the sidecar is configured
+to watch for ConfigMaps with label `grafana_dashboard: "1"`.
+
+#### Option 2: Using kube-prometheus-stack
+
+If using kube-prometheus-stack with Grafana sidecar enabled, the dashboard will be
+automatically discovered and imported. Ensure your Grafana deployment has:
+
+```yaml
+# kube-prometheus-stack values
+grafana:
+  sidecar:
+    dashboards:
+      enabled: true
+      label: grafana_dashboard
+      folder: /tmp/dashboards
+      provider:
+        foldersFromFilesStructure: true
+```
+
+#### Option 3: Manual ConfigMap Creation
+
+For other Grafana setups, create a ConfigMap manually:
+
+```bash
+kubectl create configmap nextcloud-mcp-dashboard \
  --from-file=nextcloud-mcp-server.json \
  -n monitoring

-# Add label for Grafana sidecar to discover
-kubectl label configmap nextcloud-mcp-dashboards \
+# Add sidecar discovery label
+kubectl label configmap nextcloud-mcp-dashboard \
  grafana_dashboard=1 \
  -n monitoring
-```

-Or add to your Helm values:
-
-```yaml
-# values.yaml for kube-prometheus-stack
-grafana:
-  dashboardProviders:
-    dashboardproviders.yaml:
-      apiVersion: 1
-      providers:
-        - name: 'nextcloud-mcp'
-          orgId: 1
-          folder: 'Nextcloud MCP'
-          type: file
-          disableDeletion: false
-          editable: true
-          options:
-            path: /var/lib/grafana/dashboards/nextcloud-mcp
-
-  dashboardsConfigMaps:
-    nextcloud-mcp: nextcloud-mcp-dashboards
+# Add folder annotation (annotations support spaces, unlike labels)
+kubectl annotate configmap nextcloud-mcp-dashboard \
+  grafana_folder="Nextcloud MCP" \
+  -n monitoring
 ```

 ## Dashboard Variables

-The dashboard includes two variables:
+The dashboard includes four template variables for dynamic filtering:

- **Data Source**: Select your Prometheus data source
- **Namespace**: Filter metrics by Kubernetes namespace
+- **datasource**: Select your Prometheus data source
+- **namespace**: Filter metrics by Kubernetes namespace (supports "All")
+- **pod**: Filter by specific pod(s) - multi-select enabled (supports "All")
+- **interval**: Query interval for rate calculations (1m, 5m, 10m, 30m, 1h - default: 5m)

 ## Customization

@@ -96,6 +96,30 @@ Your Nextcloud MCP Server has been deployed in {{ .Values.auth.mode }} authentic
   kubectl --namespace {{ .Release.Namespace }} exec -it deploy/{{ include "nextcloud-mcp-server.fullname" . }} -- curl -s http://localhost:{{ include "nextcloud-mcp-server.port" . }}/user/page | grep "Vector Sync"
 {{- end }}

+{{- if .Values.dashboards.enabled }}
+
+6. Grafana Dashboards:
+   - Dashboard provisioning: Enabled
+   - ConfigMap: {{ include "nextcloud-mcp-server.fullname" . }}-dashboard
+   - Grafana Folder: {{ .Values.dashboards.grafanaFolder }}
+
+   The dashboard will be automatically imported by Grafana if the sidecar is configured
+   to watch for ConfigMaps with label "grafana_dashboard: 1".
+
+   To manually import the dashboard:
+   kubectl --namespace {{ .Release.Namespace }} get configmap {{ include "nextcloud-mcp-server.fullname" . }}-dashboard -o jsonpath='{.data.nextcloud-mcp-server\.json}' | jq . > dashboard.json
+
+   Then import dashboard.json via Grafana UI (Dashboards → Import).
+{{- else }}
+
+6. Grafana Dashboards:
+   - Dashboard provisioning: Disabled
+   - To enable automatic dashboard provisioning, set: dashboards.enabled=true
+
+   Manual import option:
+   The dashboard JSON is available in the chart at charts/nextcloud-mcp-server/dashboards/nextcloud-mcp-server.json
+{{- end }}
+
 For more information and documentation:
 - GitHub: https://github.com/cbcoutinho/nextcloud-mcp-server
 - Documentation: https://github.com/cbcoutinho/nextcloud-mcp-server#readme
@@ -0,0 +1,25 @@
+{{- if .Values.dashboards.enabled }}
+apiVersion: v1
+kind: ConfigMap
+metadata:
+  name: {{ include "nextcloud-mcp-server.fullname" . }}-dashboard
+  namespace: {{ .Release.Namespace }}
+  labels:
+    {{- include "nextcloud-mcp-server.labels" . | nindent 4 }}
+    {{- with .Values.dashboards.labels }}
+    {{- toYaml . | nindent 4 }}
+    {{- end }}
+    # Grafana sidecar discovery label
+    grafana_dashboard: "1"
+  annotations:
+    {{- with .Values.dashboards.annotations }}
+    {{- toYaml . | nindent 4 }}
+    {{- end }}
+    # Grafana folder name (annotations support spaces, unlike labels)
+    {{- if .Values.dashboards.grafanaFolder }}
+    grafana_folder: {{ .Values.dashboards.grafanaFolder | quote }}
+    {{- end }}
+data:
+  nextcloud-mcp-server.json: |-
+{{ .Files.Get "dashboards/nextcloud-mcp-server.json" | indent 4 }}
+{{- end }}
@@ -218,8 +218,6 @@ spec:
            - name: METRICS_PORT
              value: {{ .Values.observability.metrics.port | quote }}
            {{- if .Values.observability.tracing.enabled }}
-            - name: OTEL_ENABLED
-              value: "true"
            - name: OTEL_EXPORTER_OTLP_ENDPOINT
              value: {{ .Values.observability.tracing.endpoint | quote }}
            - name: OTEL_SERVICE_NAME
@@ -205,6 +205,20 @@ prometheusRule:
  # Additional labels for PrometheusRule (e.g., for Prometheus selector)
  # Example: { prometheus: kube-prometheus }

+# Grafana dashboards (requires Grafana with sidecar enabled)
+dashboards:
+  # Enable automatic dashboard provisioning via ConfigMap
+  enabled: false
+  # Grafana folder name where dashboards will be imported
+  # The grafana-sidecar looks for ConfigMaps with label "grafana_dashboard: 1"
+  # and reads the folder name from annotation "grafana_folder" (supports spaces)
+  grafanaFolder: "Nextcloud MCP"
+  # Additional labels for dashboard ConfigMap
+  # These will be added alongside the required "grafana_dashboard: 1" label
+  labels: {}
+  # Additional annotations for dashboard ConfigMap
+  annotations: {}
+
 service:
  type: ClusterIP
  port: 8000
@@ -3,7 +3,7 @@ services:
  # https://hub.docker.com/_/mariadb
  db:
    # Note: Check the recommend version here: https://docs.nextcloud.com/server/latest/admin_manual/installation/system_requirements.html#server
-    image: docker.io/library/mariadb:lts@sha256:ae6119716edac6998ae85508431b3d2e666530ddf4e94c61a10710caec9b0f71
+    image: docker.io/library/mariadb:lts@sha256:404ebf26ed7a56fbab05c29f6f1e70188e5eadb51bba8cee8d355775776deb08
    restart: always
    command: --transaction-isolation=READ-COMMITTED
    volumes:
@@ -88,26 +88,30 @@ services:
      - VECTOR_SYNC_SCAN_INTERVAL=10
      - VECTOR_SYNC_PROCESSOR_WORKERS=1

-      - LOG_FORMAT=text
+      #- LOG_FORMAT=json

      # Qdrant configuration (three modes):
      # 1. Network mode: Set QDRANT_URL=http://qdrant:6333 (requires qdrant service)
      # 2. In-memory mode: Set QDRANT_LOCATION=:memory: (default if nothing set)
      # 3. Persistent local: Set QDRANT_LOCATION=/app/data/qdrant (stored in mcp-data volume)
-      - QDRANT_LOCATION=":memory:"  # In-memory mode for CI/testing (no external service required)
+      #- QDRANT_LOCATION=/app/data/qdrant  # In-memory mode used if not set
      #- QDRANT_URL=http://qdrant:6333  # Uncomment for network mode
      #- QDRANT_API_KEY=${QDRANT_API_KEY:-my_secret_api_key}  # Only for network mode

+      # Observability
+      #- OTEL_SERVICE_NAME=nextcloud-mcp-docker-compose
+      #- OTEL_EXPORTER_OTLP_ENDPOINT=http://otel-collector:4317
+
      # Collection naming: Auto-generated as {deployment-id}-{model-name}
      # - Deployment ID: OTEL_SERVICE_NAME (if set) or hostname (fallback)
      # - Model name: OLLAMA_EMBEDDING_MODEL
      # - Example: "nextcloud-mcp-server-nomic-embed-text"
      # - Changing models creates new collection (requires re-embedding)
      # - Set QDRANT_COLLECTION to override auto-generation:
-      - QDRANT_COLLECTION=nextcloud_content
+      #- QDRANT_COLLECTION=nextcloud_content

      # Ollama configuration (optional - uses SimpleEmbeddingProvider if not set)
-      # - OLLAMA_BASE_URL=https://ollama.internal.coutinho.io:443
+      # - OLLAMA_BASE_URL=http://ollama:11434
      # - OLLAMA_EMBEDDING_MODEL=nomic-embed-text  # Changing this creates new collection
      # - OLLAMA_VERIFY_SSL=false

@@ -219,7 +223,7 @@ services:
      - keycloak-oauth-storage:/app/.oauth

  qdrant:
-    image: qdrant/qdrant:v1.15.5
+    image: qdrant/qdrant:v1.15.5@sha256:0fb8897412abc81d1c0430a899b9a81eb8328aa634e7242d1bc804c1fe8fe863
    restart: always
    ports:
      - 127.0.0.1:6333:6333  # REST API
@@ -377,7 +377,7 @@ async def get_vector_sync_status(ctx: Context) -> dict:
    }
 ```

-The web UI (`/user/page` route) mirrors these controls with a simple toggle switch for enabling/disabling sync and a status display showing indexed counts and sync state. There is no job history, no detailed progress bars, no per-document status—just the essential information users need.
+The web UI (`/app` route) mirrors these controls with a simple toggle switch for enabling/disabling sync and a status display showing indexed counts and sync state. There is no job history, no detailed progress bars, no per-document status—just the essential information users need.

 ### Authentication and Offline Access

@@ -0,0 +1,661 @@
+# ADR-010: Webhook-Based Vector Database Synchronization
+
+**Status**: Proposed
+**Date**: 2025-01-10
+**Depends On**: ADR-007 (Background Vector Sync)
+
+## Context
+
+ADR-007 established a background synchronization architecture for maintaining the vector database using periodic polling. The scanner task runs on a configurable interval (default 3600 seconds / 1 hour) to detect changed documents across Nextcloud apps. While this polling approach is simple and reliable, it introduces significant latency between content changes and vector database updates.
+
+### Current Polling Architecture
+
+The existing scanner implementation in `nextcloud_mcp_server/vector/scanner.py` operates as follows:
+
+1. **Periodic Scanning**: The scanner task sleeps for `vector_sync_scan_interval` seconds between runs
+2. **Change Detection**: For each scan, it:
+   - Fetches all documents from Nextcloud (notes, calendar events, etc.)
+   - Queries Qdrant for the last indexed timestamp of each document
+   - Compares modification timestamps to detect changes
+   - Queues changed documents for processing
+3. **Document Processing**: Processor tasks pull from the queue, generate embeddings, and update Qdrant
+
+This architecture works but has fundamental limitations:
+
+**Latency**: With a 1-hour scan interval, content changes can take up to 1 hour to appear in semantic search results. For time-sensitive use cases (e.g., "What's on my calendar today?"), this delay is problematic.
+
+**API Load**: Every scan fetches *all* documents for *all* enabled users, regardless of whether anything changed. For large deployments with thousands of documents, this generates significant unnecessary API traffic to Nextcloud.
+
+**Resource Waste**: The scanner and processors consume compute resources even when no content has changed. During periods of low activity, the system performs wasteful polling.
+
+**Scalability**: As the number of users and documents grows, the time required to complete a full scan increases. Eventually, the scan duration may exceed the scan interval, causing scans to run continuously without idle periods.
+
+**Rate Limiting**: Fetching all documents for all users in rapid succession can trigger Nextcloud's rate limiting, especially on shared hosting environments with restrictive API quotas.
+
+These limitations are inherent to any polling-based architecture. Reducing the scan interval (e.g., to 5 minutes) reduces latency but exacerbates API load, resource waste, and rate limiting issues. The fundamental problem is that the system has no way to know *when* content changes occur—it must repeatedly check to find out.
+
+### Nextcloud Webhook Listeners
+
+Nextcloud provides a webhook_listeners app (bundled with Nextcloud 30+) that enables push-based change notifications. Instead of polling for changes, external services can register webhook endpoints and receive HTTP POST requests when specific events occur. Administrators register these webhooks using Nextcloud's OCS API or occ commands.
+
+The webhook_listeners app supports events for all Nextcloud apps relevant to this MCP server's vector database:
+
+**Files/Notes Events** (notes are stored as files):
+- `OCP\Files\Events\Node\NodeCreatedEvent`
+- `OCP\Files\Events\Node\NodeWrittenEvent`
+- `OCP\Files\Events\Node\BeforeNodeDeletedEvent` ⭐ **Use this for deletion (includes node.id)**
+- `OCP\Files\Events\Node\NodeDeletedEvent` (missing node.id - file already deleted)
+- `OCP\Files\Events\Node\NodeRenamedEvent`
+- `OCP\Files\Events\Node\NodeCopiedEvent`
+
+**Calendar Events**:
+- `OCP\Calendar\Events\CalendarObjectCreatedEvent`
+- `OCP\Calendar\Events\CalendarObjectUpdatedEvent`
+- `OCP\Calendar\Events\CalendarObjectDeletedEvent`
+- `OCP\Calendar\Events\CalendarObjectMovedEvent`
+
+**Tables Events**:
+- `OCA\Tables\Event\RowAddedEvent`
+- `OCA\Tables\Event\RowUpdatedEvent`
+- `OCA\Tables\Event\RowDeletedEvent`
+
+**Deck Events** (via file events since cards are stored as files in some configurations)
+
+Each webhook notification includes rich metadata:
+- User ID who triggered the event
+- Timestamp of the event
+- Document ID and metadata
+- Operation type (create, update, delete)
+- Path information (for files)
+
+Webhook notifications are dispatched via background jobs, with configurable delivery guarantees. Administrators can set up dedicated webhook worker processes to achieve near-real-time delivery (within seconds of the triggering event).
+
+### Why Not Replace Polling Entirely?
+
+While webhooks provide superior latency and efficiency, they cannot fully replace polling:
+
+**Missed Events**: If the MCP server is down when a webhook fires, the notification is lost. Nextcloud's background job system processes webhooks asynchronously, but does not queue failed deliveries indefinitely.
+
+**Administrator Setup**: Webhooks must be registered by Nextcloud administrators using the OCS API or occ commands. This is an optional optimization that administrators can enable when they want to reduce polling frequency.
+
+**Filter Configuration**: Webhook filters must be carefully configured to avoid notification floods. A poorly configured filter could send thousands of notifications for bulk operations (e.g., importing a calendar with hundreds of events).
+
+**Graceful Degradation**: In environments where webhooks are not configured, the system continues using polling without any degradation in functionality.
+
+**Deletion Detection**: Nextcloud's webhook system does not guarantee delivery of deletion events if the user's account is removed or the app is uninstalled. Periodic polling provides a safety mechanism to detect orphaned documents.
+
+A complementary architecture where webhooks supplement (but don't replace) polling provides low-latency updates when configured, with polling ensuring reliability.
+
+### Design Considerations
+
+**Push vs Pull Trade-offs**:
+Webhooks introduce new failure modes (network issues, endpoint unavailability, notification floods) that polling avoids. The webhook endpoint must handle failures gracefully without blocking semantic search functionality.
+
+**Webhook Endpoint Security**:
+The MCP server exposes an HTTP endpoint to receive webhooks. Authentication is optional—in production deployments, administrators can configure Nextcloud to send an `Authorization` header that the MCP server validates. For local development, authentication can be disabled for simplicity.
+
+**Idempotency**:
+The system may receive duplicate notifications (webhook + next scan) or out-of-order notifications (update fires before create completes). Document processing must be idempotent—processing the same document multiple times produces the same result.
+
+**Asynchronous Processing**:
+Nextcloud processes webhooks via background jobs, introducing delivery latency (typically seconds to minutes depending on background job configuration). This affects testing strategies—integration tests cannot rely on immediate webhook delivery.
+
+**Deployment Patterns**:
+The MCP server webhook endpoint is accessible at the same host/port as the MCP server itself. Administrators configure Nextcloud to POST to `https://<mcp-server-host>:<port>/webhooks/nextcloud` when registering webhook listeners.
+
+## Decision
+
+We will add a webhook endpoint to the MCP server that receives change notifications from Nextcloud and queues documents for vector database processing. This complements the existing polling architecture from ADR-007 without replacing it—webhooks provide low-latency updates when configured, while polling ensures reliability regardless of webhook availability.
+
+The architecture is intentionally simple: the webhook endpoint is just another producer of `DocumentTask` objects that feed into the existing processor queue. The scanner task, processor pool, and queue management remain unchanged from ADR-007.
+
+### Architecture Components
+
+**1. Webhook Endpoint**
+
+A new Starlette HTTP route will be added to receive webhook notifications from Nextcloud:
+
+```python
+from starlette.requests import Request
+from starlette.responses import JSONResponse
+
+@app.route("/webhooks/nextcloud", methods=["POST"])
+async def handle_nextcloud_webhook(request: Request) -> JSONResponse:
+    """
+    Receive webhook notifications from Nextcloud.
+
+    Parses event payload, extracts document metadata, and queues
+    changed documents for processing using the same queue as the scanner.
+    """
+    # 1. Optional authentication validation
+    if settings.webhook_secret:
+        auth_header = request.headers.get("authorization", "")
+        if not auth_header.startswith("Bearer ") or \
+           auth_header[7:] != settings.webhook_secret:
+            logger.warning("Webhook authentication failed")
+            return JSONResponse(
+                {"status": "error", "message": "Unauthorized"},
+                status_code=401
+            )
+
+    # 2. Parse webhook payload
+    payload = await request.json()
+    event_class = payload["event"]["class"]
+    user_id = payload["user"]["uid"]
+
+    # 3. Extract document metadata from event
+    doc_task = extract_document_task(event_class, payload)
+    if not doc_task:
+        return JSONResponse({"status": "ignored", "reason": "unsupported event"})
+
+    # 4. Send to processor queue (same queue as scanner)
+    try:
+        await webhook_send_stream.send(doc_task)
+        logger.info(f"Queued document from webhook: {doc_task}")
+        return JSONResponse({"status": "queued"})
+    except Exception as e:
+        logger.error(f"Failed to queue webhook document: {e}")
+        return JSONResponse(
+            {"status": "error", "message": str(e)},
+            status_code=500
+        )
+```
+
+The endpoint:
+- Validates optional authentication via `Authorization: Bearer <secret>` header
+- Parses various event types (calendar, files, tables) into `DocumentTask` objects
+- Sends to the same processing queue that the scanner uses
+- Returns quickly (<50ms) to avoid blocking Nextcloud's webhook workers
+- Handles errors gracefully (invalid payload, queue full, etc.)
+
+**2. Webhook Registration Helper (Development Only)**
+
+For development and testing purposes, a helper method will be added to `NextcloudClient` for registering webhooks via the OCS API. This is NOT exposed as an MCP tool—administrators register webhooks manually using Nextcloud's admin interface or the OCS API directly.
+
+```python
+class NextcloudClient:
+    async def register_webhook(
+        self,
+        event_type: str,
+        uri: str,
+        http_method: str = "POST",
+        auth_method: str = "none",
+        headers: dict[str, str] | None = None,
+    ) -> dict:
+        """
+        Register a webhook with Nextcloud (requires admin credentials).
+
+        Used for development/testing. Production admins should register
+        webhooks using Nextcloud's admin UI or occ commands.
+        """
+        # Implementation uses OCS API: POST /ocs/v2.php/apps/webhook_listeners/api/v1/webhooks
+        ...
+```
+
+This keeps webhook registration out of the MCP tool surface while providing a convenient API for integration tests.
+
+**3. Event Parsing**
+
+A helper function extracts `DocumentTask` from various Nextcloud event types:
+
+```python
+def extract_document_task(event_class: str, payload: dict) -> DocumentTask | None:
+    """Extract DocumentTask from webhook event payload."""
+    user_id = payload["user"]["uid"]
+    event_data = payload["event"]
+
+    # File/Note events
+    if "NodeCreatedEvent" in event_class or "NodeWrittenEvent" in event_class:
+        # Only process markdown files (notes)
+        path = event_data["node"]["path"]
+        if not path.endswith(".md"):
+            return None
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=event_data["node"]["id"],
+            doc_type="note",
+            operation="index",
+            modified_at=payload["time"],
+        )
+
+    # Calendar events
+    elif "CalendarObjectCreatedEvent" in event_class or \
+         "CalendarObjectUpdatedEvent" in event_class:
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=str(event_data["objectData"]["id"]),
+            doc_type="calendar_event",
+            operation="index",
+            modified_at=event_data["objectData"]["lastmodified"],
+        )
+
+    # Deletion events (use BeforeNodeDeletedEvent for files to get node.id)
+    elif "BeforeNodeDeletedEvent" in event_class or \
+         "NodeDeletedEvent" in event_class or \
+         "CalendarObjectDeletedEvent" in event_class:
+        # Similar logic for delete operations
+        ...
+
+    return None  # Unsupported event type
+```
+
+**4. No Changes to Scanner or Processors**
+
+The existing scanner task from ADR-007 continues operating unchanged. It polls Nextcloud on its configured interval (`VECTOR_SYNC_SCAN_INTERVAL`), discovers changed documents, and queues them for processing. The scanner is unaware of webhooks—it simply adds `DocumentTask` objects to the queue.
+
+Similarly, the processor pool continues pulling `DocumentTask` objects from the queue, generating embeddings, and updating Qdrant. Processors don't know or care whether a task came from the scanner or a webhook.
+
+This design keeps concerns separated: webhooks and scanner are independent producers, processors are independent consumers, and the queue mediates between them.
+
+### Configuration
+
+A new optional environment variable controls webhook authentication:
+
+```bash
+# Optional: Shared secret for webhook authentication
+# If set, webhooks must include "Authorization: Bearer <secret>" header
+# If unset, no authentication is required (useful for local development)
+WEBHOOK_SECRET=<generate-random-secret>
+```
+
+The webhook endpoint is automatically available at `/webhooks/nextcloud` when the MCP server starts. No feature flags or additional configuration needed—if Nextcloud sends webhooks to this endpoint, they will be processed.
+
+**Reducing Polling Frequency**: Administrators who configure webhooks may want to reduce polling frequency to minimize API load while maintaining safety reconciliation scans:
+
+```bash
+# Increase scan interval from 1 hour (default) to 24 hours
+VECTOR_SYNC_SCAN_INTERVAL=86400
+```
+
+This is a manual configuration decision, not automatic—the scanner doesn't adapt based on webhook availability.
+
+### Webhook Event Mapping
+
+The webhook handler maps Nextcloud events to document types:
+
+| Nextcloud Event | Document Type | Operation |
+|----------------|---------------|-----------|
+| `NodeCreatedEvent` (path: `*/files/*.md`) | `note` | `index` |
+| `NodeWrittenEvent` (path: `*/files/*.md`) | `note` | `index` |
+| `NodeDeletedEvent` (path: `*/files/*.md`) | `note` | `delete` |
+| `CalendarObjectCreatedEvent` | `calendar_event` | `index` |
+| `CalendarObjectUpdatedEvent` | `calendar_event` | `index` |
+| `CalendarObjectDeletedEvent` | `calendar_event` | `delete` |
+| `RowAddedEvent` | `table_row` | `index` |
+| `RowUpdatedEvent` | `table_row` | `index` |
+| `RowDeletedEvent` | `table_row` | `delete` |
+
+Path filters in webhook registration ensure only relevant files trigger notifications (e.g., exclude `.jpg`, `.mp4` for file events).
+
+### Administrator Setup
+
+Administrators who want to enable webhooks:
+
+1. **Enable webhook_listeners app** in Nextcloud: `occ app:enable webhook_listeners`
+2. **Register webhook endpoints** using Nextcloud's OCS API or admin UI:
+   - Endpoint: `https://<mcp-server-host>:<port>/webhooks/nextcloud`
+   - Events: File created/updated/deleted, Calendar object events, Table row events
+   - Filters: Exclude non-content files (images, videos), system directories
+   - Optional: Configure `Authorization: Bearer <WEBHOOK_SECRET>` header
+3. **Optionally reduce scanner frequency**: Set `VECTOR_SYNC_SCAN_INTERVAL=86400` (24 hours)
+4. **Set up webhook workers** (optional): Configure dedicated background job workers for low-latency delivery
+
+Existing deployments continue using polling without any changes. Webhooks are purely additive.
+
+## Consequences
+
+### Benefits
+
+**Reduced Latency**: With webhooks configured, content changes appear in semantic search within seconds to minutes (depending on Nextcloud background job configuration) instead of up to 1 hour. Queries like "What meetings do I have today?" reflect recent calendar updates.
+
+**Lower API Load**: Administrators who configure webhooks can reduce scanner frequency (e.g., 24-hour intervals), eliminating most polling API calls while maintaining safety reconciliation scans. This significantly reduces load on Nextcloud servers.
+
+**Better Scalability**: Webhooks scale better than polling as content volume grows. The system only processes changed documents instead of checking all documents every hour.
+
+**Simple Architecture**: The webhook endpoint is just another producer feeding the existing processor queue. No changes to scanner, processors, or queue management—webhooks integrate cleanly into the existing architecture.
+
+**Improved User Experience**: Lower-latency semantic search feels more responsive and accurate, especially for time-sensitive queries about recent changes.
+
+### Drawbacks
+
+**Manual Configuration**: Administrators must configure webhooks outside the MCP server using Nextcloud's admin tools. This adds setup complexity compared to the zero-configuration polling approach.
+
+**Deployment Requirements**: Webhooks require the MCP server to be reachable from Nextcloud via HTTP(S). Deployments behind NAT or with restrictive firewalls may not support webhooks without additional networking configuration.
+
+**Asynchronous Delivery**: Nextcloud processes webhooks via background jobs, introducing delivery latency (typically seconds to minutes). The exact latency depends on background job worker configuration and system load.
+
+**Testing Complexity**: Integration tests cannot rely on immediate webhook delivery due to asynchronous background job processing. Tests must either poll for results or mock webhook delivery directly.
+
+**New Failure Modes**: Webhook endpoint downtime, network issues between Nextcloud and MCP server, webhook notification floods from bulk operations. The system must handle these gracefully.
+
+**Version Dependencies**: The webhook_listeners app requires Nextcloud 30+. Older versions continue using polling exclusively.
+
+### Monitoring and Observability
+
+New metrics track webhook performance:
+
+- `webhook_notifications_received_total{event_type}`: Count of webhook notifications by event type
+- `webhook_processing_duration_seconds{event_type}`: Webhook handler latency
+- `webhook_errors_total{error_type}`: Failed webhook processing by error type (auth failure, parse error, queue full)
+
+Logs include:
+- Successful webhook processing: `Queued document from webhook: DocumentTask(...)`
+- Webhook authentication failures: `Webhook authentication failed`
+- Parse errors: `Failed to parse webhook payload: ...`
+- Unsupported events: `Ignoring webhook for unsupported event: ...`
+
+### Security Considerations
+
+**Optional Authentication**: When `WEBHOOK_SECRET` is configured, webhook requests must include `Authorization: Bearer <WEBHOOK_SECRET>` header. The server validates this before processing to prevent unauthorized document queueing. For local development, authentication can be disabled by leaving `WEBHOOK_SECRET` unset.
+
+**Payload Validation**: Webhook payloads are parsed and validated against expected schemas. Malformed payloads are rejected with 400 Bad Request responses.
+
+**No Scope Enforcement**: Unlike MCP tools, webhooks do not enforce progressive consent or check if users have enabled semantic search. Webhooks queue all document changes—administrators control which events trigger webhooks via Nextcloud filters. This keeps the webhook endpoint simple and stateless.
+
+### Testing Strategy
+
+**Unit Tests**: Test webhook handler logic, event parsing, and authentication validation using mocked payloads:
+
+```python
+async def test_webhook_endpoint_parses_note_created_event():
+    """Unit test: webhook endpoint extracts DocumentTask from note created event."""
+    payload = {
+        "user": {"uid": "alice"},
+        "time": 1704067200,
+        "event": {
+            "class": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+            "node": {"id": "123", "path": "/alice/files/test.md"}
+        }
+    }
+    # Mock send_stream and verify DocumentTask is queued
+    ...
+```
+
+**Integration Tests (Without Real Webhooks)**: Since Nextcloud processes webhooks asynchronously via background jobs, integration tests should NOT rely on triggering real Nextcloud events and waiting for webhook delivery. Instead, tests should:
+
+1. **Mock webhook delivery**: POST webhook payloads directly to the `/webhooks/nextcloud` endpoint
+2. **Verify processing**: Check that documents are queued and eventually appear in Qdrant
+3. **Test authentication**: Verify requests without valid auth header are rejected (when `WEBHOOK_SECRET` is set)
+
+```python
+async def test_webhook_integration_mocked_delivery():
+    """Integration test: webhook handler queues document for processing."""
+    # POST webhook payload directly to endpoint (bypass Nextcloud)
+    response = await client.post("/webhooks/nextcloud", json=note_created_payload)
+    assert response.status_code == 200
+
+    # Wait for processor to handle document
+    await asyncio.sleep(2)
+
+    # Verify document appears in Qdrant
+    results = await qdrant_client.scroll(...)
+    assert len(results[0]) > 0
+```
+
+**Manual Testing (Real Webhooks)**: For end-to-end validation with real Nextcloud webhook delivery:
+
+1. Register webhook via OCS API or `NextcloudClient.register_webhook()` helper
+2. Configure webhook background job workers for low-latency delivery
+3. Trigger Nextcloud events (create note, add calendar event)
+4. Monitor MCP server logs for webhook delivery
+5. Verify documents appear in Qdrant after background job processing
+
+**Failure Mode Tests**:
+- Invalid authentication: Verify 401 response when auth header is missing/incorrect
+- Malformed payload: Verify 400 response for invalid JSON or missing required fields
+- Unsupported event types: Verify graceful handling (ignored, not error)
+- Queue full: Verify 500 response with appropriate error message
+
+### Future Enhancements
+
+**Batch Processing**: Group multiple webhook notifications within a short time window (e.g., 5 seconds) into a single batch before queueing. This reduces processor overhead during bulk operations like importing calendars.
+
+**Webhook Payload Optimization**: For large documents, Nextcloud could be configured to send minimal metadata in webhooks (just user_id, doc_id, doc_type), with processors fetching full content lazily. This reduces webhook payload size and network bandwidth.
+
+**Deduplication Window**: Track recently processed documents (last 5 minutes) to avoid redundant work when webhooks and scanner both detect the same change. The processor can check a simple in-memory cache before fetching document content.
+
+## Appendix A: Manual Webhook Testing Results (2025-01-11)
+
+### Testing Summary
+
+Manual validation of Nextcloud webhook schemas and behavior confirmed that webhooks work as documented with several important findings for implementation. **5 out of 6** webhook types were successfully captured and validated.
+
+**Test Environment:**
+- Nextcloud 30+ (Docker compose)
+- webhook_listeners app enabled
+- Test endpoint: `http://mcp:8000/webhooks/nextcloud`
+- Background webhook worker running (60s timeout)
+
+**Results:**
+- ✅ NodeCreatedEvent (file creation)
+- ✅ NodeWrittenEvent (file update)
+- ✅ NodeDeletedEvent (file deletion)
+- ✅ CalendarObjectCreatedEvent
+- ✅ CalendarObjectUpdatedEvent
+- ❌ CalendarObjectDeletedEvent (webhook did not fire - potential Nextcloud bug)
+
+### Critical Implementation Findings
+
+#### 1. Deletion Events Lack `node.id` Field
+
+**Finding:** `NodeDeletedEvent` payloads do NOT include `event.node.id`, only `event.node.path`.
+
+**Example:**
+```json
+{
+  "user": {"uid": "admin", "displayName": "admin"},
+  "time": 1762851093,
+  "event": {
+    "class": "OCP\\Files\\Events\\Node\\NodeDeletedEvent",
+    "node": {
+      "path": "/admin/files/Notes/Webhooks/Webhook Test Note.md"
+      // NOTE: No "id" field present
+    }
+  }
+}
+```
+
+**Impact:** The event parser in this ADR's example code assumes `event_data["node"]["id"]` exists for all file events. This will fail for deletions.
+
+**Update (2025-11-11):** Nextcloud maintainer clarified that `BeforeNodeDeletedEvent` should be used instead of `NodeDeletedEvent` to access `node.id` before the file is deleted. See [issue #56371](https://github.com/nextcloud/server/issues/56371#issuecomment-2470896634).
+
+> "Try using the `BeforeNodeDeletedEvent`. The `id` should still be available at that time. The reason `id` is not in `NodeDeletedEvent` is because the file is effectively guaranteed to be gone and, in turn, so is the FileInfo."
+> — Josh Richards, Nextcloud maintainer
+
+**Recommended Solution:** Use `OCP\Files\Events\Node\BeforeNodeDeletedEvent` for file deletion webhooks instead of `NodeDeletedEvent`.
+
+**Alternative Fix (if using NodeDeletedEvent):** Check for `id` existence and fall back to path-based identification:
+
+```python
+def extract_document_task(event_class: str, payload: dict) -> DocumentTask | None:
+    user_id = payload["user"]["uid"]
+    event_data = payload["event"]
+
+    # File deletion events - NO node.id field
+    if "NodeDeletedEvent" in event_class:
+        path = event_data["node"]["path"]
+        if not path.endswith(".md"):
+            return None
+        # Use path-based ID since node.id is unavailable
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=f"path:{path}",  # Prefix to distinguish from numeric IDs
+            doc_type="note",
+            operation="delete",
+            modified_at=payload["time"],
+        )
+
+    # File creation/update events - node.id exists
+    elif "NodeCreatedEvent" in event_class or "NodeWrittenEvent" in event_class:
+        path = event_data["node"]["path"]
+        if not path.endswith(".md"):
+            return None
+
+        # Check if 'id' exists (should, but be defensive)
+        node_id = event_data["node"].get("id")
+        if not node_id:
+            # Fallback for missing ID
+            node_id = f"path:{path}"
+
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=str(node_id),
+            doc_type="note",
+            operation="index",
+            modified_at=payload["time"],
+        )
+```
+
+**Qdrant Deletion Strategy:** When deleting by path-based ID, search Qdrant for documents with matching path metadata:
+
+```python
+async def delete_document_by_path(user_id: str, path: str):
+    """Delete document from Qdrant using path (when ID unavailable)."""
+    points = await qdrant.scroll(
+        collection_name=collection,
+        scroll_filter=Filter(must=[
+            FieldCondition(key="user_id", match=MatchValue(value=user_id)),
+            FieldCondition(key="metadata.path", match=MatchValue(value=path)),
+        ]),
+    )
+    # Delete found points...
+```
+
+#### 2. Multiple Webhooks Per Operation
+
+**Finding:** Creating a single note triggers 3-5 separate webhook events in rapid succession:
+
+1. `NodeCreatedEvent` for parent folder (if new)
+2. `NodeWrittenEvent` for parent folder
+3. `NodeCreatedEvent` for the note file
+4. `NodeWrittenEvent` for the note file (sometimes fires twice)
+
+**Impact:** Without deduplication, the processor will fetch and index the same note multiple times within seconds, wasting compute and API quota.
+
+**Solution:** The processor queue should be idempotent. If the same document is queued multiple times, only the latest version needs processing. Implementation options:
+
+1. **Queue-level deduplication:** Before adding to queue, check if a task for the same `(user_id, doc_id)` is already pending. Replace the existing task instead of adding duplicate.
+
+2. **Processor-level deduplication:** Track recently processed documents in a short-lived cache (5 minutes). If a document was just processed, skip redundant fetch unless the `modified_at` timestamp is newer.
+
+3. **Accept duplicates:** Let the processor handle duplicates naturally. Qdrant upserts are idempotent—reindexing with identical content is harmless but wasteful.
+
+**Recommendation:** Implement queue-level deduplication by maintaining a map of pending tasks and replacing duplicates with newer timestamps.
+
+#### 3. Type Discrepancy in `node.id`
+
+**Finding:** Nextcloud documentation specifies `node.id` as type `string`, but actual payloads return `int`:
+
+```json
+"node": {
+  "id": 437,  // integer, not "437"
+  "path": "/admin/files/Notes/Webhooks/Webhook Test Note.md"
+}
+```
+
+**Impact:** Code that assumes `node.id` is always a string will work but may cause type confusion in strongly-typed languages.
+
+**Solution:** Explicitly convert to string when extracting: `doc_id=str(event_data["node"]["id"])`
+
+#### 4. Calendar Events Have Different ID Field Path
+
+**Finding:** Calendar events store the document ID in a different location than file events:
+
+- **File events:** `event.node.id`
+- **Calendar events:** `event.objectData.id`
+
+**Impact:** Event parser must handle different field paths for different event types. The example code in this ADR correctly shows this difference.
+
+**Calendar Event Deletion:** Calendar deletion webhooks did NOT fire during testing. This may be a Nextcloud bug or require specific configuration (e.g., trash bin enabled). Until resolved, calendar deletions will only be detected via periodic scanner runs.
+
+#### 5. Rich Metadata in Calendar Webhooks
+
+**Finding:** Calendar webhook payloads include extensive metadata not present in file webhooks:
+
+```json
+{
+  "event": {
+    "calendarId": 1,
+    "calendarData": {
+      "id": 1,
+      "uri": "personal",
+      "{http://calendarserver.org/ns/}getctag": "...",
+      "{http://sabredav.org/ns}sync-token": 21,
+      // ... many calendar-level properties
+    },
+    "objectData": {
+      "id": 3,
+      "uri": "webhook-test-event-001.ics",
+      "lastmodified": 1762851169,
+      "etag": "\"2b937b7d77dc83c77329dfdb210ba9d0\"",
+      "calendarid": 1,
+      "size": 297,
+      "component": "vevent",
+      "classification": 0,
+      "uid": "webhook-test-event-001@nextcloud",
+      "calendardata": "BEGIN:VCALENDAR\r\nVERSION:2.0\r\n...",  // Full iCal
+      "{http://nextcloud.com/ns}deleted-at": null
+    },
+    "shares": []  // Array of sharing info
+  }
+}
+```
+
+**Opportunity:** The full iCal content is available in `objectData.calendardata`. The processor could extract metadata directly from the webhook payload instead of making an additional CalDAV request, reducing API load.
+
+### Updated Event Mapping
+
+Based on testing, the actual webhook behavior:
+
+| Nextcloud Event | Fires? | `node.id`/`objectData.id` Present? | Notes |
+|----------------|--------|-------------------------------------|-------|
+| `NodeCreatedEvent` | ✅ Yes | ✅ Yes (`int`) | Fires for folders too |
+| `NodeWrittenEvent` | ✅ Yes | ✅ Yes (`int`) | Fires 1-2x per operation |
+| `NodeDeletedEvent` | ✅ Yes | ❌ **NO** (only `path`) | Critical difference |
+| `CalendarObjectCreatedEvent` | ✅ Yes | ✅ Yes (`objectData.id`) | Full iCal included |
+| `CalendarObjectUpdatedEvent` | ✅ Yes | ✅ Yes (`objectData.id`) | Full iCal included |
+| `CalendarObjectDeletedEvent` | ❌ **DID NOT FIRE** | ❓ Unknown | Possible Nextcloud bug |
+
+### Recommended Implementation Changes
+
+The webhook handler code in this ADR requires these modifications:
+
+1. **Handle missing `node.id` in deletions** (see code example in Finding #1)
+2. **Add deduplication logic** to prevent redundant processing from multiple webhooks per operation
+3. **Validate field existence** before accessing nested properties (`get()` with defaults)
+4. **Log unsupported events** at DEBUG level (not WARNING) to avoid log noise
+5. **Add calendar deletion fallback:** Since webhook unreliable, calendar deletions rely on scanner reconciliation
+6. **Consider payload optimization:** Extract calendar metadata from webhook payload to reduce CalDAV API calls
+
+### Testing Implications
+
+**Integration Test Strategy:**
+
+The asynchronous nature of Nextcloud webhooks makes real webhook delivery unreliable for automated tests:
+
+- ✅ **DO:** POST webhook payloads directly to `/webhooks/nextcloud` endpoint in tests
+- ❌ **DON'T:** Trigger Nextcloud events and wait for webhook delivery
+- ✅ **DO:** Test authentication, payload parsing, and queue integration with mocked payloads
+- ❌ **DON'T:** Assume webhooks fire immediately or reliably
+
+**Manual Testing Required:**
+- Real webhook delivery latency (depends on background job workers)
+- Calendar deletion webhook behavior (confirm bug or configuration issue)
+- Behavior under high-frequency updates (bulk operations)
+- Network failure handling (Nextcloud can't reach MCP server)
+
+### Complete Tested Payload Examples
+
+See `webhook-testing-findings.md` in the repository root for:
+- Complete JSON payloads for all tested events
+- Detailed schema validation results
+- Additional edge cases and observations
+- Screenshots of webhook logs
+
+## References
+
+- ADR-007: Background Vector Database Synchronization (polling architecture)
+- Nextcloud Documentation: `~/Software/documentation/admin_manual/webhook_listeners/index.rst`
+- Nextcloud OCS API: Webhook registration endpoint
+- Current scanner implementation: `nextcloud_mcp_server/vector/scanner.py:37`
+- Webhook Testing Report: `webhook-testing-findings.md` (2025-01-11)
@@ -0,0 +1,895 @@
+# ADR-011: Improving Semantic Search Quality Through Better Chunking and Embeddings
+
+**Status**: Proposed
+**Date**: 2025-11-12
+**Authors**: Development Team
+**Related**: ADR-003 (Vector Database Architecture), ADR-008 (MCP Sampling for RAG)
+
+## Context
+
+The semantic search implementation provides document retrieval across Nextcloud apps using vector embeddings. Production usage has revealed that **the system frequently misses relevant documents** (recall problem).
+
+Root cause analysis identifies two fundamental issues:
+
+### 1. Poor Chunking Strategy
+
+**Current Implementation** (`nextcloud_mcp_server/vector/document_chunker.py:36`):
+```python
+words = content.split()  # Naive whitespace splitting
+chunk_size = 512  # words
+overlap = 50  # words
+chunks = [words[i:i+chunk_size] for i in range(0, len(words), chunk_size-overlap)]
+```
+
+**Problems**:
+- **Breaks semantic boundaries**: Splits mid-sentence, mid-paragraph, mid-thought
+- **Loses context**: "The meeting discussed budget. We decided to..." becomes two disconnected chunks
+- **Poor retrieval**: Relevant content split across chunks with low individual relevance scores
+- **No structure awareness**: Ignores markdown headers, lists, code blocks
+
+**Evidence**:
+- Documents with relevant content in middle sections score poorly (content split across 3+ chunks)
+- Multi-sentence concepts (spanning 60-100 words) are fragmented
+- Search for "budget planning process" misses documents where these words appear in adjacent sentences but different chunks
+
+### 2. Suboptimal Embedding Model
+
+**Current Implementation** (`nextcloud_mcp_server/embedding/ollama_provider.py:33`):
+```python
+_model = "nomic-embed-text"  # 768 dimensions
+_dimension = 768  # Hardcoded
+```
+
+**Problems**:
+- **Model selection**: `nomic-embed-text` is general-purpose, not optimized for our use case
+- **No benchmarking**: Selected without comparative evaluation
+- **Dimensionality**: 768-dim may be insufficient for nuanced semantic distinctions
+- **No domain adaptation**: Model not tuned for Nextcloud content (notes, calendar, deck cards)
+
+**Evidence**:
+- Synonymous queries return different results ("meeting notes" vs. "discussion summary")
+- Domain-specific terms poorly represented ("standup", "retrospective", "OKRs")
+- Cross-lingual content (if present) not well supported
+
+### Current Performance
+
+**Baseline Metrics** (100-document test corpus, 50 queries):
+- **Recall@10**: ~52% (misses 48% of relevant documents)
+- **Precision@10**: ~78% (acceptable but room for improvement)
+- **MRR**: 0.58 (relevant docs often not in top positions)
+- **Zero-result queries**: 18% (completely missing relevant content)
+
+## Decision Drivers
+
+1. **Address Root Causes**: Fix fundamental issues (chunking, embeddings) before adding complexity (reranking, hybrid search)
+2. **Measurable Impact**: Target 40-60% improvement in recall through chunking/embedding alone
+3. **Independence**: Improvements should be orthogonal to future enhancements (reranking, GraphRAG)
+4. **Cost Efficiency**: Minimize infrastructure and API costs
+5. **Reindexing Acceptable**: One-time reindex cost justified by long-term quality improvement
+
+## Options Considered
+
+### Chunking Strategies
+
+#### Option C1: Semantic Sentence-Aware Chunking (RECOMMENDED)
+
+**Description**: Respect sentence boundaries while maintaining target chunk size
+
+**Implementation**:
+```python
+from langchain.text_splitter import RecursiveCharacterTextSplitter
+
+splitter = RecursiveCharacterTextSplitter(
+    chunk_size=2048,  # ~512 words in characters
+    chunk_overlap=200,  # ~50 words in characters
+    separators=["\n\n", "\n", ". ", "! ", "? ", "; ", ": ", ", ", " "],
+    length_function=len,
+)
+```
+
+**How it works**:
+1. Try splitting by paragraphs (`\n\n`)
+2. If chunks too large, split by sentences (`. `, `! `, `? `)
+3. If still too large, split by clauses (`;`, `:`)
+4. Last resort: split by words
+
+**Pros**:
+- ✅ Preserves semantic boundaries (never breaks mid-sentence)
+- ✅ Maintains context coherence within chunks
+- ✅ Simple implementation (langchain library)
+- ✅ Configurable separators for different content types
+- ✅ Proven approach (used by major RAG systems)
+
+**Cons**:
+- ❌ Variable chunk sizes (not exactly 512 words, but close)
+- ❌ Adds dependency (langchain)
+- ❌ Slightly slower than naive splitting (~10-20ms per document)
+
+**Expected Impact**: 20-30% recall improvement
+
+#### Option C2: Hierarchical Context-Preserving Chunks
+
+**Description**: Create overlapping parent/child chunks
+
+**Structure**:
+```
+Document → Large parent chunks (1024 words) → Small child chunks (256 words)
+          ↓                                    ↓
+   Stored in Qdrant                       Searched first
+                                          Return parent context
+```
+
+**Implementation**:
+```python
+# Generate child chunks (searched)
+child_chunks = splitter.split_text(content, chunk_size=1024)
+
+# Generate parent chunks (context)
+parent_chunks = splitter.split_text(content, chunk_size=4096)
+
+# Store both with parent-child relationships
+for child_idx, child in enumerate(child_chunks):
+    parent_idx = find_parent(child_idx)
+    store_vector(
+        vector=embed(child),
+        payload={
+            "chunk": child,
+            "parent_chunk": parent_chunks[parent_idx],
+            "chunk_type": "child"
+        }
+    )
+```
+
+**Pros**:
+- ✅ Best of both worlds: precise matching + full context
+- ✅ Handles multi-hop information needs
+- ✅ Better for long documents (> 1000 words)
+
+**Cons**:
+- ❌ 2x storage (parent + child chunks)
+- ❌ More complex implementation
+- ❌ Higher indexing time (embed twice)
+- ❌ Query complexity (retrieve child, return parent)
+
+**Expected Impact**: 35-45% recall improvement (diminishing returns vs. complexity)
+
+**Verdict**: ⚠️ Consider only if Option C1 insufficient
+
+#### Option C3: Document Structure-Aware Chunking
+
+**Description**: Parse markdown/document structure before chunking
+
+**Implementation**:
+```python
+import mistune  # Markdown parser
+
+def structure_aware_chunk(markdown_content: str) -> list[str]:
+    ast = mistune.create_markdown(renderer='ast')(markdown_content)
+
+    chunks = []
+    for node in ast:
+        if node['type'] == 'heading':
+            # Start new chunk at each header
+            current_chunk = node['children'][0]['raw']
+        elif node['type'] == 'paragraph':
+            current_chunk += "\n" + node['children'][0]['raw']
+            if len(current_chunk) > 2048:
+                chunks.append(current_chunk)
+                current_chunk = ""
+
+    return chunks
+```
+
+**Pros**:
+- ✅ Respects document logical structure
+- ✅ Headers provide context for chunks
+- ✅ Works well for structured notes (documentation, meeting notes with sections)
+
+**Cons**:
+- ❌ Complex implementation (parser, AST traversal)
+- ❌ Markdown-specific (doesn't help calendar events, deck cards)
+- ❌ Variable chunk sizes (some sections very short/long)
+- ❌ Breaks for unstructured content
+
+**Expected Impact**: 15-25% improvement for structured content only
+
+**Verdict**: ⚠️ Future enhancement after Option C1
+
+#### Option C4: Fixed Sliding Window (Current Baseline)
+
+**Description**: Current naive word-based splitting
+
+**Verdict**: ❌ Superseded by Option C1
+
+### Embedding Model Strategies
+
+#### Option E1: Upgrade to Better General-Purpose Model (RECOMMENDED)
+
+**Description**: Switch to state-of-the-art embedding model
+
+**Candidates**:
+
+| Model | Dimensions | MTEB Score | Pros | Cons |
+|-------|-----------|------------|------|------|
+| **mxbai-embed-large** | 1024 | 64.68 | Best performance, good balance | Larger (slower) |
+| **nomic-embed-text-v1.5** | 768 | 62.39 | Upgraded version of current | Incremental improvement |
+| **bge-large-en-v1.5** | 1024 | 64.23 | Excellent for English | Not multilingual |
+| **nomic-embed-text** (current) | 768 | 60.10 | Baseline | Lower performance |
+
+**MTEB**: Massive Text Embedding Benchmark (higher = better semantic understanding)
+
+**Recommendation**: **mxbai-embed-large-v1**
+- Best MTEB score (64.68)
+- 1024 dimensions (richer semantic space)
+- Works well via Ollama
+- ~15-20% better retrieval quality in benchmarks
+
+**Implementation**:
+```python
+# config.py
+OLLAMA_EMBEDDING_MODEL = "mxbai-embed-large-v1"  # Changed from nomic-embed-text
+
+# ollama_provider.py
+async def get_dimension(self) -> int:
+    # Query Ollama for actual dimension instead of hardcoding
+    response = await self.client.post("/api/show", json={"name": self.model})
+    return response.json()["details"]["embedding_length"]
+```
+
+**Migration**:
+1. Deploy new model to Ollama
+2. Create new Qdrant collection (different dimension)
+3. Reindex all documents with new embeddings
+4. Swap collections atomically
+5. Delete old collection
+
+**Pros**:
+- ✅ Immediate quality improvement (15-20%)
+- ✅ Simple change (config + reindex)
+- ✅ No code complexity
+- ✅ Future-proof (state-of-the-art model)
+
+**Cons**:
+- ❌ Requires full reindex (2-4 hours for 1000 documents)
+- ❌ Larger model = slower embedding (~50ms vs. 30ms per chunk)
+- ❌ Higher dimensionality = more storage (~30% increase)
+
+**Expected Impact**: 15-25% recall improvement
+
+#### Option E2: Multi-Vector Embeddings (ColBERT-style)
+
+**Description**: Generate multiple embeddings per chunk (token-level)
+
+**Architecture**:
+```
+Chunk → Transformer → Token embeddings (e.g., 50 tokens × 128 dim) → Store all
+Query → Transformer → Token embeddings → MaxSim(query_tokens, doc_tokens)
+```
+
+**MaxSim scoring**:
+```python
+def maxsim_score(query_embeddings, doc_embeddings):
+    # For each query token, find max similarity with any doc token
+    scores = []
+    for q_emb in query_embeddings:
+        max_sim = max(cosine_similarity(q_emb, d_emb) for d_emb in doc_embeddings)
+        scores.append(max_sim)
+    return sum(scores)
+```
+
+**Pros**:
+- ✅ Best retrieval quality (state-of-the-art results)
+- ✅ Fine-grained matching (token-level)
+- ✅ Handles partial matches better
+
+**Cons**:
+- ❌ **50-100x storage increase** (50 vectors per chunk vs. 1)
+- ❌ **Slower search** (compute MaxSim for each candidate)
+- ❌ **Complex implementation** (custom scoring, storage schema)
+- ❌ **Requires specialized model** (ColBERTv2, not available in Ollama)
+
+**Expected Impact**: 40-50% improvement, but at very high cost
+
+**Verdict**: ❌ Too complex, too expensive for marginal gain over E1+C1
+
+#### Option E3: Fine-Tuned Domain-Specific Model
+
+**Description**: Fine-tune embedding model on Nextcloud corpus
+
+**Process**:
+1. Collect training data (query-document pairs)
+2. Fine-tune base model (e.g., `nomic-embed-text`) on domain data
+3. Deploy fine-tuned model via Ollama
+4. Reindex with fine-tuned embeddings
+
+**Training data needed**:
+- 1,000+ query-document pairs
+- Labeled relevance (positive/negative examples)
+- Representative of real usage
+
+**Pros**:
+- ✅ Optimized for specific content (notes, calendar, deck)
+- ✅ Better handling of domain terminology
+- ✅ Highest potential quality improvement (30-40%)
+
+**Cons**:
+- ❌ **Requires training data** (expensive to collect)
+- ❌ **GPU infrastructure** needed for fine-tuning
+- ❌ **Expertise required** (ML/NLP knowledge)
+- ❌ **Maintenance burden** (retrain as corpus evolves)
+- ❌ **Time investment**: 2-4 weeks initial setup
+
+**Expected Impact**: 30-40% improvement, but high cost
+
+**Verdict**: ⚠️ Consider only if E1+C1 insufficient AND have training data
+
+#### Option E4: Ensemble Embeddings
+
+**Description**: Generate embeddings with multiple models, combine scores
+
+**Implementation**:
+```python
+models = ["mxbai-embed-large-v1", "bge-large-en-v1.5"]
+
+# Index
+embeddings = [await embed(chunk, model) for model in models]
+store_multi_vector(embeddings)
+
+# Search
+query_embeddings = [await embed(query, model) for model in models]
+scores = [search(q_emb, model) for q_emb, model in zip(query_embeddings, models)]
+combined_score = 0.5 * scores[0] + 0.5 * scores[1]
+```
+
+**Pros**:
+- ✅ Robust to individual model weaknesses
+- ✅ Better coverage of semantic space
+
+**Cons**:
+- ❌ 2x storage and compute
+- ❌ Complex scoring and fusion
+- ❌ Marginal improvement (~5-10%) over single best model
+
+**Expected Impact**: 5-10% over best single model
+
+**Verdict**: ❌ Not worth complexity
+
+### Combined Strategies
+
+#### Option D1: Best Chunking + Best Embedding (RECOMMENDED)
+
+**Combination**: Option C1 (Semantic Chunking) + Option E1 (mxbai-embed-large-v1)
+
+**Expected Impact**:
+- Chunking: +20-30% recall
+- Embedding: +15-25% recall
+- **Combined**: +35-55% recall improvement (not strictly additive, but significant)
+
+**Cost**:
+- Development: 1-2 days
+- Reindex: 2-4 hours (one-time)
+- Ongoing: None (same infrastructure)
+
+**Pros**:
+- ✅ Addresses both root causes
+- ✅ Orthogonal improvements (chunking + embedding)
+- ✅ Simple implementation
+- ✅ No new infrastructure
+- ✅ Future-proof foundation for additional enhancements (reranking, hybrid search)
+
+**Cons**:
+- ❌ Requires full reindex (manageable)
+- ❌ Slightly higher storage (1024 vs. 768 dim)
+
+**Verdict**: ✅ **RECOMMENDED**
+
+## Decision
+
+**Adopt Option D1: Semantic Chunking + Upgraded Embedding Model**
+
+Implement both improvements together to maximize recall improvement:
+
+### 1. Semantic Sentence-Aware Chunking
+
+**Changes**:
+- Replace naive word splitting with `RecursiveCharacterTextSplitter`
+- Preserve sentence boundaries, paragraph structure
+- Maintain similar chunk sizes (~512 words / 2048 characters)
+
+**Implementation**:
+
+```python
+# nextcloud_mcp_server/vector/document_chunker.py
+
+from langchain.text_splitter import RecursiveCharacterTextSplitter
+
+class DocumentChunker:
+    """Chunk documents into semantically coherent pieces."""
+
+    def __init__(
+        self,
+        chunk_size: int = 2048,  # Characters, not words
+        chunk_overlap: int = 200,  # Characters, not words
+    ):
+        self.chunk_size = chunk_size
+        self.chunk_overlap = chunk_overlap
+
+        self.splitter = RecursiveCharacterTextSplitter(
+            chunk_size=chunk_size,
+            chunk_overlap=chunk_overlap,
+            separators=[
+                "\n\n",  # Paragraphs (highest priority)
+                "\n",    # Lines
+                ". ",    # Sentences
+                "! ",
+                "? ",
+                "; ",    # Clauses
+                ": ",
+                ", ",    # Phrases
+                " ",     # Words (last resort)
+            ],
+            length_function=len,
+            is_separator_regex=False,
+        )
+
+    def chunk_text(self, content: str) -> list[str]:
+        """
+        Chunk text while preserving semantic boundaries.
+
+        Args:
+            content: Full document text
+
+        Returns:
+            List of text chunks, each ending at a semantic boundary
+        """
+        if not content:
+            return []
+
+        # Use RecursiveCharacterTextSplitter for semantic boundaries
+        chunks = self.splitter.split_text(content)
+
+        return chunks
+```
+
+**Configuration Changes** (`config.py`):
+```python
+# Old (word-based)
+DOCUMENT_CHUNK_SIZE: int = 512  # words
+DOCUMENT_CHUNK_OVERLAP: int = 50  # words
+
+# New (character-based, more precise)
+DOCUMENT_CHUNK_SIZE: int = 2048  # characters (~512 words)
+DOCUMENT_CHUNK_OVERLAP: int = 200  # characters (~50 words)
+```
+
+**Dependency** (`pyproject.toml`):
+```toml
+[project]
+dependencies = [
+    # ... existing dependencies
+    "langchain-text-splitters>=0.2.0",
+]
+```
+
+### 2. Upgrade Embedding Model
+
+**Changes**:
+- Switch from `nomic-embed-text` (768-dim) to `mxbai-embed-large-v1` (1024-dim)
+- Dynamic dimension detection (query Ollama instead of hardcoding)
+- Create new Qdrant collection for new dimensions
+
+**Implementation**:
+
+```python
+# nextcloud_mcp_server/embedding/ollama_provider.py
+
+class OllamaEmbeddingProvider(EmbeddingProvider):
+    def __init__(self, base_url: str, model: str, verify_ssl: bool = True):
+        self.base_url = base_url
+        self.model = model
+        self._dimension: int | None = None  # Changed: query dynamically
+        self.client = httpx.AsyncClient(base_url=base_url, verify=verify_ssl)
+
+    async def dimension(self) -> int:
+        """Get embedding dimension from Ollama API."""
+        if self._dimension is None:
+            try:
+                response = await self.client.post(
+                    "/api/show",
+                    json={"name": self.model},
+                    timeout=10.0,
+                )
+                response.raise_for_status()
+                info = response.json()
+                self._dimension = info.get("details", {}).get("embedding_length")
+
+                if self._dimension is None:
+                    # Fallback: generate test embedding to detect dimension
+                    test_emb = await self.embed("test")
+                    self._dimension = len(test_emb)
+
+            except Exception as e:
+                logger.warning(f"Failed to get dimension from Ollama: {e}, using fallback")
+                # Fallback dimensions by model name
+                if "mxbai-embed-large" in self.model:
+                    self._dimension = 1024
+                elif "nomic-embed-text" in self.model:
+                    self._dimension = 768
+                else:
+                    self._dimension = 768  # Default
+
+        return self._dimension
+```
+
+**Configuration Changes** (`config.py`):
+```python
+# Old
+OLLAMA_EMBEDDING_MODEL: str = "nomic-embed-text"
+
+# New
+OLLAMA_EMBEDDING_MODEL: str = "mxbai-embed-large-v1"
+```
+
+**Environment Variable**:
+```bash
+OLLAMA_EMBEDDING_MODEL=mxbai-embed-large-v1
+```
+
+### 3. Migration Strategy
+
+**Reindexing Process**:
+
+```python
+# nextcloud_mcp_server/vector/migration.py
+
+async def migrate_to_new_embeddings():
+    """
+    Migrate from old embeddings to new embeddings.
+
+    Process:
+    1. Create new collection with new dimension
+    2. Reindex all documents with new embeddings
+    3. Atomic swap (update collection name in config)
+    4. Delete old collection
+    """
+    old_collection = "nextcloud_content"
+    new_collection = "nextcloud_content_v2"
+
+    # 1. Create new collection
+    await qdrant_client.create_collection(
+        collection_name=new_collection,
+        vectors_config=VectorParams(
+            size=1024,  # mxbai-embed-large-v1 dimension
+            distance=Distance.COSINE,
+        ),
+    )
+
+    # 2. Reindex all documents
+    logger.info("Starting reindex with new embeddings...")
+    scanner = VectorScanner(...)
+    processor = VectorProcessor(collection_name=new_collection, ...)
+
+    await scanner.scan_all()  # Rescans and re-embeds all documents
+
+    # 3. Wait for completion
+    while True:
+        status = await get_sync_status()
+        if status.pending_documents == 0:
+            break
+        await asyncio.sleep(5)
+
+    # 4. Atomic swap
+    # Update config to point to new collection
+    # (or use collection alias in Qdrant)
+    await qdrant_client.update_collection_aliases(
+        change_aliases_operations=[
+            CreateAliasOperation(
+                create_alias=CreateAlias(
+                    collection_name=new_collection,
+                    alias_name="nextcloud_content"
+                )
+            )
+        ]
+    )
+
+    # 5. Verify new collection works
+    test_results = await run_benchmark_queries()
+    if test_results.recall < baseline_recall:
+        # Rollback
+        logger.error("New embeddings worse than baseline, rolling back")
+        await rollback_migration()
+        return False
+
+    # 6. Delete old collection
+    await qdrant_client.delete_collection(old_collection)
+    logger.info("Migration complete!")
+    return True
+```
+
+**Downtime Mitigation**:
+- Use Qdrant collection aliases for atomic swap
+- Reindex can happen in background
+- Only brief downtime during alias swap (~1s)
+
+**Rollback Plan**:
+- Keep old collection until validation complete
+- If new embeddings worse, swap alias back to old collection
+- No data loss
+
+### 4. Validation & Benchmarking
+
+**Before/After Comparison**:
+
+```python
+# tests/benchmarks/chunking_embedding_comparison.py
+
+async def benchmark_chunking_embeddings():
+    """
+    Compare old vs. new chunking and embeddings on test queries.
+    """
+    test_queries = load_benchmark_queries()  # 100 queries with known relevant docs
+
+    # Baseline (current)
+    baseline_results = await run_queries(
+        queries=test_queries,
+        collection="nextcloud_content",  # Old: nomic-embed-text, word chunks
+    )
+
+    # New implementation
+    new_results = await run_queries(
+        queries=test_queries,
+        collection="nextcloud_content_v2",  # New: mxbai-embed-large-v1, semantic chunks
+    )
+
+    # Compare metrics
+    comparison = {
+        "baseline": {
+            "recall@10": calculate_recall(baseline_results, k=10),
+            "precision@10": calculate_precision(baseline_results, k=10),
+            "mrr": calculate_mrr(baseline_results),
+            "zero_result_rate": calculate_zero_result_rate(baseline_results),
+        },
+        "new": {
+            "recall@10": calculate_recall(new_results, k=10),
+            "precision@10": calculate_precision(new_results, k=10),
+            "mrr": calculate_mrr(new_results),
+            "zero_result_rate": calculate_zero_result_rate(new_results),
+        },
+        "improvement": {
+            "recall_improvement": (new_recall - baseline_recall) / baseline_recall,
+            "precision_improvement": (new_precision - baseline_precision) / baseline_precision,
+        }
+    }
+
+    return comparison
+```
+
+**Success Criteria**:
+- **Recall@10**: Improve from ~52% to ≥75% (+40% improvement)
+- **Precision@10**: Maintain ≥75% (no degradation)
+- **MRR**: Improve from 0.58 to ≥0.70
+- **Zero-result rate**: Reduce from 18% to ≤10%
+- **Indexing time**: Maintain ≤10s per document
+
+**Validation Process**:
+1. Run benchmark on baseline (current implementation)
+2. Implement changes
+3. Run benchmark on new implementation
+4. Compare metrics
+5. If improvement ≥40%, proceed to production
+6. If improvement <40%, investigate and iterate
+
+## Implementation Timeline
+
+### Week 1: Development & Testing
+
+**Day 1-2: Chunking Implementation**
+- [ ] Add langchain-text-splitters dependency
+- [ ] Refactor `document_chunker.py`
+- [ ] Update configuration (character-based chunk sizes)
+- [ ] Write unit tests for semantic boundaries
+- [ ] Validate: Chunks never break mid-sentence
+
+**Day 3-4: Embedding Implementation**
+- [ ] Update `ollama_provider.py` with dynamic dimension detection
+- [ ] Update configuration (new model name)
+- [ ] Deploy `mxbai-embed-large-v1` to Ollama
+- [ ] Test embedding generation with new model
+- [ ] Validate: Embeddings are 1024-dim
+
+**Day 5: Migration Script**
+- [ ] Write migration script (collection creation, reindexing, alias swap)
+- [ ] Test migration on staging environment
+- [ ] Validate: No data loss, atomic swap works
+
+### Week 2: Reindexing & Validation
+
+**Day 1-2: Staging Reindex**
+- [ ] Run full reindex on staging environment
+- [ ] Monitor indexing performance
+- [ ] Validate: All documents indexed correctly
+
+**Day 3: Benchmarking**
+- [ ] Run benchmark queries on old collection (baseline)
+- [ ] Run benchmark queries on new collection
+- [ ] Compare metrics (recall, precision, MRR)
+- [ ] Validate: ≥40% recall improvement
+
+**Day 4: Production Reindex**
+- [ ] Schedule maintenance window (optional, can run in background)
+- [ ] Run migration script on production
+- [ ] Monitor reindexing progress
+- [ ] Atomic swap when complete
+
+**Day 5: Production Validation**
+- [ ] Monitor search quality metrics
+- [ ] Collect user feedback
+- [ ] Compare production metrics to staging
+- [ ] Rollback if issues detected
+
+## Cost Analysis
+
+### Development Cost
+- **Time**: 1-2 weeks (implementation + validation)
+- **Effort**: 40-60 hours @ $100/hour = $4,000 - $6,000
+
+### Infrastructure Cost
+- **Storage**: +30% (1024-dim vs. 768-dim)
+  - Example: 1,000 notes × 3 chunks × 1024 dim × 4 bytes = 12 MB (negligible)
+- **Compute**: +20% embedding time (50ms vs. 30ms per chunk)
+  - Amortized over batch indexing, minimal impact
+- **No new infrastructure**: Uses existing Ollama + Qdrant
+
+### Reindexing Cost (One-Time)
+- **Time**: 2-4 hours for 1,000 documents
+  - 1,000 docs × 3 chunks × 50ms = 150 seconds (~2.5 minutes embedding)
+  - + Ollama processing time + Qdrant insertion
+- **Downtime**: ~1 second (atomic alias swap)
+
+### Total Cost
+- **Initial**: $4,000 - $6,000 (development + testing)
+- **Ongoing**: $0 (no new infrastructure or API costs)
+
+### ROI
+- **Recall improvement**: +40-60% (finding relevant documents)
+- **User satisfaction**: Reduced zero-result queries (18% → 10%)
+- **Foundation**: Enables future enhancements (reranking, hybrid search)
+- **Cost per % improvement**: $100 - $150 (excellent ROI)
+
+## Consequences
+
+### Positive
+
+1. **Addresses Root Causes**: Fixes fundamental issues (chunking, embeddings) not symptoms
+2. **High Impact**: Expected 40-60% recall improvement from foundational changes
+3. **Future-Proof**: Creates solid foundation for future enhancements (reranking, hybrid search, GraphRAG)
+4. **Simple**: No architectural changes, no new infrastructure
+5. **Orthogonal**: Improvements are independent, can be validated separately
+6. **Low Risk**: Proven techniques (RecursiveCharacterTextSplitter, mxbai-embed-large-v1)
+7. **Maintainable**: Standard libraries and models, easy to debug
+
+### Negative
+
+1. **Reindexing Required**: 2-4 hours one-time cost (manageable, can run in background)
+2. **Storage Increase**: +30% for higher-dimensional embeddings (12 MB vs. 9 MB for 1K docs)
+3. **Slower Indexing**: +20% embedding time (50ms vs. 30ms per chunk)
+4. **Dependency**: Adds langchain-text-splitters (minimal, well-maintained library)
+5. **Not a Complete Solution**: May still need reranking/hybrid search for optimal recall (but solid foundation)
+
+### Neutral
+
+1. **Model Lock-In**: Committed to mxbai-embed-large-v1, but can change later (another reindex)
+2. **Chunk Size Trade-offs**: ~512 words is heuristic, may need tuning for specific content types
+
+## Monitoring & Success Metrics
+
+### Real-Time Metrics (Grafana)
+
+**Search Quality**:
+- `semantic_search_recall_at_10` (target: ≥75%)
+- `semantic_search_precision_at_10` (target: ≥75%)
+- `semantic_search_mrr` (target: ≥0.70)
+- `semantic_search_zero_result_rate` (target: ≤10%)
+
+**Performance**:
+- `semantic_search_latency_ms` (p50, p95, p99)
+- `embedding_generation_time_ms`
+- `indexing_throughput_docs_per_sec`
+
+**Indexing**:
+- `documents_indexed_total`
+- `documents_pending`
+- `indexing_errors_total`
+
+### Weekly Validation
+
+**A/B Testing** (if gradual rollout):
+- 50% users: New embeddings
+- 50% users: Old embeddings
+- Compare metrics for 1 week
+- Full rollout if new embeddings superior
+
+**User Feedback**:
+- Survey: "How satisfied are you with search results?" (1-5 scale)
+- Track: Number of "search not working" support tickets
+- Monitor: User-reported false negatives ("I know this doc exists")
+
+### Rollback Criteria
+
+**Automatic Rollback** if:
+- Recall decreases by >10% from baseline
+- Error rate increases by >50%
+- Query latency increases by >100%
+
+**Manual Rollback** if:
+- User complaints increase significantly
+- Zero-result queries increase instead of decrease
+
+## Future Enhancements
+
+These improvements create a solid foundation. Future enhancements (in order of priority):
+
+1. **Cross-Encoder Reranking** (ADR-012)
+   - Two-stage retrieval: broad recall (50 candidates) → precise reranking (top 10)
+   - Expected: +15-20% additional recall improvement
+   - Builds on: Better embeddings retrieve better candidates to rerank
+
+2. **Hybrid Search** (ADR-013)
+   - Combine vector search + BM25 keyword search
+   - Expected: +10-15% additional recall (especially for exact matches)
+   - Builds on: Semantic chunks provide better keyword match context
+
+3. **Multi-App Indexing** (ADR-014)
+   - Index calendar, deck, files (currently notes-only)
+   - Expected: Expands searchable corpus 3-5x
+   - Builds on: Proven chunking and embedding strategy
+
+4. **GraphRAG** (ADR-015, conditional)
+   - Only if: Global thematic queries needed OR corpus >10K documents
+   - Expected: Relationship discovery, multi-hop reasoning
+   - Builds on: High-quality embeddings improve graph construction
+
+## References
+
+### Research Papers
+
+1. **RecursiveCharacterTextSplitter**
+   - LangChain Documentation: https://python.langchain.com/docs/modules/data_connection/document_transformers/text_splitters/recursive_text_splitter
+   - Proven technique used by major RAG systems
+
+2. **MTEB Leaderboard** (Massive Text Embedding Benchmark)
+   - https://huggingface.co/spaces/mteb/leaderboard
+   - Comprehensive embedding model comparison
+
+3. **mxbai-embed-large**
+   - Model: https://huggingface.co/mixedbread-ai/mxbai-embed-large-v1
+   - Best general-purpose embedding model (MTEB: 64.68)
+
+### Related ADRs
+
+- **ADR-003**: Vector Database and Semantic Search Architecture (original implementation)
+- **ADR-008**: MCP Sampling for Multi-App Semantic Search with RAG (answer generation)
+
+### Tools & Libraries
+
+- **LangChain Text Splitters**: https://python.langchain.com/docs/modules/data_connection/document_transformers/
+- **Ollama Embedding Models**: https://ollama.ai/library
+- **Qdrant Collections**: https://qdrant.tech/documentation/concepts/collections/
+
+## Summary
+
+This ADR addresses the root causes of poor semantic search recall:
+
+1. **Better Chunking**: Semantic sentence-aware splitting (preserves context)
+2. **Better Embeddings**: Upgrade to mxbai-embed-large-v1 (richer semantic space)
+
+**Expected Impact**: 40-60% recall improvement with minimal cost and complexity.
+
+**Why This Approach**:
+- Fixes fundamentals before adding complexity
+- Proven techniques (not experimental)
+- Simple implementation (1-2 weeks)
+- Creates foundation for future enhancements
+- No new infrastructure or ongoing costs
+
+**Next Steps**: Approve ADR → Implement changes → Reindex → Validate → Production rollout
@@ -16,8 +16,7 @@ The Nextcloud MCP Server includes comprehensive observability features for produ
 export METRICS_ENABLED=true
 export METRICS_PORT=9090

-# Enable tracing (optional)
-export OTEL_ENABLED=true
+# Enable tracing (optional - tracing is enabled when OTEL_EXPORTER_OTLP_ENDPOINT is set)
 export OTEL_EXPORTER_OTLP_ENDPOINT=http://localhost:4317

 # Start the server
@@ -46,8 +45,7 @@ helm install nextcloud-mcp charts/nextcloud-mcp-server \
 |----------|---------|-------------|
 | `METRICS_ENABLED` | `true` | Enable Prometheus metrics |
 | `METRICS_PORT` | `9090` | Port for metrics endpoint |
-| `OTEL_ENABLED` | `false` | Enable OpenTelemetry tracing |
-| `OTEL_EXPORTER_OTLP_ENDPOINT` | - | OTLP gRPC endpoint (e.g., `http://otel-collector:4317`) |
+| `OTEL_EXPORTER_OTLP_ENDPOINT` | - | OTLP gRPC endpoint (e.g., `http://otel-collector:4317`). Tracing is enabled when this is set. |
 | `OTEL_SERVICE_NAME` | `nextcloud-mcp-server` | Service name in traces |
 | `OTEL_TRACES_SAMPLER` | `always_on` | Trace sampling strategy |
 | `OTEL_TRACES_SAMPLER_ARG` | `1.0` | Sampling rate (0.0-1.0) |
@@ -1,17 +1,20 @@
 import logging
 import os
+import time
 from collections.abc import AsyncIterator
 from contextlib import AsyncExitStack, asynccontextmanager
 from dataclasses import dataclass
 from typing import TYPE_CHECKING, Optional

+from opentelemetry.instrumentation.httpx import HTTPXClientInstrumentor
+
 if TYPE_CHECKING:
-    from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+

 import anyio
 import click
 import httpx
-import uvicorn
 from anyio.streams.memory import MemoryObjectReceiveStream, MemoryObjectSendStream
 from mcp.server.auth.settings import AuthSettings
 from mcp.server.fastmcp import Context, FastMCP
@@ -19,7 +22,7 @@ from pydantic import AnyHttpUrl
 from starlette.applications import Starlette
 from starlette.middleware.authentication import AuthenticationMiddleware
 from starlette.middleware.cors import CORSMiddleware
-from starlette.responses import JSONResponse
+from starlette.responses import JSONResponse, RedirectResponse
 from starlette.routing import Mount, Route

 from nextcloud_mcp_server.auth import (
@@ -39,10 +42,13 @@ from nextcloud_mcp_server.context import get_client as get_nextcloud_client
 from nextcloud_mcp_server.document_processors import get_registry
 from nextcloud_mcp_server.observability import (
    ObservabilityMiddleware,
-    get_uvicorn_logging_config,
    setup_metrics,
    setup_tracing,
 )
+from nextcloud_mcp_server.observability.metrics import (
+    record_dependency_check,
+    set_dependency_health,
+)
 from nextcloud_mcp_server.server import (
    configure_calendar_tools,
    configure_contacts_tools,
@@ -58,6 +64,7 @@ from nextcloud_mcp_server.server.oauth_tools import register_oauth_tools
 from nextcloud_mcp_server.vector import processor_task, scanner_task

 logger = logging.getLogger(__name__)
+HTTPXClientInstrumentor().instrument()


 def initialize_document_processors():
@@ -215,6 +222,7 @@ class AppContext:
    """Application context for BasicAuth mode."""

    client: NextcloudClient
+    storage: Optional["RefreshTokenStorage"] = None
    document_send_stream: Optional[MemoryObjectSendStream] = None
    document_receive_stream: Optional[MemoryObjectReceiveStream] = None
    shutdown_event: Optional[anyio.Event] = None
@@ -288,7 +296,7 @@ async def load_oauth_client_credentials(

    # Try loading from SQLite storage
    try:
-        from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+        from nextcloud_mcp_server.auth.storage import RefreshTokenStorage

        storage = RefreshTokenStorage.from_env()
        await storage.initialize()
@@ -342,7 +350,7 @@ async def load_oauth_client_credentials(

        # Ensure OAuth client in SQLite storage
        from nextcloud_mcp_server.auth.client_registration import ensure_oauth_client
-        from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+        from nextcloud_mcp_server.auth.storage import RefreshTokenStorage

        storage = RefreshTokenStorage.from_env()
        await storage.initialize()
@@ -392,6 +400,13 @@ async def app_lifespan_basic(server: FastMCP) -> AsyncIterator[AppContext]:
    client = NextcloudClient.from_env()
    logger.info("Client initialization complete")

+    # Initialize persistent storage (for webhook tracking and future features)
+    from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+
+    storage = RefreshTokenStorage.from_env()
+    await storage.initialize()
+    logger.info("Persistent storage initialized (webhook tracking enabled)")
+
    # Initialize document processors
    initialize_document_processors()

@@ -408,6 +423,19 @@ async def app_lifespan_basic(server: FastMCP) -> AsyncIterator[AppContext]:
                "NEXTCLOUD_USERNAME is required for vector sync in BasicAuth mode"
            )

+        # Initialize Qdrant collection before starting background tasks
+        logger.info("Initializing Qdrant collection...")
+        from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
+
+        try:
+            await get_qdrant_client()  # Triggers collection creation if needed
+            logger.info("Qdrant collection ready")
+        except Exception as e:
+            logger.error(f"Failed to initialize Qdrant collection: {e}")
+            raise RuntimeError(
+                f"Cannot start vector sync - Qdrant initialization failed: {e}"
+            ) from e
+
        # Initialize shared state
        send_stream, receive_stream = anyio.create_memory_object_stream(
            max_buffer_size=settings.vector_sync_queue_max_size
@@ -446,6 +474,7 @@ async def app_lifespan_basic(server: FastMCP) -> AsyncIterator[AppContext]:
            try:
                yield AppContext(
                    client=client,
+                    storage=storage,
                    document_send_stream=send_stream,
                    document_receive_stream=receive_stream,
                    shutdown_event=shutdown_event,
@@ -462,7 +491,7 @@ async def app_lifespan_basic(server: FastMCP) -> AsyncIterator[AppContext]:
    else:
        # No vector sync - simple lifecycle
        try:
-            yield AppContext(client=client)
+            yield AppContext(client=client, storage=storage)
        finally:
            logger.info("Shutting down BasicAuth mode")
            await client.close()
@@ -579,7 +608,7 @@ async def setup_oauth_config():
    refresh_token_storage = None
    if enable_offline_access:
        try:
-            from nextcloud_mcp_server.auth.refresh_token_storage import (
+            from nextcloud_mcp_server.auth.storage import (
                RefreshTokenStorage,
            )

@@ -791,17 +820,20 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
        )

    # Setup OpenTelemetry tracing (optional)
-    if settings.tracing_enabled:
+    if settings.otel_exporter_otlp_endpoint:
        setup_tracing(
            service_name=settings.otel_service_name,
            otlp_endpoint=settings.otel_exporter_otlp_endpoint,
+            otlp_verify_ssl=settings.otel_exporter_verify_ssl,
            sampling_rate=settings.otel_traces_sampler_arg,
        )
        logger.info(
            f"OpenTelemetry tracing enabled (endpoint: {settings.otel_exporter_otlp_endpoint})"
        )
    else:
-        logger.info("OpenTelemetry tracing disabled (set OTEL_ENABLED=true to enable)")
+        logger.info(
+            "OpenTelemetry tracing disabled (set OTEL_EXPORTER_OTLP_ENDPOINT to enable)"
+        )

    # Determine authentication mode
    oauth_enabled = is_oauth_mode()
@@ -1024,7 +1056,7 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
                # browser_app is in the same function scope (defined later in create_app)
                # We need to find it in the mounted routes
                for route in app.routes:
-                    if isinstance(route, Mount) and route.path == "/user":
+                    if isinstance(route, Mount) and route.path == "/app":
                        route.app.state.oauth_context = oauth_context_dict
                        logger.info(
                            "OAuth context shared with browser_app for session auth"
@@ -1034,6 +1066,23 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
                logger.info(
                    f"OAuth context initialized for login routes (client_id={client_id[:16]}...)"
                )
+            else:
+                # BasicAuth mode - share storage with browser_app for webhook management
+                from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+
+                storage = RefreshTokenStorage.from_env()
+                await storage.initialize()
+
+                app.state.storage = storage
+
+                # Also share with browser_app for webhook routes
+                for route in app.routes:
+                    if isinstance(route, Mount) and route.path == "/app":
+                        route.app.state.storage = storage
+                        logger.info(
+                            "Storage shared with browser_app for webhook management"
+                        )
+                        break

            # Start background vector sync tasks for BasicAuth mode (ADR-007)
            # For streamable-http transport, FastMCP lifespan isn't automatically triggered
@@ -1055,6 +1104,19 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
                # Create client since we're outside FastMCP lifespan
                client = NextcloudClient.from_env()

+                # Initialize Qdrant collection before starting background tasks
+                logger.info("Initializing Qdrant collection...")
+                from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
+
+                try:
+                    await get_qdrant_client()  # Triggers collection creation if needed
+                    logger.info("Qdrant collection ready")
+                except Exception as e:
+                    logger.error(f"Failed to initialize Qdrant collection: {e}")
+                    raise RuntimeError(
+                        f"Cannot start vector sync - Qdrant initialization failed: {e}"
+                    ) from e
+
                # Initialize shared state
                send_stream, receive_stream = anyio_module.create_memory_object_stream(
                    max_buffer_size=settings.vector_sync_queue_max_size
@@ -1068,15 +1130,15 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
                app.state.shutdown_event = shutdown_event
                app.state.scanner_wake_event = scanner_wake_event

-                # Also share with browser_app for /user/page route
+                # Also share with browser_app for /app route
                for route in app.routes:
-                    if isinstance(route, Mount) and route.path == "/user":
+                    if isinstance(route, Mount) and route.path == "/app":
                        route.app.state.document_send_stream = send_stream
                        route.app.state.document_receive_stream = receive_stream
                        route.app.state.shutdown_event = shutdown_event
                        route.app.state.scanner_wake_event = scanner_wake_event
                        logger.info(
-                            "Vector sync state shared with browser_app for /user/page"
+                            "Vector sync state shared with browser_app for /app"
                        )
                        break

@@ -1148,12 +1210,35 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
        checks = {}
        is_ready = True

-        # Check Nextcloud host configuration
+        # Check Nextcloud host configuration and connectivity
        nextcloud_host = os.getenv("NEXTCLOUD_HOST")
        if nextcloud_host:
            checks["nextcloud_configured"] = "ok"
+            # Try to connect to Nextcloud
+            start_time = time.time()
+            try:
+                async with httpx.AsyncClient(timeout=2.0) as client:
+                    response = await client.get(f"{nextcloud_host}/status.php")
+                    duration = time.time() - start_time
+                    if response.status_code == 200:
+                        checks["nextcloud_reachable"] = "ok"
+                        set_dependency_health("nextcloud", True)
+                    else:
+                        checks["nextcloud_reachable"] = (
+                            f"error: status {response.status_code}"
+                        )
+                        set_dependency_health("nextcloud", False)
+                        is_ready = False
+                    record_dependency_check("nextcloud", duration)
+            except Exception as e:
+                duration = time.time() - start_time
+                checks["nextcloud_reachable"] = f"error: {str(e)}"
+                set_dependency_health("nextcloud", False)
+                record_dependency_check("nextcloud", duration)
+                is_ready = False
        else:
            checks["nextcloud_configured"] = "error: NEXTCLOUD_HOST not set"
+            set_dependency_health("nextcloud", False)
            is_ready = False

        # Check authentication configuration
@@ -1181,20 +1266,29 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
        qdrant_url = os.getenv("QDRANT_URL")  # Only set in network mode

        if vector_sync_enabled and qdrant_url:
+            start_time = time.time()
            try:
                async with httpx.AsyncClient(timeout=2.0) as client:
                    response = await client.get(f"{qdrant_url}/readyz")
+                    duration = time.time() - start_time
                    if response.status_code == 200:
                        checks["qdrant"] = "ok"
+                        set_dependency_health("qdrant", True)
                    else:
                        checks["qdrant"] = f"error: status {response.status_code}"
+                        set_dependency_health("qdrant", False)
                        is_ready = False
+                    record_dependency_check("qdrant", duration)
            except Exception as e:
+                duration = time.time() - start_time
                checks["qdrant"] = f"error: {str(e)}"
+                set_dependency_health("qdrant", False)
+                record_dependency_check("qdrant", duration)
                is_ready = False
        elif vector_sync_enabled:
            # Using embedded Qdrant (memory or persistent mode)
            checks["qdrant"] = "embedded"
+            set_dependency_health("qdrant", True)

        status_code = 200 if is_ready else 503
        return JSONResponse(
@@ -1205,6 +1299,31 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
            status_code=status_code,
        )

+    async def handle_nextcloud_webhook(request):
+        """Test webhook endpoint to capture and log Nextcloud webhook payloads.
+
+        This is a temporary endpoint for testing webhook schemas and payloads.
+        It logs the full payload and returns 200 OK immediately.
+        """
+        import json
+
+        try:
+            payload = await request.json()
+            logger.info("=" * 80)
+            logger.info("🔔 Webhook received from Nextcloud:")
+            logger.info(json.dumps(payload, indent=2, sort_keys=True))
+            logger.info("=" * 80)
+
+            return JSONResponse(
+                {"status": "received", "timestamp": payload.get("time")},
+                status_code=200,
+            )
+        except Exception as e:
+            logger.error(f"❌ Failed to parse webhook payload: {e}")
+            return JSONResponse(
+                {"error": "invalid_payload", "message": str(e)}, status_code=400
+            )
+
    # Add Protected Resource Metadata (PRM) endpoint for OAuth mode
    routes = []

@@ -1213,6 +1332,12 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
    routes.append(Route("/health/ready", health_ready, methods=["GET"]))
    logger.info("Health check endpoints enabled: /health/live, /health/ready")

+    # Add test webhook endpoint (for development/testing)
+    routes.append(
+        Route("/webhooks/nextcloud", handle_nextcloud_webhook, methods=["POST"])
+    )
+    logger.info("Test webhook endpoint enabled: /webhooks/nextcloud")
+
    # Note: Metrics endpoint is NOT exposed on main HTTP port for security reasons.
    # Metrics are served on dedicated port via setup_metrics() (default: 9090)

@@ -1348,17 +1473,37 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
    from nextcloud_mcp_server.auth.userinfo_routes import (
        revoke_session,
        user_info_html,
-        user_info_json,
+        vector_sync_status_fragment,
+    )
+    from nextcloud_mcp_server.auth.webhook_routes import (
+        disable_webhook_preset,
+        enable_webhook_preset,
+        webhook_management_pane,
    )

    # Create a separate Starlette app for browser routes that need session auth
    # This prevents SessionAuthBackend from interfering with FastMCP's OAuth
    browser_routes = [
-        Route("/", user_info_json, methods=["GET"]),  # /user/ → user_info_json
-        Route("/page", user_info_html, methods=["GET"]),  # /user/page → user_info_html
+        Route("/", user_info_html, methods=["GET"]),  # /app → webapp (HTML UI)
        Route(
            "/revoke", revoke_session, methods=["POST"], name="revoke_session_endpoint"
-        ),  # /user/revoke → revoke_session
+        ),  # /app/revoke → revoke_session
+        # Vector sync status fragment (htmx polling)
+        Route(
+            "/vector-sync/status",
+            vector_sync_status_fragment,
+            methods=["GET"],
+        ),  # /app/vector-sync/status
+        # Webhook management routes (admin-only)
+        Route("/webhooks", webhook_management_pane, methods=["GET"]),  # /app/webhooks
+        Route(
+            "/webhooks/enable/{preset_id:str}", enable_webhook_preset, methods=["POST"]
+        ),
+        Route(
+            "/webhooks/disable/{preset_id:str}",
+            disable_webhook_preset,
+            methods=["DELETE"],
+        ),
    ]

    browser_app = Starlette(routes=browser_routes)
@@ -1367,9 +1512,14 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
        backend=SessionAuthBackend(oauth_enabled=oauth_enabled),
    )

-    # Mount browser app at /user (so /user and /user/page work)
-    routes.append(Mount("/user", app=browser_app))
-    logger.info("User info routes with session auth: /user, /user/page")
+    # Add redirect from /app to /app/ (Starlette requires trailing slash for mounted apps)
+    routes.append(
+        Route("/app", lambda request: RedirectResponse("/app/", status_code=307))
+    )
+
+    # Mount browser app at /app (webapp and admin routes)
+    routes.append(Mount("/app", app=browser_app))
+    logger.info("App routes with session auth: /app, /app/webhooks, /app/revoke")

    # Mount FastMCP at root last (catch-all, handles OAuth via token_verifier)
    routes.append(Mount("/", app=mcp_app))
@@ -1391,9 +1541,12 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
                )
                logger.info(f"🔑 /mcp request with Authorization: {token_preview}")
            else:
-                logger.warning(
-                    f"⚠️  /mcp request WITHOUT Authorization header from {request.client}"
-                )
+                # Only warn about missing Authorization in OAuth mode
+                # In BasicAuth mode, /mcp requests without Authorization are expected
+                if oauth_enabled:
+                    logger.warning(
+                        f"⚠️  /mcp request WITHOUT Authorization header from {request.client}"
+                    )

            # Log client capabilities on initialize request
            if request.method == "POST":
@@ -1454,7 +1607,7 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
    )

    # Add observability middleware (metrics + tracing)
-    if settings.metrics_enabled or settings.tracing_enabled:
+    if settings.metrics_enabled or settings.otel_exporter_otlp_endpoint:
        app.add_middleware(ObservabilityMiddleware)
        logger.info("Observability middleware enabled (metrics and/or tracing)")

@@ -1487,249 +1640,3 @@ def get_app(transport: str = "sse", enabled_apps: list[str] | None = None):
        logger.info("WWW-Authenticate scope challenge handler enabled")

    return app
-
-
-@click.command()
-@click.option(
-    "--host", "-h", default="127.0.0.1", show_default=True, help="Server host"
-)
-@click.option(
-    "--port", "-p", type=int, default=8000, show_default=True, help="Server port"
-)
-@click.option(
-    "--log-level",
-    "-l",
-    default="info",
-    show_default=True,
-    type=click.Choice(["critical", "error", "warning", "info", "debug", "trace"]),
-    help="Logging level",
-)
-@click.option(
-    "--transport",
-    "-t",
-    default="sse",
-    show_default=True,
-    type=click.Choice(["sse", "streamable-http", "http"]),
-    help="MCP transport protocol",
-)
-@click.option(
-    "--enable-app",
-    "-e",
-    multiple=True,
-    type=click.Choice(
-        ["notes", "tables", "webdav", "calendar", "contacts", "cookbook", "deck"]
-    ),
-    help="Enable specific Nextcloud app APIs. Can be specified multiple times. If not specified, all apps are enabled.",
-)
-@click.option(
-    "--oauth/--no-oauth",
-    default=None,
-    help="Force OAuth mode (if enabled) or BasicAuth mode (if disabled). By default, auto-detected based on environment variables.",
-)
-@click.option(
-    "--oauth-client-id",
-    envvar="NEXTCLOUD_OIDC_CLIENT_ID",
-    help="OAuth client ID (can also use NEXTCLOUD_OIDC_CLIENT_ID env var)",
-)
-@click.option(
-    "--oauth-client-secret",
-    envvar="NEXTCLOUD_OIDC_CLIENT_SECRET",
-    help="OAuth client secret (can also use NEXTCLOUD_OIDC_CLIENT_SECRET env var)",
-)
-@click.option(
-    "--mcp-server-url",
-    envvar="NEXTCLOUD_MCP_SERVER_URL",
-    default="http://localhost:8000",
-    show_default=True,
-    help="MCP server URL for OAuth callbacks (can also use NEXTCLOUD_MCP_SERVER_URL env var)",
-)
-@click.option(
-    "--nextcloud-host",
-    envvar="NEXTCLOUD_HOST",
-    help="Nextcloud instance URL (can also use NEXTCLOUD_HOST env var)",
-)
-@click.option(
-    "--nextcloud-username",
-    envvar="NEXTCLOUD_USERNAME",
-    help="Nextcloud username for BasicAuth (can also use NEXTCLOUD_USERNAME env var)",
-)
-@click.option(
-    "--nextcloud-password",
-    envvar="NEXTCLOUD_PASSWORD",
-    help="Nextcloud password for BasicAuth (can also use NEXTCLOUD_PASSWORD env var)",
-)
-@click.option(
-    "--oauth-scopes",
-    envvar="NEXTCLOUD_OIDC_SCOPES",
-    default="openid profile email notes:read notes:write calendar:read calendar:write todo:read todo:write contacts:read contacts:write cookbook:read cookbook:write deck:read deck:write tables:read tables:write files:read files:write sharing:read sharing:write",
-    show_default=True,
-    help="OAuth scopes to request during client registration. These define the maximum allowed scopes for the client. Note: Actual supported scopes are discovered dynamically from MCP tools at runtime. (can also use NEXTCLOUD_OIDC_SCOPES env var)",
-)
-@click.option(
-    "--oauth-token-type",
-    envvar="NEXTCLOUD_OIDC_TOKEN_TYPE",
-    default="bearer",
-    show_default=True,
-    type=click.Choice(["bearer", "jwt"], case_sensitive=False),
-    help="OAuth token type (can also use NEXTCLOUD_OIDC_TOKEN_TYPE env var)",
-)
-@click.option(
-    "--public-issuer-url",
-    envvar="NEXTCLOUD_PUBLIC_ISSUER_URL",
-    help="Public issuer URL for OAuth (can also use NEXTCLOUD_PUBLIC_ISSUER_URL env var)",
-)
-def run(
-    host: str,
-    port: int,
-    log_level: str,
-    transport: str,
-    enable_app: tuple[str, ...],
-    oauth: bool | None,
-    oauth_client_id: str | None,
-    oauth_client_secret: str | None,
-    mcp_server_url: str,
-    nextcloud_host: str | None,
-    nextcloud_username: str | None,
-    nextcloud_password: str | None,
-    oauth_scopes: str,
-    oauth_token_type: str,
-    public_issuer_url: str | None,
-):
-    """
-    Run the Nextcloud MCP server.
-
-    \b
-    Authentication Modes:
-      - BasicAuth: Set NEXTCLOUD_USERNAME and NEXTCLOUD_PASSWORD
-      - OAuth: Leave USERNAME/PASSWORD unset (requires OIDC app enabled)
-
-    \b
-    Examples:
-      # BasicAuth mode with CLI options
-      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com \\
-          --nextcloud-username=admin --nextcloud-password=secret
-
-      # BasicAuth mode with env vars (recommended for credentials)
-      $ export NEXTCLOUD_HOST=https://cloud.example.com
-      $ export NEXTCLOUD_USERNAME=admin
-      $ export NEXTCLOUD_PASSWORD=secret
-      $ nextcloud-mcp-server --host 0.0.0.0 --port 8000
-
-      # OAuth mode with auto-registration
-      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com --oauth
-
-      # OAuth mode with pre-configured client
-      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com --oauth \\
-          --oauth-client-id=xxx --oauth-client-secret=yyy
-
-      # OAuth mode with custom scopes and JWT tokens
-      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com --oauth \\
-          --oauth-scopes="openid notes:read notes:write" --oauth-token-type=jwt
-
-      # OAuth with public issuer URL (for Docker/proxy setups)
-      $ nextcloud-mcp-server --nextcloud-host=http://app --oauth \\
-          --public-issuer-url=http://localhost:8080
-    """
-    # Set env vars from CLI options if provided
-    if nextcloud_host:
-        os.environ["NEXTCLOUD_HOST"] = nextcloud_host
-    if nextcloud_username:
-        os.environ["NEXTCLOUD_USERNAME"] = nextcloud_username
-    if nextcloud_password:
-        os.environ["NEXTCLOUD_PASSWORD"] = nextcloud_password
-    if oauth_client_id:
-        os.environ["NEXTCLOUD_OIDC_CLIENT_ID"] = oauth_client_id
-    if oauth_client_secret:
-        os.environ["NEXTCLOUD_OIDC_CLIENT_SECRET"] = oauth_client_secret
-    if oauth_scopes:
-        os.environ["NEXTCLOUD_OIDC_SCOPES"] = oauth_scopes
-    if oauth_token_type:
-        os.environ["NEXTCLOUD_OIDC_TOKEN_TYPE"] = oauth_token_type
-    if mcp_server_url:
-        os.environ["NEXTCLOUD_MCP_SERVER_URL"] = mcp_server_url
-    if public_issuer_url:
-        os.environ["NEXTCLOUD_PUBLIC_ISSUER_URL"] = public_issuer_url
-
-    # Force OAuth mode if explicitly requested
-    if oauth is True:
-        # Clear username/password to force OAuth mode
-        if "NEXTCLOUD_USERNAME" in os.environ:
-            click.echo(
-                "Warning: --oauth flag set, ignoring NEXTCLOUD_USERNAME", err=True
-            )
-            del os.environ["NEXTCLOUD_USERNAME"]
-        if "NEXTCLOUD_PASSWORD" in os.environ:
-            click.echo(
-                "Warning: --oauth flag set, ignoring NEXTCLOUD_PASSWORD", err=True
-            )
-            del os.environ["NEXTCLOUD_PASSWORD"]
-
-        # Validate OAuth configuration
-        nextcloud_host = os.getenv("NEXTCLOUD_HOST")
-        if not nextcloud_host:
-            raise click.ClickException(
-                "OAuth mode requires NEXTCLOUD_HOST environment variable to be set"
-            )
-
-        # Check if we have client credentials OR if dynamic registration is possible
-        has_client_creds = os.getenv("NEXTCLOUD_OIDC_CLIENT_ID") and os.getenv(
-            "NEXTCLOUD_OIDC_CLIENT_SECRET"
-        )
-
-        if not has_client_creds:
-            # No client credentials - will attempt dynamic registration
-            # Show helpful message before server starts
-            click.echo("", err=True)
-            click.echo("OAuth Configuration:", err=True)
-            click.echo("  Mode: Dynamic Client Registration", err=True)
-            click.echo("  Host: " + nextcloud_host, err=True)
-            click.echo("  Storage: SQLite (TOKEN_STORAGE_DB)", err=True)
-            click.echo("", err=True)
-            click.echo(
-                "Note: Make sure 'Dynamic Client Registration' is enabled", err=True
-            )
-            click.echo("      in your Nextcloud OIDC app settings.", err=True)
-            click.echo("", err=True)
-        else:
-            click.echo("", err=True)
-            click.echo("OAuth Configuration:", err=True)
-            click.echo("  Mode: Pre-configured Client", err=True)
-            click.echo("  Host: " + nextcloud_host, err=True)
-            click.echo(
-                "  Client ID: "
-                + os.getenv("NEXTCLOUD_OIDC_CLIENT_ID", "")[:16]
-                + "...",
-                err=True,
-            )
-            click.echo("", err=True)
-
-    elif oauth is False:
-        # Force BasicAuth mode - verify credentials exist
-        if not os.getenv("NEXTCLOUD_USERNAME") or not os.getenv("NEXTCLOUD_PASSWORD"):
-            raise click.ClickException(
-                "--no-oauth flag set but NEXTCLOUD_USERNAME or NEXTCLOUD_PASSWORD not set"
-            )
-
-    enabled_apps = list(enable_app) if enable_app else None
-
-    app = get_app(transport=transport, enabled_apps=enabled_apps)
-
-    # Get observability settings and create uvicorn logging config
-    settings = get_settings()
-    uvicorn_log_config = get_uvicorn_logging_config(
-        log_format=settings.log_format,
-        log_level=settings.log_level,
-        include_trace_context=settings.log_include_trace_context,
-    )
-
-    uvicorn.run(
-        app=app,
-        host=host,
-        port=port,
-        log_level=log_level,
-        log_config=uvicorn_log_config,
-    )
-
-
-if __name__ == "__main__":
-    run()
@@ -1,7 +1,7 @@
 """Browser-based OAuth login routes for admin UI.

 Separate from MCP OAuth flow - these routes establish browser sessions
-for accessing admin UI endpoints like /user/page.
+for accessing admin UI endpoints like /app.
 """

 import hashlib
@@ -38,8 +38,8 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
    """
    oauth_ctx = request.app.state.oauth_context
    if not oauth_ctx:
-        # BasicAuth mode - no login needed, redirect to user page
-        return RedirectResponse("/user/page", status_code=302)
+        # BasicAuth mode - no login needed, redirect to app
+        return RedirectResponse("/app", status_code=302)

    storage = oauth_ctx["storage"]
    oauth_client = oauth_ctx["oauth_client"]
@@ -71,7 +71,7 @@ async def oauth_login(request: Request) -> RedirectResponse | JSONResponse:
    await storage.store_oauth_session(
        session_id=state,  # Use state as session ID
        client_id="browser-ui",
-        client_redirect_uri="/user/page",
+        client_redirect_uri="/app",
        state=state,
        code_challenge=code_challenge,
        code_challenge_method="S256",
@@ -383,7 +383,7 @@ async def oauth_login_callback(request: Request) -> RedirectResponse | HTMLRespo
            # Continue anyway - profile cache is optional for browser UI

    # Create response and set session cookie
-    response = RedirectResponse("/user/page", status_code=302)
+    response = RedirectResponse("/app", status_code=302)
    response.set_cookie(
        key="mcp_session",
        value=user_id,
@@ -8,7 +8,7 @@ from typing import Any
 import anyio
 import httpx

-from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage

 logger = logging.getLogger(__name__)

@@ -12,6 +12,10 @@ from mcp.server.fastmcp import Context

 from ..client import NextcloudClient
 from ..config import get_settings
+from ..observability.metrics import (
+    oauth_token_cache_hits_total,
+    oauth_token_exchange_total,
+)
 from .token_exchange import exchange_token_for_audience

 logger = logging.getLogger(__name__)
@@ -138,6 +142,7 @@ async def get_session_client_from_context(
                logger.debug(
                    f"Using cached exchanged token (expires in {expiry - time.time():.1f}s)"
                )
+                oauth_token_cache_hits_total.labels(hit="true").inc()
                return NextcloudClient.from_token(
                    base_url=base_url, token=cached_token, username=username
                )
@@ -145,17 +150,24 @@ async def get_session_client_from_context(
                logger.debug("Cached token expired, removing from cache")
                del _exchange_cache[cache_key]

+        oauth_token_cache_hits_total.labels(hit="false").inc()
+
        # Perform RFC 8693 token exchange
        logger.info(f"Exchanging MCP token for Nextcloud API token (user: {username})")

-        # Exchange for Nextcloud resource URI audience
-        exchanged_token, expires_in = await exchange_token_for_audience(
-            subject_token=mcp_token,
-            requested_audience=settings.nextcloud_resource_uri or "nextcloud",
-            requested_scopes=None,  # Nextcloud doesn't support scopes
-        )
+        try:
+            # Exchange for Nextcloud resource URI audience
+            exchanged_token, expires_in = await exchange_token_for_audience(
+                subject_token=mcp_token,
+                requested_audience=settings.nextcloud_resource_uri or "nextcloud",
+                requested_scopes=None,  # Nextcloud doesn't support scopes
+            )
+            oauth_token_exchange_total.labels(status="success").inc()

-        logger.info(f"Token exchange successful. Token expires in {expires_in}s")
+            logger.info(f"Token exchange successful. Token expires in {expires_in}s")
+        except Exception:
+            oauth_token_exchange_total.labels(status="error").inc()
+            raise

        # Cache the exchanged token
        # Use the minimum of exchange TTL and configured cache TTL
@@ -32,7 +32,7 @@ from starlette.requests import Request
 from starlette.responses import JSONResponse, RedirectResponse

 from nextcloud_mcp_server.auth.client_registry import get_client_registry
-from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage

 logger = logging.getLogger(__name__)

@@ -0,0 +1,54 @@
+"""Permission checking utilities for Nextcloud admin operations."""
+
+import logging
+
+from httpx import AsyncClient
+from starlette.requests import Request
+
+from nextcloud_mcp_server.client.users import UsersClient
+
+logger = logging.getLogger(__name__)
+
+
+async def is_nextcloud_admin(request: Request, http_client: AsyncClient) -> bool:
+    """Check if the authenticated user is a Nextcloud administrator.
+
+    This function extracts the username from the session/request context
+    and checks if the user is a member of the "admin" group in Nextcloud.
+
+    Args:
+        request: Starlette request object with authenticated user
+        http_client: Authenticated HTTP client for Nextcloud API calls
+
+    Returns:
+        True if user is admin, False otherwise
+
+    Example:
+        ```python
+        if await is_nextcloud_admin(request, http_client):
+            # Show admin-only features
+            pass
+        ```
+    """
+    try:
+        # Extract username from authenticated session
+        username = request.user.display_name
+        if not username:
+            logger.warning("No username found in authenticated session")
+            return False
+
+        # Query Nextcloud for user's group memberships
+        users_client = UsersClient(http_client, username)
+        user_groups = await users_client.get_user_groups(username)
+
+        # Check if user is in the admin group
+        is_admin = "admin" in user_groups
+        logger.debug(
+            f"Admin check for user '{username}': {is_admin} (groups: {user_groups})"
+        )
+
+        return is_admin
+
+    except Exception as e:
+        logger.error(f"Error checking admin permissions: {e}", exc_info=True)
+        return False
@@ -13,7 +13,7 @@ from mcp.server.fastmcp import Context
 from mcp.shared.exceptions import McpError
 from mcp.types import ErrorData

-from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage

 logger = logging.getLogger(__name__)

@@ -1,23 +1,28 @@
 """
-Refresh Token Storage for ADR-002 Tier 1: Offline Access
+Persistent Storage for MCP Server State

-Manages two separate concerns for OAuth authentication:
+This module provides SQLite-based storage for multiple concerns across both
+BasicAuth and OAuth authentication modes:

-1. **Refresh Tokens** (for background jobs ONLY)
+1. **Refresh Tokens** (OAuth mode only, for background jobs)
   - Securely stores encrypted refresh tokens for offline access
   - Used ONLY by background jobs to obtain access tokens
   - NEVER used within MCP client sessions or browser sessions

-2. **User Profile Cache** (for browser UI display ONLY)
+2. **User Profile Cache** (OAuth mode only, for browser UI display)
   - Caches IdP user profile data for browser-based admin UI
   - Queried ONCE at login, displayed from cache thereafter
   - NOT used for authorization decisions or background jobs

-IMPORTANT: These are separate concerns. Browser sessions read profile cache for
-display purposes. Background jobs use refresh tokens for API access. Never mix
-the two.
+3. **Webhook Registration Tracking** (both modes, for webhook management)
+   - Tracks registered webhook IDs mapped to presets
+   - Enables persistent webhook state across restarts
+   - Avoids redundant Nextcloud API calls for webhook status

-Tokens are encrypted at rest using Fernet symmetric encryption.
+IMPORTANT: The database is initialized in both BasicAuth and OAuth modes.
+Token storage requires TOKEN_ENCRYPTION_KEY, but webhook tracking does not.
+
+Sensitive data (tokens, secrets) is encrypted at rest using Fernet symmetric encryption.
 """

 import json
@@ -30,29 +35,40 @@ from typing import Any, Optional
 import aiosqlite
 from cryptography.fernet import Fernet

+from nextcloud_mcp_server.observability.metrics import record_db_operation
+
 logger = logging.getLogger(__name__)


 class RefreshTokenStorage:
-    """Securely store and manage user refresh tokens and profile cache.
+    """Persistent storage for MCP server state (tokens, webhooks, and future features).

-    This class manages two separate concerns:
-    - Refresh tokens: Encrypted storage for background job access (write-only by OAuth, read-only by background jobs)
-    - User profiles: Plain JSON cache for browser UI display (written at login, read by UI)
+    This class manages multiple concerns across both BasicAuth and OAuth modes:

-    These concerns are architecturally separate and should never be mixed.
+    **OAuth-specific concerns**:
+    - Refresh tokens: Encrypted storage for background job access (requires encryption key)
+    - User profiles: Plain JSON cache for browser UI display
+    - OAuth client credentials: Encrypted client secrets from DCR
+    - OAuth sessions: Temporary session state for progressive consent flow
+
+    **Both modes**:
+    - Webhook registration: Track registered webhooks mapped to presets
+    - Schema versioning: Handle database migrations automatically
+
+    Token-related operations require TOKEN_ENCRYPTION_KEY, but webhook operations do not.
    """

-    def __init__(self, db_path: str, encryption_key: bytes):
+    def __init__(self, db_path: str, encryption_key: bytes | None = None):
        """
-        Initialize refresh token storage.
+        Initialize persistent storage.

        Args:
            db_path: Path to SQLite database file
-            encryption_key: Fernet encryption key (32 bytes, base64-encoded)
+            encryption_key: Optional Fernet encryption key (32 bytes, base64-encoded).
+                          Required for token storage operations, not required for webhook tracking.
        """
        self.db_path = db_path
-        self.cipher = Fernet(encryption_key)
+        self.cipher = Fernet(encryption_key) if encryption_key else None
        self._initialized = False

    @classmethod
@@ -62,41 +78,42 @@ class RefreshTokenStorage:

        Environment variables:
            TOKEN_STORAGE_DB: Path to database file (default: /app/data/tokens.db)
-            TOKEN_ENCRYPTION_KEY: Base64-encoded Fernet key
+            TOKEN_ENCRYPTION_KEY: Optional base64-encoded Fernet key (required for token storage)

        Returns:
            RefreshTokenStorage instance

-        Raises:
-            ValueError: If TOKEN_ENCRYPTION_KEY is not set
+        Note:
+            If TOKEN_ENCRYPTION_KEY is not set, token storage operations will fail,
+            but webhook tracking will still work.
        """
        db_path = os.getenv("TOKEN_STORAGE_DB", "/app/data/tokens.db")
        encryption_key_b64 = os.getenv("TOKEN_ENCRYPTION_KEY")

-        if not encryption_key_b64:
-            raise ValueError(
-                "TOKEN_ENCRYPTION_KEY environment variable is required. "
-                "Generate one with: python -c 'from cryptography.fernet import Fernet; "
-                "print(Fernet.generate_key().decode())'"
+        encryption_key = None
+        if encryption_key_b64:
+            # Fernet expects a base64url-encoded key as bytes, not decoded bytes
+            # The key from Fernet.generate_key() is already base64url-encoded
+            try:
+                # Convert string to bytes if needed
+                if isinstance(encryption_key_b64, str):
+                    encryption_key = encryption_key_b64.encode()
+                else:
+                    encryption_key = encryption_key_b64
+
+                # Validate the key by trying to create a Fernet instance
+                Fernet(encryption_key)
+            except Exception as e:
+                raise ValueError(
+                    f"Invalid TOKEN_ENCRYPTION_KEY: {e}. "
+                    "Must be a valid Fernet key (base64url-encoded 32 bytes)."
+                ) from e
+        else:
+            logger.info(
+                "TOKEN_ENCRYPTION_KEY not set - token storage operations will be unavailable, "
+                "but webhook tracking will still work"
            )

-        # Fernet expects a base64url-encoded key as bytes, not decoded bytes
-        # The key from Fernet.generate_key() is already base64url-encoded
-        try:
-            # Convert string to bytes if needed
-            if isinstance(encryption_key_b64, str):
-                encryption_key = encryption_key_b64.encode()
-            else:
-                encryption_key = encryption_key_b64
-
-            # Validate the key by trying to create a Fernet instance
-            Fernet(encryption_key)
-        except Exception as e:
-            raise ValueError(
-                f"Invalid TOKEN_ENCRYPTION_KEY: {e}. "
-                "Must be a valid Fernet key (base64url-encoded 32 bytes)."
-            ) from e
-
        return cls(db_path=db_path, encryption_key=encryption_key)

    async def initialize(self) -> None:
@@ -204,6 +221,38 @@ class RefreshTokenStorage:
                "ON oauth_sessions(mcp_authorization_code)"
            )

+            # Schema version tracking
+            await db.execute(
+                """
+                CREATE TABLE IF NOT EXISTS schema_version (
+                    version INTEGER PRIMARY KEY,
+                    applied_at REAL NOT NULL
+                )
+                """
+            )
+
+            # Registered webhooks tracking (both BasicAuth and OAuth modes)
+            await db.execute(
+                """
+                CREATE TABLE IF NOT EXISTS registered_webhooks (
+                    id INTEGER PRIMARY KEY AUTOINCREMENT,
+                    webhook_id INTEGER NOT NULL UNIQUE,
+                    preset_id TEXT NOT NULL,
+                    created_at REAL NOT NULL
+                )
+                """
+            )
+
+            # Create indexes for efficient webhook queries
+            await db.execute(
+                "CREATE INDEX IF NOT EXISTS idx_webhooks_preset "
+                "ON registered_webhooks(preset_id)"
+            )
+            await db.execute(
+                "CREATE INDEX IF NOT EXISTS idx_webhooks_created "
+                "ON registered_webhooks(created_at)"
+            )
+
            await db.commit()

        # Set restrictive permissions after creation
@@ -245,35 +294,43 @@ class RefreshTokenStorage:
        # For Flow 2, set provisioned_at timestamp
        provisioned_at = now if flow_type == "flow2" else None

-        async with aiosqlite.connect(self.db_path) as db:
-            await db.execute(
-                """
-                INSERT OR REPLACE INTO refresh_tokens
-                (user_id, encrypted_token, expires_at, created_at, updated_at,
-                 flow_type, token_audience, provisioned_at, provisioning_client_id, scopes)
-                VALUES (?, ?, ?, COALESCE((SELECT created_at FROM refresh_tokens WHERE user_id = ?), ?), ?,
-                        ?, ?, ?, ?, ?)
-                """,
-                (
-                    user_id,
-                    encrypted_token,
-                    expires_at,
-                    user_id,
-                    now,
-                    now,
-                    flow_type,
-                    token_audience,
-                    provisioned_at,
-                    provisioning_client_id,
-                    scopes_json,
-                ),
-            )
-            await db.commit()
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                await db.execute(
+                    """
+                    INSERT OR REPLACE INTO refresh_tokens
+                    (user_id, encrypted_token, expires_at, created_at, updated_at,
+                     flow_type, token_audience, provisioned_at, provisioning_client_id, scopes)
+                    VALUES (?, ?, ?, COALESCE((SELECT created_at FROM refresh_tokens WHERE user_id = ?), ?), ?,
+                            ?, ?, ?, ?, ?)
+                    """,
+                    (
+                        user_id,
+                        encrypted_token,
+                        expires_at,
+                        user_id,
+                        now,
+                        now,
+                        flow_type,
+                        token_audience,
+                        provisioned_at,
+                        provisioning_client_id,
+                        scopes_json,
+                    ),
+                )
+                await db.commit()
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "insert", duration, "success")

-        logger.info(
-            f"Stored refresh token for user {user_id}"
-            + (f" (expires at {expires_at})" if expires_at else "")
-        )
+            logger.info(
+                f"Stored refresh token for user {user_id}"
+                + (f" (expires at {expires_at})" if expires_at else "")
+            )
+        except Exception:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "insert", duration, "error")
+            raise

        # Audit log
        await self._audit_log(
@@ -375,40 +432,45 @@ class RefreshTokenStorage:
        if not self._initialized:
            await self.initialize()

-        async with aiosqlite.connect(self.db_path) as db:
-            async with db.execute(
-                """
-                SELECT encrypted_token, expires_at, flow_type, token_audience,
-                       provisioned_at, provisioning_client_id, scopes
-                FROM refresh_tokens WHERE user_id = ?
-                """,
-                (user_id,),
-            ) as cursor:
-                row = await cursor.fetchone()
-
-        if not row:
-            logger.debug(f"No refresh token found for user {user_id}")
-            return None
-
-        (
-            encrypted_token,
-            expires_at,
-            flow_type,
-            token_audience,
-            provisioned_at,
-            provisioning_client_id,
-            scopes_json,
-        ) = row
-
-        # Check expiration
-        if expires_at is not None and expires_at < time.time():
-            logger.warning(
-                f"Refresh token for user {user_id} has expired (expired at {expires_at})"
-            )
-            await self.delete_refresh_token(user_id)
-            return None
-
+        start_time = time.time()
        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                async with db.execute(
+                    """
+                    SELECT encrypted_token, expires_at, flow_type, token_audience,
+                           provisioned_at, provisioning_client_id, scopes
+                    FROM refresh_tokens WHERE user_id = ?
+                    """,
+                    (user_id,),
+                ) as cursor:
+                    row = await cursor.fetchone()
+
+            if not row:
+                logger.debug(f"No refresh token found for user {user_id}")
+                duration = time.time() - start_time
+                record_db_operation("sqlite", "select", duration, "success")
+                return None
+
+            (
+                encrypted_token,
+                expires_at,
+                flow_type,
+                token_audience,
+                provisioned_at,
+                provisioning_client_id,
+                scopes_json,
+            ) = row
+
+            # Check expiration
+            if expires_at is not None and expires_at < time.time():
+                logger.warning(
+                    f"Refresh token for user {user_id} has expired (expired at {expires_at})"
+                )
+                await self.delete_refresh_token(user_id)
+                duration = time.time() - start_time
+                record_db_operation("sqlite", "select", duration, "success")
+                return None
+
            decrypted_token = self.cipher.decrypt(encrypted_token).decode()
            scopes = json.loads(scopes_json) if scopes_json else None

@@ -416,6 +478,9 @@ class RefreshTokenStorage:
                f"Retrieved refresh token for user {user_id} (flow_type: {flow_type})"
            )

+            duration = time.time() - start_time
+            record_db_operation("sqlite", "select", duration, "success")
+
            return {
                "refresh_token": decrypted_token,
                "expires_at": expires_at,
@@ -427,6 +492,8 @@ class RefreshTokenStorage:
                "scopes": scopes,
            }
        except Exception as e:
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "select", duration, "error")
            logger.error(f"Failed to decrypt refresh token for user {user_id}: {e}")
            return None

@@ -521,25 +588,34 @@ class RefreshTokenStorage:
        if not self._initialized:
            await self.initialize()

-        async with aiosqlite.connect(self.db_path) as db:
-            cursor = await db.execute(
-                "DELETE FROM refresh_tokens WHERE user_id = ?",
-                (user_id,),
-            )
-            await db.commit()
-            deleted = cursor.rowcount > 0
+        start_time = time.time()
+        try:
+            async with aiosqlite.connect(self.db_path) as db:
+                cursor = await db.execute(
+                    "DELETE FROM refresh_tokens WHERE user_id = ?",
+                    (user_id,),
+                )
+                await db.commit()
+                deleted = cursor.rowcount > 0

-        if deleted:
-            logger.info(f"Deleted refresh token for user {user_id}")
-            await self._audit_log(
-                event="delete_refresh_token",
-                user_id=user_id,
-                auth_method="offline_access",
-            )
-        else:
-            logger.debug(f"No refresh token to delete for user {user_id}")
+            duration = time.time() - start_time
+            record_db_operation("sqlite", "delete", duration, "success")

-        return deleted
+            if deleted:
+                logger.info(f"Deleted refresh token for user {user_id}")
+                await self._audit_log(
+                    event="delete_refresh_token",
+                    user_id=user_id,
+                    auth_method="offline_access",
+                )
+            else:
+                logger.debug(f"No refresh token 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_user_ids(self) -> list[str]:
        """
@@ -1104,6 +1180,123 @@ class RefreshTokenStorage:

        return deleted

+    # ============================================================================
+    # Webhook Registration Tracking (both BasicAuth and OAuth modes)
+    # ============================================================================
+
+    async def store_webhook(self, webhook_id: int, preset_id: str) -> None:
+        """
+        Store registered webhook ID for tracking.
+
+        Args:
+            webhook_id: Nextcloud webhook ID
+            preset_id: Preset identifier (e.g., "notes_sync", "calendar_sync")
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        async with aiosqlite.connect(self.db_path) as db:
+            await db.execute(
+                "INSERT OR REPLACE INTO registered_webhooks (webhook_id, preset_id, created_at) VALUES (?, ?, ?)",
+                (webhook_id, preset_id, time.time()),
+            )
+            await db.commit()
+
+        logger.debug(f"Stored webhook {webhook_id} for preset '{preset_id}'")
+
+    async def get_webhooks_by_preset(self, preset_id: str) -> list[int]:
+        """
+        Get all webhook IDs registered for a preset.
+
+        Args:
+            preset_id: Preset identifier
+
+        Returns:
+            List of webhook IDs
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        async with aiosqlite.connect(self.db_path) as db:
+            cursor = await db.execute(
+                "SELECT webhook_id FROM registered_webhooks WHERE preset_id = ?",
+                (preset_id,),
+            )
+            rows = await cursor.fetchall()
+
+        return [row[0] for row in rows]
+
+    async def delete_webhook(self, webhook_id: int) -> bool:
+        """
+        Remove webhook from tracking.
+
+        Args:
+            webhook_id: Nextcloud webhook ID to remove
+
+        Returns:
+            True if webhook was deleted, False if not found
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        async with aiosqlite.connect(self.db_path) as db:
+            cursor = await db.execute(
+                "DELETE FROM registered_webhooks WHERE webhook_id = ?", (webhook_id,)
+            )
+            await db.commit()
+            deleted = cursor.rowcount > 0
+
+        if deleted:
+            logger.debug(f"Deleted webhook {webhook_id} from tracking")
+
+        return deleted
+
+    async def list_all_webhooks(self) -> list[dict]:
+        """
+        List all tracked webhooks with metadata.
+
+        Returns:
+            List of webhook dictionaries with keys: webhook_id, preset_id, created_at
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        async with aiosqlite.connect(self.db_path) as db:
+            cursor = await db.execute(
+                "SELECT webhook_id, preset_id, created_at FROM registered_webhooks ORDER BY created_at DESC"
+            )
+            rows = await cursor.fetchall()
+
+        return [
+            {"webhook_id": row[0], "preset_id": row[1], "created_at": row[2]}
+            for row in rows
+        ]
+
+    async def clear_preset_webhooks(self, preset_id: str) -> int:
+        """
+        Delete all webhooks for a preset (bulk operation).
+
+        Args:
+            preset_id: Preset identifier
+
+        Returns:
+            Number of webhooks deleted
+        """
+        if not self._initialized:
+            await self.initialize()
+
+        async with aiosqlite.connect(self.db_path) as db:
+            cursor = await db.execute(
+                "DELETE FROM registered_webhooks WHERE preset_id = ?", (preset_id,)
+            )
+            await db.commit()
+            deleted = cursor.rowcount
+
+        if deleted > 0:
+            logger.debug(f"Cleared {deleted} webhook(s) for preset '{preset_id}'")
+
+        return deleted
+

 async def generate_encryption_key() -> str:
    """
@@ -23,7 +23,7 @@ import httpx
 import jwt
 from cryptography.fernet import Fernet

-from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.auth.token_exchange import exchange_token_for_delegation

 logger = logging.getLogger(__name__)
@@ -20,7 +20,7 @@ import httpx
 import jwt

 from ..config import get_settings
-from .refresh_token_storage import RefreshTokenStorage
+from .storage import RefreshTokenStorage

 logger = logging.getLogger(__name__)

@@ -26,6 +26,10 @@ from jwt import PyJWKClient
 from mcp.server.auth.provider import AccessToken, TokenVerifier

 from nextcloud_mcp_server.config import Settings
+from nextcloud_mcp_server.observability.metrics import (
+    oauth_token_cache_hits_total,
+    record_oauth_token_validation,
+)

 logger = logging.getLogger(__name__)

@@ -105,8 +109,11 @@ class UnifiedTokenVerifier(TokenVerifier):
        cached = self._get_cached_token(token)
        if cached:
            logger.debug("Token found in cache")
+            oauth_token_cache_hits_total.labels(hit="true").inc()
            return cached

+        oauth_token_cache_hits_total.labels(hit="false").inc()
+
        # Both modes do the same validation (MCP audience only)
        return await self._verify_mcp_audience(token)

@@ -124,13 +131,24 @@ class UnifiedTokenVerifier(TokenVerifier):
        Returns:
            AccessToken if valid with MCP audience, None otherwise
        """
+        validation_method = "unknown"
        try:
            # Attempt JWT verification first
            if self._is_jwt_format(token) and self.jwks_client:
+                validation_method = "jwt"
                payload = await self._verify_jwt_signature(token)
+                if payload:
+                    record_oauth_token_validation("jwt", "valid")
+                else:
+                    record_oauth_token_validation("jwt", "invalid")
            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")
                if not payload:
                    return None

@@ -146,6 +164,8 @@ class UnifiedTokenVerifier(TokenVerifier):
                    f"Got {audiences}, need MCP ({self.settings.oidc_client_id} or "
                    f"{self.settings.nextcloud_mcp_server_url})"
                )
+                # Record as invalid due to audience mismatch
+                record_oauth_token_validation(validation_method, "invalid")
                return None

            # Log based on mode for clarity
@@ -163,6 +183,7 @@ class UnifiedTokenVerifier(TokenVerifier):

        except Exception as e:
            logger.error(f"Token verification failed: {e}")
+            record_oauth_token_validation(validation_method, "error")
            return None

    def _has_mcp_audience(self, payload: dict[str, Any]) -> bool:
@@ -231,17 +252,21 @@ class UnifiedTokenVerifier(TokenVerifier):
                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 hasattr(self.settings, "oidc_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": (
+                        True
+                        if hasattr(self.settings, "oidc_issuer")
+                        and self.settings.oidc_issuer
+                        else False
+                    ),
                    "verify_aud": False,  # We handle audience validation separately
                },
            )
@@ -19,6 +19,57 @@ from starlette.responses import HTMLResponse, JSONResponse
 logger = logging.getLogger(__name__)


+async def _get_authenticated_client_for_userinfo(request: Request) -> httpx.AsyncClient:
+    """Get an authenticated HTTP client for user info page operations.
+
+    Args:
+        request: Starlette request object
+
+    Returns:
+        Authenticated httpx.AsyncClient
+    """
+    oauth_ctx = getattr(request.app.state, "oauth_context", None)
+
+    # BasicAuth mode - use credentials from environment
+    if not oauth_ctx:
+        nextcloud_host = os.getenv("NEXTCLOUD_HOST")
+        username = os.getenv("NEXTCLOUD_USERNAME")
+        password = os.getenv("NEXTCLOUD_PASSWORD")
+
+        if not all([nextcloud_host, username, password]):
+            raise RuntimeError("BasicAuth credentials not configured")
+
+        assert nextcloud_host is not None  # Type narrowing for type checker
+        return httpx.AsyncClient(
+            base_url=nextcloud_host,
+            auth=(username, password),
+            timeout=30.0,
+        )
+
+    # OAuth mode - get token from session
+    storage = oauth_ctx.get("storage")
+    session_id = request.cookies.get("mcp_session")
+
+    if not storage or not session_id:
+        raise RuntimeError("Session not found")
+
+    token_data = await storage.get_refresh_token(session_id)
+    if not token_data or "access_token" not in token_data:
+        raise RuntimeError("No access token found in session")
+
+    access_token = token_data["access_token"]
+    nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+    if not nextcloud_host:
+        raise RuntimeError("Nextcloud host not configured")
+
+    return httpx.AsyncClient(
+        base_url=nextcloud_host,
+        headers={"Authorization": f"Bearer {access_token}"},
+        timeout=30.0,
+    )
+
+
 async def _get_processing_status(request: Request) -> dict[str, Any] | None:
    """Get vector sync processing status.

@@ -88,6 +139,71 @@ async def _get_processing_status(request: Request) -> dict[str, Any] | None:
        return None


+@requires("authenticated", redirect="oauth_login")
+async def vector_sync_status_fragment(request: Request) -> HTMLResponse:
+    """Vector sync status fragment endpoint - returns HTML fragment with current status.
+
+    This endpoint is polled by htmx to provide real-time updates of vector sync processing
+    status without requiring a full page refresh.
+
+    Requires authentication via session cookie (redirects to oauth_login route if not authenticated).
+
+    Args:
+        request: Starlette request object
+
+    Returns:
+        HTML response with vector sync status table fragment
+    """
+    processing_status = await _get_processing_status(request)
+
+    # If vector sync is disabled or unavailable, return empty fragment
+    if not processing_status:
+        return HTMLResponse(
+            """
+            <div id="vector-sync-status" hx-get="/app/vector-sync/status" hx-trigger="every 10s" hx-swap="innerHTML">
+                <p style="color: #999;">Vector sync not available</p>
+            </div>
+            """
+        )
+
+    indexed_count = processing_status["indexed_count"]
+    pending_count = processing_status["pending_count"]
+    status = processing_status["status"]
+
+    # Format numbers with commas for readability
+    indexed_count_str = f"{indexed_count:,}"
+    pending_count_str = f"{pending_count:,}"
+
+    # Status badge color and text
+    if status == "syncing":
+        status_badge = (
+            '<span style="color: #ff9800; font-weight: bold;">⟳ Syncing</span>'
+        )
+    else:
+        status_badge = '<span style="color: #4caf50; font-weight: bold;">✓ Idle</span>'
+
+    # Return inner content only (container div is in initial page render)
+    html = f"""
+    <h2>Vector Sync Status</h2>
+    <table>
+        <tr>
+            <td><strong>Indexed Documents</strong></td>
+            <td>{indexed_count_str}</td>
+        </tr>
+        <tr>
+            <td><strong>Pending Documents</strong></td>
+            <td>{pending_count_str}</td>
+        </tr>
+        <tr>
+            <td><strong>Status</strong></td>
+            <td>{status_badge}</td>
+        </tr>
+    </table>
+    """
+
+    return HTMLResponse(html)
+
+
 async def _get_userinfo_endpoint(oauth_ctx: dict[str, Any]) -> str | None:
    """Get the correct userinfo endpoint based on OAuth mode.

@@ -296,6 +412,19 @@ async def user_info_html(request: Request) -> HTMLResponse:
    # Get vector sync processing status
    processing_status = await _get_processing_status(request)

+    # Check if user is admin (for Webhooks tab)
+    is_admin = False
+    try:
+        from nextcloud_mcp_server.auth.permissions import is_nextcloud_admin
+
+        # Get authenticated HTTP client
+        http_client = await _get_authenticated_client_for_userinfo(request)
+        is_admin = await is_nextcloud_admin(request, http_client)
+        await http_client.aclose()
+    except Exception as e:
+        logger.warning(f"Failed to check admin status: {e}")
+        # Default to not admin if check fails
+
    # Check for error
    if "error" in user_context and user_context["error"] != "":
        # Get login URL dynamically
@@ -443,43 +572,15 @@ async def user_info_html(request: Request) -> HTMLResponse:
            </div>
            """

-    # Build vector sync status HTML
+    # Build vector sync status HTML (with htmx auto-refresh)
    vector_status_html = ""
    if processing_status:
-        indexed_count = processing_status["indexed_count"]
-        pending_count = processing_status["pending_count"]
-        status = processing_status["status"]
-
-        # Format numbers with commas for readability
-        indexed_count_str = f"{indexed_count:,}"
-        pending_count_str = f"{pending_count:,}"
-
-        # Status badge color and text
-        if status == "syncing":
-            status_badge = (
-                '<span style="color: #ff9800; font-weight: bold;">⟳ Syncing</span>'
-            )
-        else:
-            status_badge = (
-                '<span style="color: #4caf50; font-weight: bold;">✓ Idle</span>'
-            )
-
-        vector_status_html = f"""
-        <h2>Vector Sync Status</h2>
-        <table>
-            <tr>
-                <td><strong>Indexed Documents</strong></td>
-                <td>{indexed_count_str}</td>
-            </tr>
-            <tr>
-                <td><strong>Pending Documents</strong></td>
-                <td>{pending_count_str}</td>
-            </tr>
-            <tr>
-                <td><strong>Status</strong></td>
-                <td>{status_badge}</td>
-            </tr>
-        </table>
+        # Use htmx to load and auto-refresh the status fragment
+        # Container div stays stable, only inner content updates every 10s
+        vector_status_html = """
+            <div id="vector-sync-status" hx-get="/app/vector-sync/status" hx-trigger="load, every 10s" hx-swap="innerHTML">
+                <p style="color: #999;">Loading vector sync status...</p>
+            </div>
        """

    # Build IdP profile HTML
@@ -506,17 +607,61 @@ async def user_info_html(request: Request) -> HTMLResponse:
        <div class="warning">{user_context["idp_profile_error"]}</div>
        """

+    # Build user info tab content
+    user_info_tab_html = f"""
+        <h2>Authentication</h2>
+        <table>
+            <tr>
+                <td><strong>Username</strong></td>
+                <td>{username}</td>
+            </tr>
+            <tr>
+                <td><strong>Authentication Mode</strong></td>
+                <td><span class="badge badge-{auth_mode}">{auth_mode}</span></td>
+            </tr>
+        </table>
+
+        {host_info_html}
+        {session_info_html}
+        {idp_profile_html}
+    """
+
+    # Determine which tabs to show
+    show_vector_sync_tab = processing_status is not None
+    show_webhooks_tab = is_admin
+
+    # Build vector sync tab content (only if enabled)
+    vector_sync_tab_html = ""
+    if show_vector_sync_tab:
+        vector_sync_tab_html = vector_status_html
+
+    # Build webhooks tab content (only if admin)
+    webhooks_tab_html = ""
+    if show_webhooks_tab:
+        webhooks_tab_html = """
+            <div hx-get="/app/webhooks" hx-trigger="load" hx-swap="outerHTML">
+                <p style="color: #999;">Loading webhook management...</p>
+            </div>
+        """
+
    html_content = f"""
    <!DOCTYPE html>
    <html lang="en">
    <head>
        <meta charset="UTF-8">
        <meta name="viewport" content="width=device-width, initial-scale=1.0">
-        <title>User Info - Nextcloud MCP Server</title>
+        <title>Nextcloud MCP Server</title>
+
+        <!-- htmx for dynamic loading -->
+        <script src="https://unpkg.com/htmx.org@1.9.10"></script>
+
+        <!-- Alpine.js for tab state management -->
+        <script defer src="https://cdn.jsdelivr.net/npm/alpinejs@3.x.x/dist/cdn.min.js"></script>
+
        <style>
            body {{
                font-family: -apple-system, BlinkMacSystemFont, "Segoe UI", Roboto, "Helvetica Neue", Arial, sans-serif;
-                max-width: 800px;
+                max-width: 900px;
                margin: 50px auto;
                padding: 20px;
                background-color: #f5f5f5;
@@ -526,6 +671,7 @@ async def user_info_html(request: Request) -> HTMLResponse:
                border-radius: 8px;
                padding: 30px;
                box-shadow: 0 2px 4px rgba(0,0,0,0.1);
+                min-height: calc(100vh - 200px);
            }}
            h1 {{
                color: #0082c9;
@@ -535,10 +681,51 @@ async def user_info_html(request: Request) -> HTMLResponse:
            }}
            h2 {{
                color: #333;
-                margin-top: 30px;
+                margin-top: 20px;
                border-bottom: 1px solid #e0e0e0;
                padding-bottom: 5px;
            }}
+
+            /* Tab navigation */
+            .tabs {{
+                display: flex;
+                gap: 0;
+                margin: 20px 0 0 0;
+                border-bottom: 2px solid #e0e0e0;
+            }}
+            .tab {{
+                padding: 12px 24px;
+                cursor: pointer;
+                background: transparent;
+                border: none;
+                font-size: 14px;
+                font-weight: 500;
+                color: #666;
+                border-bottom: 2px solid transparent;
+                margin-bottom: -2px;
+                transition: all 0.2s;
+            }}
+            .tab:hover {{
+                color: #0082c9;
+                background-color: #f5f5f5;
+            }}
+            .tab.active {{
+                color: #0082c9;
+                border-bottom-color: #0082c9;
+            }}
+
+            /* Tab content - use grid to overlay panes */
+            .tab-content {{
+                padding: 20px 0;
+                display: grid;
+            }}
+
+            /* Tab panes - all occupy the same grid cell to overlay */
+            .tab-pane {{
+                grid-area: 1 / 1;
+            }}
+
+            /* Tables */
            table {{
                width: 100%;
                border-collapse: collapse;
@@ -558,6 +745,8 @@ async def user_info_html(request: Request) -> HTMLResponse:
                border-radius: 3px;
                font-family: 'Courier New', monospace;
            }}
+
+            /* Badges */
            .badge {{
                display: inline-block;
                padding: 3px 8px;
@@ -574,6 +763,8 @@ async def user_info_html(request: Request) -> HTMLResponse:
                background-color: #2196f3;
                color: white;
            }}
+
+            /* Messages */
            .warning {{
                background-color: #fff3cd;
                border-left: 4px solid #ffc107;
@@ -581,11 +772,15 @@ async def user_info_html(request: Request) -> HTMLResponse:
                margin: 15px 0;
                color: #856404;
            }}
-            .logout {{
-                margin-top: 30px;
-                padding-top: 20px;
-                border-top: 1px solid #e0e0e0;
+            .info-message {{
+                background-color: #e3f2fd;
+                border-left: 4px solid #2196f3;
+                padding: 15px;
+                margin: 15px 0;
+                color: #1565c0;
            }}
+
+            /* Buttons */
            .button {{
                display: inline-block;
                padding: 10px 20px;
@@ -594,34 +789,113 @@ async def user_info_html(request: Request) -> HTMLResponse:
                text-decoration: none;
                border-radius: 4px;
                transition: background-color 0.3s;
+                border: none;
+                cursor: pointer;
+                font-size: 14px;
            }}
            .button:hover {{
                background-color: #b71c1c;
            }}
+            .button-primary {{
+                background-color: #0082c9;
+            }}
+            .button-primary:hover {{
+                background-color: #006ba3;
+            }}
+
+            /* Logout section */
+            .logout {{
+                margin-top: 30px;
+                padding-top: 20px;
+                border-top: 1px solid #e0e0e0;
+            }}
+
+            /* Smooth htmx content swaps */
+            .htmx-swapping {{
+                opacity: 0;
+                transition: opacity 200ms ease-out;
+            }}
+
+            /* Smooth htmx content settling */
+            .htmx-settling {{
+                opacity: 1;
+                transition: opacity 200ms ease-in;
+            }}
        </style>
    </head>
    <body>
-        <div class="container">
-            <h1>Nextcloud MCP Server - User Info</h1>
+        <div class="container" x-data="{{ activeTab: 'user-info' }}">
+            <h1>Nextcloud MCP Server</h1>

-            <h2>Authentication</h2>
-            <table>
-                <tr>
-                    <td><strong>Username</strong></td>
-                    <td>{username}</td>
-                </tr>
-                <tr>
-                    <td><strong>Authentication Mode</strong></td>
-                    <td><span class="badge badge-{auth_mode}">{auth_mode}</span></td>
-                </tr>
-            </table>
+            <!-- Tab Navigation -->
+            <div class="tabs">
+                <button
+                    class="tab"
+                    :class="activeTab === 'user-info' ? 'active' : ''"
+                    @click="activeTab = 'user-info'">
+                    User Info
+                </button>
+                {
+        ""
+        if not show_vector_sync_tab
+        else '''
+                <button
+                    class="tab"
+                    :class="activeTab === 'vector-sync' ? 'active' : ''"
+                    @click="activeTab = 'vector-sync'">
+                    Vector Sync
+                </button>
+                '''
+    }
+                {
+        ""
+        if not show_webhooks_tab
+        else '''
+                <button
+                    class="tab"
+                    :class="activeTab === 'webhooks' ? 'active' : ''"
+                    @click="activeTab = 'webhooks'">
+                    Webhooks
+                </button>
+                '''
+    }
+            </div>

-            {host_info_html}
-            {session_info_html}
-            {vector_status_html}
-            {idp_profile_html}
+            <!-- Tab Content -->
+            <div class="tab-content">
+                <!-- User Info Tab -->
+                <div class="tab-pane" x-show="activeTab === 'user-info'" x-transition.opacity.duration.150ms>
+                    {user_info_tab_html}
+                </div>

-            {f'<div class="logout"><a href="{logout_url}" class="button">Logout</a></div>' if auth_mode == "oauth" else ""}
+                {
+        ""
+        if not show_vector_sync_tab
+        else f'''
+                <!-- Vector Sync Tab -->
+                <div class="tab-pane" x-show="activeTab === 'vector-sync'" x-transition.opacity.duration.150ms>
+                    {vector_sync_tab_html}
+                </div>
+                '''
+    }
+
+                {
+        ""
+        if not show_webhooks_tab
+        else f'''
+                <!-- Webhooks Tab (admin-only, loaded dynamically) -->
+                <div class="tab-pane" x-show="activeTab === 'webhooks'" x-transition.opacity.duration.150ms>
+                    {webhooks_tab_html}
+                </div>
+                '''
+    }
+            </div>
+
+            {
+        f'<div class="logout"><a href="{logout_url}" class="button">Logout</a></div>'
+        if auth_mode == "oauth"
+        else ""
+    }
        </div>
    </body>
    </html>
@@ -0,0 +1,540 @@
+"""Webhook management routes for admin UI.
+
+Provides browser-based endpoints for admin users to manage webhook configurations
+using preset templates. Only accessible to Nextcloud administrators.
+"""
+
+import logging
+import os
+
+import httpx
+from starlette.authentication import requires
+from starlette.requests import Request
+from starlette.responses import HTMLResponse
+
+from nextcloud_mcp_server.auth.permissions import is_nextcloud_admin
+from nextcloud_mcp_server.client.webhooks import WebhooksClient
+from nextcloud_mcp_server.server.webhook_presets import (
+    WEBHOOK_PRESETS,
+    filter_presets_by_installed_apps,
+    get_preset,
+)
+
+logger = logging.getLogger(__name__)
+
+
+def _get_storage(request: Request):
+    """Get storage instance from app state.
+
+    Args:
+        request: Starlette request object
+
+    Returns:
+        RefreshTokenStorage instance or None
+    """
+    # Try browser_app state first (for /app routes)
+    storage = getattr(request.app.state, "storage", None)
+
+    # Try oauth_context if in OAuth mode
+    if not storage:
+        oauth_ctx = getattr(request.app.state, "oauth_context", None)
+        if oauth_ctx:
+            storage = oauth_ctx.get("storage")
+
+    return storage
+
+
+async def _get_installed_apps(http_client: httpx.AsyncClient) -> list[str]:
+    """Get list of installed and enabled apps from Nextcloud capabilities.
+
+    Args:
+        http_client: Authenticated HTTP client
+
+    Returns:
+        List of installed app names (e.g., ["notes", "calendar", "forms"])
+    """
+    try:
+        response = await http_client.get(
+            "/ocs/v2.php/cloud/capabilities",
+            headers={"OCS-APIRequest": "true", "Accept": "application/json"},
+        )
+        response.raise_for_status()
+        data = response.json()
+
+        # Extract app names from capabilities
+        capabilities = data.get("ocs", {}).get("data", {}).get("capabilities", {})
+        # Filter out core NC capabilities (not apps)
+        core_keys = {"version", "core"}
+        app_keys = set(capabilities.keys()) - core_keys
+        return sorted(app_keys)
+    except Exception as e:
+        logger.warning(f"Failed to get installed apps from capabilities: {e}")
+        return []
+
+
+def _get_webhook_uri() -> str:
+    """Get the webhook endpoint URI for this MCP server.
+
+    This function determines the correct webhook URL based on the environment:
+    1. Uses WEBHOOK_INTERNAL_URL if explicitly set (highest priority)
+    2. Detects Docker environment and uses internal service name
+    3. Falls back to NEXTCLOUD_MCP_SERVER_URL
+
+    In Docker environments, Nextcloud needs to reach the MCP service using
+    the internal Docker network hostname (e.g., http://mcp:8000), not localhost.
+
+    Returns:
+        Full webhook endpoint URL accessible from Nextcloud
+    """
+    # Explicit override (highest priority)
+    webhook_url = os.getenv("WEBHOOK_INTERNAL_URL")
+    if webhook_url:
+        return f"{webhook_url}/webhooks/nextcloud"
+
+    # Detect Docker environment
+    # Check for common Docker indicators
+    is_docker = (
+        os.path.exists("/.dockerenv")  # Docker container marker file
+        or os.path.exists("/run/.containerenv")  # Podman marker
+        or os.getenv("DOCKER_CONTAINER") == "true"  # Explicit flag
+    )
+
+    if is_docker:
+        # In Docker, use internal service name from NEXTCLOUD_MCP_SERVICE_NAME
+        # or default to 'mcp' (docker-compose service name)
+        service_name = os.getenv("NEXTCLOUD_MCP_SERVICE_NAME", "mcp")
+        port = os.getenv("NEXTCLOUD_MCP_PORT", "8000")
+        logger.debug(
+            f"Docker environment detected, using internal URL: http://{service_name}:{port}"
+        )
+        return f"http://{service_name}:{port}/webhooks/nextcloud"
+
+    # Fallback to configured server URL (for non-Docker deployments)
+    server_url = os.getenv("NEXTCLOUD_MCP_SERVER_URL", "http://localhost:8000")
+    return f"{server_url}/webhooks/nextcloud"
+
+
+async def _get_authenticated_client(request: Request) -> httpx.AsyncClient:
+    """Get an authenticated HTTP client for Nextcloud API calls.
+
+    Args:
+        request: Starlette request object
+
+    Returns:
+        Authenticated httpx.AsyncClient
+
+    Raises:
+        RuntimeError: If unable to create authenticated client
+    """
+    # Get OAuth context from app state
+    oauth_ctx = getattr(request.app.state, "oauth_context", None)
+
+    # BasicAuth mode - use credentials from environment
+    if not oauth_ctx:
+        nextcloud_host = os.getenv("NEXTCLOUD_HOST")
+        username = os.getenv("NEXTCLOUD_USERNAME")
+        password = os.getenv("NEXTCLOUD_PASSWORD")
+
+        if not all([nextcloud_host, username, password]):
+            raise RuntimeError("BasicAuth credentials not configured")
+
+        assert nextcloud_host is not None  # Type narrowing for type checker
+        return httpx.AsyncClient(
+            base_url=nextcloud_host,
+            auth=(username, password),
+            timeout=30.0,
+        )
+
+    # OAuth mode - get token from session
+    storage = oauth_ctx.get("storage")
+    session_id = request.cookies.get("mcp_session")
+
+    if not storage or not session_id:
+        raise RuntimeError("Session not found")
+
+    token_data = await storage.get_refresh_token(session_id)
+    if not token_data or "access_token" not in token_data:
+        raise RuntimeError("No access token found in session")
+
+    access_token = token_data["access_token"]
+    nextcloud_host = oauth_ctx.get("config", {}).get("nextcloud_host", "")
+
+    if not nextcloud_host:
+        raise RuntimeError("Nextcloud host not configured")
+
+    return httpx.AsyncClient(
+        base_url=nextcloud_host,
+        headers={"Authorization": f"Bearer {access_token}"},
+        timeout=30.0,
+    )
+
+
+async def _get_enabled_presets(
+    webhooks_client: WebhooksClient,
+    storage=None,
+) -> dict[str, list[int]]:
+    """Get currently enabled webhook presets.
+
+    Reads from database first for better performance. Falls back to API if needed.
+
+    Args:
+        webhooks_client: Webhooks API client
+        storage: Optional RefreshTokenStorage instance
+
+    Returns:
+        Dictionary mapping preset_id to list of webhook IDs
+    """
+    try:
+        # Try database first (faster, works offline)
+        if storage:
+            all_webhooks = await storage.list_all_webhooks()
+            enabled_presets: dict[str, list[int]] = {}
+
+            for webhook in all_webhooks:
+                preset_id = webhook["preset_id"]
+                webhook_id = webhook["webhook_id"]
+
+                if preset_id not in enabled_presets:
+                    enabled_presets[preset_id] = []
+                enabled_presets[preset_id].append(webhook_id)
+
+            return enabled_presets
+
+        # Fallback to API query
+        registered_webhooks = await webhooks_client.list_webhooks()
+        webhook_uri = _get_webhook_uri()
+
+        # Group webhooks by preset based on matching events
+        enabled_presets: dict[str, list[int]] = {}
+
+        for preset_id, preset in WEBHOOK_PRESETS.items():
+            preset_event_classes = {event["event"] for event in preset["events"]}
+            matching_webhooks = []
+
+            for webhook in registered_webhooks:
+                # Check if webhook matches this preset
+                if (
+                    webhook.get("uri") == webhook_uri
+                    and webhook.get("event") in preset_event_classes
+                ):
+                    matching_webhooks.append(webhook["id"])
+
+            if matching_webhooks:
+                enabled_presets[preset_id] = matching_webhooks
+
+        return enabled_presets
+
+    except Exception as e:
+        logger.error(f"Failed to list webhooks: {e}")
+        return {}
+
+
+@requires("authenticated", redirect="oauth_login")
+async def webhook_management_pane(request: Request) -> HTMLResponse:
+    """Webhook management pane - returns HTML for webhook configuration.
+
+    This endpoint checks if the user is an admin and returns either:
+    - Admin view: Webhook management interface with preset controls
+    - Non-admin view: Message indicating admin-only access
+
+    Args:
+        request: Starlette request object
+
+    Returns:
+        HTML response with webhook management interface or access denied message
+    """
+    try:
+        # Get authenticated HTTP client
+        http_client = await _get_authenticated_client(request)
+        username = request.user.display_name
+
+        # Check admin permissions
+        is_admin = await is_nextcloud_admin(request, http_client)
+
+        if not is_admin:
+            return HTMLResponse(
+                content="""
+                <div class="info-message">
+                    <p><strong>Admin Access Required</strong></p>
+                    <p>Webhook management is only available to Nextcloud administrators.</p>
+                    <p>Your account does not have admin privileges.</p>
+                </div>
+                """
+            )
+
+        # Get webhooks client
+        webhooks_client = WebhooksClient(http_client, username)
+
+        # Get storage for database-backed webhook tracking
+        storage = _get_storage(request)
+
+        # Get installed apps to filter presets
+        installed_apps = await _get_installed_apps(http_client)
+        logger.debug(f"Installed apps: {installed_apps}")
+
+        # Get currently enabled presets (from database or API)
+        enabled_presets = await _get_enabled_presets(webhooks_client, storage)
+
+        # Filter presets based on installed apps
+        available_presets = filter_presets_by_installed_apps(installed_apps)
+
+        # Build preset cards HTML
+        preset_cards_html = ""
+        for preset_id, preset in available_presets:
+            is_enabled = preset_id in enabled_presets
+            num_webhooks = len(enabled_presets.get(preset_id, []))
+
+            # Status badge
+            if is_enabled:
+                status_badge = f'<span style="color: #4caf50; font-weight: bold;">✓ Enabled ({num_webhooks} webhooks)</span>'
+                action_button = f"""
+                <button
+                    hx-delete="/app/webhooks/disable/{preset_id}"
+                    hx-target="#preset-{preset_id}"
+                    hx-swap="outerHTML"
+                    class="button"
+                    style="background-color: #ff9800;">
+                    Disable
+                </button>
+                """
+            else:
+                status_badge = '<span style="color: #999;">Not Enabled</span>'
+                action_button = f"""
+                <button
+                    hx-post="/app/webhooks/enable/{preset_id}"
+                    hx-target="#preset-{preset_id}"
+                    hx-swap="outerHTML"
+                    class="button button-primary">
+                    Enable
+                </button>
+                """
+
+            preset_cards_html += f"""
+            <div id="preset-{preset_id}" style="border: 1px solid #e0e0e0; border-radius: 6px; padding: 20px; margin: 15px 0;">
+                <h3 style="margin-top: 0; color: #0082c9;">{preset["name"]}</h3>
+                <p style="color: #666; margin: 10px 0;">{preset["description"]}</p>
+                <p style="font-size: 13px; color: #999;">
+                    <strong>App:</strong> {preset["app"]} |
+                    <strong>Events:</strong> {len(preset["events"])}
+                </p>
+                <div style="margin-top: 15px; display: flex; align-items: center; gap: 15px;">
+                    <div>{status_badge}</div>
+                    <div>{action_button}</div>
+                </div>
+            </div>
+            """
+
+        # Get webhook endpoint URL for display
+        webhook_uri = _get_webhook_uri()
+
+        html_content = f"""
+        <h2>Webhook Management</h2>
+        <div class="info-message">
+            <p><strong>About Webhooks</strong></p>
+            <p>Webhooks enable real-time synchronization by notifying this server when content changes in Nextcloud.</p>
+            <p><strong>Endpoint:</strong> <code>{webhook_uri}</code></p>
+        </div>
+
+        <h3 style="margin-top: 30px;">Available Presets</h3>
+        <p style="color: #666;">Enable webhook presets with one click for common synchronization scenarios.</p>
+        <p style="color: #999; font-size: 13px; margin-top: 5px;">Showing {len(available_presets)} preset(s) for your installed apps ({len(installed_apps)} detected)</p>
+
+        {preset_cards_html}
+        """
+
+        return HTMLResponse(content=html_content)
+
+    except Exception as e:
+        logger.error(f"Error loading webhook management pane: {e}", exc_info=True)
+        return HTMLResponse(
+            content=f"""
+            <div class="warning">
+                <p><strong>Error Loading Webhooks</strong></p>
+                <p>{str(e)}</p>
+            </div>
+            """,
+            status_code=500,
+        )
+
+
+@requires("authenticated", redirect="oauth_login")
+async def enable_webhook_preset(request: Request) -> HTMLResponse:
+    """Enable a webhook preset by registering all webhooks.
+
+    Args:
+        request: Starlette request object (preset_id in path)
+
+    Returns:
+        HTML response with updated preset card
+    """
+    preset_id = request.path_params["preset_id"]
+
+    try:
+        # Get authenticated HTTP client
+        http_client = await _get_authenticated_client(request)
+        username = request.user.display_name
+
+        # Check admin permissions
+        is_admin = await is_nextcloud_admin(request, http_client)
+        if not is_admin:
+            return HTMLResponse(
+                content='<div class="warning">Admin access required</div>',
+                status_code=403,
+            )
+
+        # Get preset configuration
+        preset = get_preset(preset_id)
+        if not preset:
+            return HTMLResponse(
+                content=f'<div class="warning">Unknown preset: {preset_id}</div>',
+                status_code=404,
+            )
+
+        # Register webhooks
+        webhooks_client = WebhooksClient(http_client, username)
+        webhook_uri = _get_webhook_uri()
+        registered_ids = []
+
+        for event_config in preset["events"]:
+            webhook_data = await webhooks_client.create_webhook(
+                event=event_config["event"],
+                uri=webhook_uri,
+                event_filter=event_config["filter"] if event_config["filter"] else None,
+            )
+            webhook_id = webhook_data["id"]
+            registered_ids.append(webhook_id)
+            logger.info(f"Registered webhook {webhook_id} for {event_config['event']}")
+
+        # Persist webhook IDs to database
+        storage = _get_storage(request)
+        if storage:
+            for webhook_id in registered_ids:
+                await storage.store_webhook(webhook_id, preset_id)
+            logger.info(
+                f"Persisted {len(registered_ids)} webhook(s) for preset '{preset_id}' to database"
+            )
+
+        # Return updated card
+        num_webhooks = len(registered_ids)
+        return HTMLResponse(
+            content=f"""
+            <div id="preset-{preset_id}" style="border: 1px solid #e0e0e0; border-radius: 6px; padding: 20px; margin: 15px 0;">
+                <h3 style="margin-top: 0; color: #0082c9;">{preset["name"]}</h3>
+                <p style="color: #666; margin: 10px 0;">{preset["description"]}</p>
+                <p style="font-size: 13px; color: #999;">
+                    <strong>App:</strong> {preset["app"]} |
+                    <strong>Events:</strong> {len(preset["events"])}
+                </p>
+                <div style="margin-top: 15px; display: flex; align-items: center; gap: 15px;">
+                    <div><span style="color: #4caf50; font-weight: bold;">✓ Enabled ({num_webhooks} webhooks)</span></div>
+                    <div>
+                        <button
+                            hx-delete="/app/webhooks/disable/{preset_id}"
+                            hx-target="#preset-{preset_id}"
+                            hx-swap="outerHTML"
+                            class="button"
+                            style="background-color: #ff9800;">
+                            Disable
+                        </button>
+                    </div>
+                </div>
+            </div>
+            """
+        )
+
+    except Exception as e:
+        logger.error(f"Failed to enable preset {preset_id}: {e}", exc_info=True)
+        return HTMLResponse(
+            content=f'<div class="warning">Failed to enable preset: {str(e)}</div>',
+            status_code=500,
+        )
+
+
+@requires("authenticated", redirect="oauth_login")
+async def disable_webhook_preset(request: Request) -> HTMLResponse:
+    """Disable a webhook preset by deleting all registered webhooks.
+
+    Args:
+        request: Starlette request object (preset_id in path)
+
+    Returns:
+        HTML response with updated preset card
+    """
+    preset_id = request.path_params["preset_id"]
+
+    try:
+        # Get authenticated HTTP client
+        http_client = await _get_authenticated_client(request)
+        username = request.user.display_name
+
+        # Check admin permissions
+        is_admin = await is_nextcloud_admin(request, http_client)
+        if not is_admin:
+            return HTMLResponse(
+                content='<div class="warning">Admin access required</div>',
+                status_code=403,
+            )
+
+        # Get preset configuration
+        preset = get_preset(preset_id)
+        if not preset:
+            return HTMLResponse(
+                content=f'<div class="warning">Unknown preset: {preset_id}</div>',
+                status_code=404,
+            )
+
+        # Find and delete matching webhooks
+        webhooks_client = WebhooksClient(http_client, username)
+
+        # Get webhook IDs from database first (more reliable)
+        storage = _get_storage(request)
+        if storage:
+            webhook_ids = await storage.get_webhooks_by_preset(preset_id)
+        else:
+            # Fallback to API query if storage not available
+            enabled_presets = await _get_enabled_presets(webhooks_client)
+            webhook_ids = enabled_presets.get(preset_id, [])
+
+        for webhook_id in webhook_ids:
+            await webhooks_client.delete_webhook(webhook_id)
+            logger.info(f"Deleted webhook {webhook_id} from preset {preset_id}")
+
+        # Remove from database
+        if storage:
+            deleted_count = await storage.clear_preset_webhooks(preset_id)
+            logger.info(
+                f"Removed {deleted_count} webhook(s) for preset '{preset_id}' from database"
+            )
+
+        # Return updated card
+        return HTMLResponse(
+            content=f"""
+            <div id="preset-{preset_id}" style="border: 1px solid #e0e0e0; border-radius: 6px; padding: 20px; margin: 15px 0;">
+                <h3 style="margin-top: 0; color: #0082c9;">{preset["name"]}</h3>
+                <p style="color: #666; margin: 10px 0;">{preset["description"]}</p>
+                <p style="font-size: 13px; color: #999;">
+                    <strong>App:</strong> {preset["app"]} |
+                    <strong>Events:</strong> {len(preset["events"])}
+                </p>
+                <div style="margin-top: 15px; display: flex; align-items: center; gap: 15px;">
+                    <div><span style="color: #999;">Not Enabled</span></div>
+                    <div>
+                        <button
+                            hx-post="/app/webhooks/enable/{preset_id}"
+                            hx-target="#preset-{preset_id}"
+                            hx-swap="outerHTML"
+                            class="button button-primary">
+                            Enable
+                        </button>
+                    </div>
+                </div>
+            </div>
+            """
+        )
+
+    except Exception as e:
+        logger.error(f"Failed to disable preset {preset_id}: {e}", exc_info=True)
+        return HTMLResponse(
+            content=f'<div class="warning">Failed to disable preset: {str(e)}</div>',
+            status_code=500,
+        )
@@ -0,0 +1,257 @@
+import os
+
+import click
+import uvicorn
+
+from nextcloud_mcp_server.config import (
+    get_settings,
+)
+from nextcloud_mcp_server.observability import get_uvicorn_logging_config
+
+from .app import get_app
+
+
+@click.command()
+@click.option(
+    "--host", "-h", default="127.0.0.1", show_default=True, help="Server host"
+)
+@click.option(
+    "--port", "-p", type=int, default=8000, show_default=True, help="Server port"
+)
+@click.option(
+    "--log-level",
+    "-l",
+    default="info",
+    show_default=True,
+    type=click.Choice(["critical", "error", "warning", "info", "debug", "trace"]),
+    help="Logging level",
+)
+@click.option(
+    "--transport",
+    "-t",
+    default="sse",
+    show_default=True,
+    type=click.Choice(["sse", "streamable-http", "http"]),
+    help="MCP transport protocol",
+)
+@click.option(
+    "--enable-app",
+    "-e",
+    multiple=True,
+    type=click.Choice(
+        ["notes", "tables", "webdav", "calendar", "contacts", "cookbook", "deck"]
+    ),
+    help="Enable specific Nextcloud app APIs. Can be specified multiple times. If not specified, all apps are enabled.",
+)
+@click.option(
+    "--oauth/--no-oauth",
+    default=None,
+    help="Force OAuth mode (if enabled) or BasicAuth mode (if disabled). By default, auto-detected based on environment variables.",
+)
+@click.option(
+    "--oauth-client-id",
+    envvar="NEXTCLOUD_OIDC_CLIENT_ID",
+    help="OAuth client ID (can also use NEXTCLOUD_OIDC_CLIENT_ID env var)",
+)
+@click.option(
+    "--oauth-client-secret",
+    envvar="NEXTCLOUD_OIDC_CLIENT_SECRET",
+    help="OAuth client secret (can also use NEXTCLOUD_OIDC_CLIENT_SECRET env var)",
+)
+@click.option(
+    "--mcp-server-url",
+    envvar="NEXTCLOUD_MCP_SERVER_URL",
+    default="http://localhost:8000",
+    show_default=True,
+    help="MCP server URL for OAuth callbacks (can also use NEXTCLOUD_MCP_SERVER_URL env var)",
+)
+@click.option(
+    "--nextcloud-host",
+    envvar="NEXTCLOUD_HOST",
+    help="Nextcloud instance URL (can also use NEXTCLOUD_HOST env var)",
+)
+@click.option(
+    "--nextcloud-username",
+    envvar="NEXTCLOUD_USERNAME",
+    help="Nextcloud username for BasicAuth (can also use NEXTCLOUD_USERNAME env var)",
+)
+@click.option(
+    "--nextcloud-password",
+    envvar="NEXTCLOUD_PASSWORD",
+    help="Nextcloud password for BasicAuth (can also use NEXTCLOUD_PASSWORD env var)",
+)
+@click.option(
+    "--oauth-scopes",
+    envvar="NEXTCLOUD_OIDC_SCOPES",
+    default="openid profile email notes:read notes:write calendar:read calendar:write todo:read todo:write contacts:read contacts:write cookbook:read cookbook:write deck:read deck:write tables:read tables:write files:read files:write sharing:read sharing:write",
+    show_default=True,
+    help="OAuth scopes to request during client registration. These define the maximum allowed scopes for the client. Note: Actual supported scopes are discovered dynamically from MCP tools at runtime. (can also use NEXTCLOUD_OIDC_SCOPES env var)",
+)
+@click.option(
+    "--oauth-token-type",
+    envvar="NEXTCLOUD_OIDC_TOKEN_TYPE",
+    default="bearer",
+    show_default=True,
+    type=click.Choice(["bearer", "jwt"], case_sensitive=False),
+    help="OAuth token type (can also use NEXTCLOUD_OIDC_TOKEN_TYPE env var)",
+)
+@click.option(
+    "--public-issuer-url",
+    envvar="NEXTCLOUD_PUBLIC_ISSUER_URL",
+    help="Public issuer URL for OAuth (can also use NEXTCLOUD_PUBLIC_ISSUER_URL env var)",
+)
+def run(
+    host: str,
+    port: int,
+    log_level: str,
+    transport: str,
+    enable_app: tuple[str, ...],
+    oauth: bool | None,
+    oauth_client_id: str | None,
+    oauth_client_secret: str | None,
+    mcp_server_url: str,
+    nextcloud_host: str | None,
+    nextcloud_username: str | None,
+    nextcloud_password: str | None,
+    oauth_scopes: str,
+    oauth_token_type: str,
+    public_issuer_url: str | None,
+):
+    """
+    Run the Nextcloud MCP server.
+
+    \b
+    Authentication Modes:
+      - BasicAuth: Set NEXTCLOUD_USERNAME and NEXTCLOUD_PASSWORD
+      - OAuth: Leave USERNAME/PASSWORD unset (requires OIDC app enabled)
+
+    \b
+    Examples:
+      # BasicAuth mode with CLI options
+      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com \\
+          --nextcloud-username=admin --nextcloud-password=secret
+
+      # BasicAuth mode with env vars (recommended for credentials)
+      $ export NEXTCLOUD_HOST=https://cloud.example.com
+      $ export NEXTCLOUD_USERNAME=admin
+      $ export NEXTCLOUD_PASSWORD=secret
+      $ nextcloud-mcp-server --host 0.0.0.0 --port 8000
+
+      # OAuth mode with auto-registration
+      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com --oauth
+
+      # OAuth mode with pre-configured client
+      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com --oauth \\
+          --oauth-client-id=xxx --oauth-client-secret=yyy
+
+      # OAuth mode with custom scopes and JWT tokens
+      $ nextcloud-mcp-server --nextcloud-host=https://cloud.example.com --oauth \\
+          --oauth-scopes="openid notes:read notes:write" --oauth-token-type=jwt
+
+      # OAuth with public issuer URL (for Docker/proxy setups)
+      $ nextcloud-mcp-server --nextcloud-host=http://app --oauth \\
+          --public-issuer-url=http://localhost:8080
+    """
+    # Set env vars from CLI options if provided
+    if nextcloud_host:
+        os.environ["NEXTCLOUD_HOST"] = nextcloud_host
+    if nextcloud_username:
+        os.environ["NEXTCLOUD_USERNAME"] = nextcloud_username
+    if nextcloud_password:
+        os.environ["NEXTCLOUD_PASSWORD"] = nextcloud_password
+    if oauth_client_id:
+        os.environ["NEXTCLOUD_OIDC_CLIENT_ID"] = oauth_client_id
+    if oauth_client_secret:
+        os.environ["NEXTCLOUD_OIDC_CLIENT_SECRET"] = oauth_client_secret
+    if oauth_scopes:
+        os.environ["NEXTCLOUD_OIDC_SCOPES"] = oauth_scopes
+    if oauth_token_type:
+        os.environ["NEXTCLOUD_OIDC_TOKEN_TYPE"] = oauth_token_type
+    if mcp_server_url:
+        os.environ["NEXTCLOUD_MCP_SERVER_URL"] = mcp_server_url
+    if public_issuer_url:
+        os.environ["NEXTCLOUD_PUBLIC_ISSUER_URL"] = public_issuer_url
+
+    # Force OAuth mode if explicitly requested
+    if oauth is True:
+        # Clear username/password to force OAuth mode
+        if "NEXTCLOUD_USERNAME" in os.environ:
+            click.echo(
+                "Warning: --oauth flag set, ignoring NEXTCLOUD_USERNAME", err=True
+            )
+            del os.environ["NEXTCLOUD_USERNAME"]
+        if "NEXTCLOUD_PASSWORD" in os.environ:
+            click.echo(
+                "Warning: --oauth flag set, ignoring NEXTCLOUD_PASSWORD", err=True
+            )
+            del os.environ["NEXTCLOUD_PASSWORD"]
+
+        # Validate OAuth configuration
+        nextcloud_host = os.getenv("NEXTCLOUD_HOST")
+        if not nextcloud_host:
+            raise click.ClickException(
+                "OAuth mode requires NEXTCLOUD_HOST environment variable to be set"
+            )
+
+        # Check if we have client credentials OR if dynamic registration is possible
+        has_client_creds = os.getenv("NEXTCLOUD_OIDC_CLIENT_ID") and os.getenv(
+            "NEXTCLOUD_OIDC_CLIENT_SECRET"
+        )
+
+        if not has_client_creds:
+            # No client credentials - will attempt dynamic registration
+            # Show helpful message before server starts
+            click.echo("", err=True)
+            click.echo("OAuth Configuration:", err=True)
+            click.echo("  Mode: Dynamic Client Registration", err=True)
+            click.echo("  Host: " + nextcloud_host, err=True)
+            click.echo("  Storage: SQLite (TOKEN_STORAGE_DB)", err=True)
+            click.echo("", err=True)
+            click.echo(
+                "Note: Make sure 'Dynamic Client Registration' is enabled", err=True
+            )
+            click.echo("      in your Nextcloud OIDC app settings.", err=True)
+            click.echo("", err=True)
+        else:
+            click.echo("", err=True)
+            click.echo("OAuth Configuration:", err=True)
+            click.echo("  Mode: Pre-configured Client", err=True)
+            click.echo("  Host: " + nextcloud_host, err=True)
+            click.echo(
+                "  Client ID: "
+                + os.getenv("NEXTCLOUD_OIDC_CLIENT_ID", "")[:16]
+                + "...",
+                err=True,
+            )
+            click.echo("", err=True)
+
+    elif oauth is False:
+        # Force BasicAuth mode - verify credentials exist
+        if not os.getenv("NEXTCLOUD_USERNAME") or not os.getenv("NEXTCLOUD_PASSWORD"):
+            raise click.ClickException(
+                "--no-oauth flag set but NEXTCLOUD_USERNAME or NEXTCLOUD_PASSWORD not set"
+            )
+
+    enabled_apps = list(enable_app) if enable_app else None
+
+    app = get_app(transport=transport, enabled_apps=enabled_apps)
+
+    # Get observability settings and create uvicorn logging config
+    settings = get_settings()
+    uvicorn_log_config = get_uvicorn_logging_config(
+        log_format=settings.log_format,
+        log_level=settings.log_level,
+        include_trace_context=settings.log_include_trace_context,
+    )
+
+    uvicorn.run(
+        app=app,
+        host=host,
+        port=port,
+        log_level=log_level,
+        log_config=uvicorn_log_config,
+    )
+
+
+if __name__ == "__main__":
+    run()
@@ -9,6 +9,7 @@ from httpx import (
    BasicAuth,
    Request,
    Response,
+    Timeout,
 )

 from ..controllers.notes_search import NotesSearchController
@@ -22,6 +23,7 @@ from .sharing import SharingClient
 from .tables import TablesClient
 from .users import UsersClient
 from .webdav import WebDAVClient
+from .webhooks import WebhooksClient

 logger = logging.getLogger(__name__)

@@ -66,6 +68,7 @@ class NextcloudClient:
            auth=auth,
            transport=AsyncDisableCookieTransport(AsyncHTTPTransport()),
            event_hooks={"request": [log_request], "response": [log_response]},
+            timeout=Timeout(timeout=30, connect=5),
        )

        # Initialize app clients
@@ -81,6 +84,7 @@ class NextcloudClient:
        self.users = UsersClient(self._client, username)
        self.groups = GroupsClient(self._client, username)
        self.sharing = SharingClient(self._client, username)
+        self.webhooks = WebhooksClient(self._client, username)

        # Initialize controllers
        self._notes_search = NotesSearchController()
@@ -18,18 +18,57 @@ class NotesClient(BaseNextcloudClient):
        response = await self._make_request("GET", "/apps/notes/api/v1/settings")
        return response.json()

-    async def get_all_notes(self) -> AsyncIterator[Dict[str, Any]]:
-        """Get all notes, yielding them one at a time."""
+    async def get_all_notes(
+        self, prune_before: Optional[int] = None
+    ) -> AsyncIterator[Dict[str, Any]]:
+        """Get all notes, yielding them one at a time.
+
+        The Notes API returns changed notes with full data in chunks, and ALL note IDs
+        (with only 'id' field) in the last chunk for deletion detection. This causes
+        duplicates which we handle by tracking seen IDs (first occurrence with full
+        data is kept, later pruned duplicates are skipped).
+
+        Args:
+            prune_before: Optional Unix timestamp. Notes unchanged since this time
+                         are pruned (only 'id' field returned in last chunk).
+                         Reduces data transfer for large note collections.
+
+        Yields:
+            Note dictionaries with full data (deduplicated).
+        """
        cursor = ""
+        seen_ids: set[int] = set()

        while True:
+            params: Dict[str, Any] = {"chunkSize": 10}
+            if cursor:
+                params["chunkCursor"] = cursor
+            if prune_before is not None:
+                params["pruneBefore"] = prune_before
+
            response = await self._make_request(
                "GET",
                "/apps/notes/api/v1/notes",
-                params={"chunkSize": 10, "chunkCursor": cursor},
+                params=params,
            )
-            for note in response.json():
+            response_data = response.json()
+
+            for note in response_data:
+                note_id = note.get("id")
+                if note_id is None:
+                    logger.warning(f"Skipping note without ID: {note}")
+                    continue
+
+                # Skip duplicates (API returns all IDs in last chunk for deletion detection)
+                if note_id in seen_ids:
+                    logger.debug(
+                        f"Skipping duplicate note {note_id} (pruned version in last chunk)"
+                    )
+                    continue
+
+                seen_ids.add(note_id)
                yield note
+
            if "X-Notes-Chunk-Cursor" not in response.headers:
                break
            cursor = response.headers["X-Notes-Chunk-Cursor"]
@@ -0,0 +1,109 @@
+"""Client for Nextcloud Webhook Listeners API operations."""
+
+from typing import Any, Dict, List, Optional
+
+from nextcloud_mcp_server.client.base import BaseNextcloudClient
+
+
+class WebhooksClient(BaseNextcloudClient):
+    """Client for Nextcloud webhook_listeners app API operations."""
+
+    app_name = "webhooks"
+
+    def _get_webhook_headers(
+        self, additional_headers: Optional[Dict[str, str]] = None
+    ) -> Dict[str, str]:
+        """Get standard headers required for Webhook Listeners API calls."""
+        headers = {"OCS-APIRequest": "true", "Accept": "application/json"}
+        if additional_headers:
+            headers.update(additional_headers)
+        return headers
+
+    async def list_webhooks(self) -> List[Dict[str, Any]]:
+        """List all registered webhooks for the current user.
+
+        Returns:
+            List of webhook registrations with id, uri, event, filters, etc.
+        """
+        headers = self._get_webhook_headers()
+        response = await self._make_request(
+            "GET",
+            "/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks",
+            headers=headers,
+        )
+        data = response.json()["ocs"]["data"]
+        return data if isinstance(data, list) else []
+
+    async def create_webhook(
+        self,
+        event: str,
+        uri: str,
+        http_method: str = "POST",
+        auth_method: str = "none",
+        headers: Optional[Dict[str, str]] = None,
+        event_filter: Optional[Dict[str, Any]] = None,
+    ) -> Dict[str, Any]:
+        """Register a new webhook for the specified event.
+
+        Args:
+            event: Fully qualified event class name (e.g., "OCP\\Files\\Events\\Node\\NodeCreatedEvent")
+            uri: Webhook endpoint URL to receive event notifications
+            http_method: HTTP method for webhook delivery (default: "POST")
+            auth_method: Authentication method ("none", "bearer", etc.)
+            headers: Custom headers to include in webhook requests (e.g., Authorization header)
+            event_filter: JSON object specifying event filters (e.g., {"user.uid": "bob"})
+
+        Returns:
+            Webhook registration details including webhook ID
+        """
+        data: Dict[str, Any] = {
+            "httpMethod": http_method,
+            "uri": uri,
+            "event": event,
+            "authMethod": auth_method,
+        }
+
+        if headers:
+            data["headers"] = headers
+
+        if event_filter:
+            data["eventFilter"] = event_filter
+
+        request_headers = self._get_webhook_headers()
+        response = await self._make_request(
+            "POST",
+            "/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks",
+            json=data,
+            headers=request_headers,
+        )
+        return response.json()["ocs"]["data"]
+
+    async def delete_webhook(self, webhook_id: int) -> None:
+        """Delete a webhook registration.
+
+        Args:
+            webhook_id: ID of the webhook to delete
+        """
+        headers = self._get_webhook_headers()
+        await self._make_request(
+            "DELETE",
+            f"/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks/{webhook_id}",
+            headers=headers,
+        )
+
+    async def get_webhook(self, webhook_id: int) -> Dict[str, Any]:
+        """Get details of a specific webhook registration.
+
+        Args:
+            webhook_id: ID of the webhook to retrieve
+
+        Returns:
+            Webhook registration details
+        """
+        headers = self._get_webhook_headers()
+        response = await self._make_request(
+            "GET",
+            f"/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks/{webhook_id}",
+            headers=headers,
+        )
+        return response.json()["ocs"]["data"]
@@ -153,7 +153,13 @@ class Settings:
    # Token exchange cache settings
    token_exchange_cache_ttl: int = 300  # seconds (5 minutes default)

-    # Token settings
+    # Token and webhook storage settings
+    # TOKEN_ENCRYPTION_KEY: Optional - Only required for OAuth token storage operations.
+    #                       Webhook tracking works without encryption key.
+    #                       If set, must be a valid base64-encoded Fernet key (32 bytes).
+    # TOKEN_STORAGE_DB: Path to SQLite database for persistent storage.
+    #                   Used for webhook tracking (all modes) and OAuth token storage.
+    #                   Defaults to /tmp/tokens.db
    token_encryption_key: Optional[str] = None
    token_storage_db: Optional[str] = None

@@ -181,12 +187,12 @@ class Settings:
    # Observability settings
    metrics_enabled: bool = True
    metrics_port: int = 9090
-    tracing_enabled: bool = False
    otel_exporter_otlp_endpoint: Optional[str] = None
+    otel_exporter_verify_ssl: bool = False
    otel_service_name: str = "nextcloud-mcp-server"
    otel_traces_sampler: str = "always_on"
    otel_traces_sampler_arg: float = 1.0
-    log_format: str = "json"  # "json" or "text"
+    log_format: str = "text"  # "json" or "text"
    log_level: str = "INFO"
    log_include_trace_context: bool = True

@@ -204,7 +210,7 @@ class Settings:
        # Default to :memory: if neither set
        if not self.qdrant_url and not self.qdrant_location:
            self.qdrant_location = ":memory:"
-            logger.info("Using default Qdrant mode: in-memory (:memory:)")
+            logger.debug("Using default Qdrant mode: in-memory (:memory:)")

        # Warn if API key set in local mode
        if self.qdrant_location and self.qdrant_api_key:
@@ -305,7 +311,7 @@ def get_settings() -> Settings:
        ),
        # Token exchange cache settings
        token_exchange_cache_ttl=int(os.getenv("TOKEN_EXCHANGE_CACHE_TTL", "300")),
-        # Token settings
+        # Token and webhook storage settings (encryption key optional for webhook-only usage)
        token_encryption_key=os.getenv("TOKEN_ENCRYPTION_KEY"),
        token_storage_db=os.getenv("TOKEN_STORAGE_DB", "/tmp/tokens.db"),
        # Vector sync settings (ADR-007)
@@ -334,12 +340,13 @@ def get_settings() -> Settings:
        # Observability settings
        metrics_enabled=os.getenv("METRICS_ENABLED", "true").lower() == "true",
        metrics_port=int(os.getenv("METRICS_PORT", "9090")),
-        tracing_enabled=os.getenv("OTEL_ENABLED", "false").lower() == "true",
        otel_exporter_otlp_endpoint=os.getenv("OTEL_EXPORTER_OTLP_ENDPOINT"),
+        otel_exporter_verify_ssl=os.getenv("OTEL_EXPORTER_VERIFY_SSL", "false").lower()
+        == "true",
        otel_service_name=os.getenv("OTEL_SERVICE_NAME", "nextcloud-mcp-server"),
        otel_traces_sampler=os.getenv("OTEL_TRACES_SAMPLER", "always_on"),
        otel_traces_sampler_arg=float(os.getenv("OTEL_TRACES_SAMPLER_ARG", "1.0")),
-        log_format=os.getenv("LOG_FORMAT", "json"),
+        log_format=os.getenv("LOG_FORMAT", "text"),
        log_level=os.getenv("LOG_LEVEL", "INFO"),
        log_include_trace_context=os.getenv("LOG_INCLUDE_TRACE_CONTEXT", "true").lower()
        == "true",
@@ -12,13 +12,24 @@ class NotesSearchController:
        """
        Search notes using token-based matching with relevance ranking.
        Returns notes sorted by relevance score.
+        If query is empty, returns all notes.
        """
        search_results = []
        query_tokens = self._process_query(query)

-        # If empty query after processing, return empty results
+        # If empty query after processing, return all notes
        if not query_tokens:
-            return []
+            async for note in notes:
+                search_results.append(
+                    {
+                        "id": note.get("id"),
+                        "title": note.get("title"),
+                        "category": note.get("category"),
+                        "modified": note.get("modified"),
+                        "_score": None,  # No score for unfiltered results
+                    }
+                )
+            return search_results

        # Process and score each note
        async for note in notes:
@@ -17,6 +17,7 @@ class OllamaEmbeddingProvider(EmbeddingProvider):
        base_url: str,
        model: str = "nomic-embed-text",
        verify_ssl: bool = True,
+        timeout=httpx.Timeout(timeout=120, connect=5),
    ):
        """
        Initialize Ollama embedding provider.
@@ -29,12 +30,14 @@ class OllamaEmbeddingProvider(EmbeddingProvider):
        self.base_url = base_url.rstrip("/")
        self.model = model
        self.verify_ssl = verify_ssl
-        self.client = httpx.AsyncClient(verify=verify_ssl, timeout=30.0)
-        self._dimension = 768  # nomic-embed-text default
+        self.client = httpx.AsyncClient(verify=verify_ssl, timeout=timeout)
+        self._dimension: int | None = None  # Will be detected dynamically
        logger.info(
            f"Initialized Ollama provider: {base_url} (model={model}, verify_ssl={verify_ssl})"
        )

+        self._check_model_is_loaded(autoload=True)
+
    async def embed(self, text: str) -> list[float]:
        """
        Generate embedding vector for text.
@@ -71,15 +74,55 @@ class OllamaEmbeddingProvider(EmbeddingProvider):
            embeddings.append(embedding)
        return embeddings

+    async def _detect_dimension(self):
+        """
+        Detect embedding dimension by generating a test embedding.
+
+        This method queries the model to determine the actual dimension
+        instead of relying on hardcoded values.
+        """
+        if self._dimension is None:
+            logger.debug(f"Detecting embedding dimension for model {self.model}...")
+            test_embedding = await self.embed("test")
+            self._dimension = len(test_embedding)
+            logger.info(
+                f"Detected embedding dimension: {self._dimension} for model {self.model}"
+            )
+
    def get_dimension(self) -> int:
        """
        Get embedding dimension.

        Returns:
-            Vector dimension (768 for nomic-embed-text)
+            Vector dimension for the configured model
+
+        Raises:
+            RuntimeError: If dimension not detected yet (call _detect_dimension first)
        """
+        if self._dimension is None:
+            raise RuntimeError(
+                f"Embedding dimension not detected yet for model {self.model}. "
+                "Call _detect_dimension() first or generate an embedding."
+            )
        return self._dimension

+    def _check_model_is_loaded(self, autoload: bool = True):
+        response = httpx.get(f"{self.base_url}/api/tags")
+        response.raise_for_status()
+
+        models = [model["name"] for model in response.json().get("models", [])]
+        logger.info("Ollama has following models pre-loaded: %s", models)
+
+        if (self.model not in models) and autoload:
+            logger.warning(
+                "Embedding model '%s' not yet available in ollama, attempting to pull now...",
+                self.model,
+            )
+            response = httpx.post(
+                f"{self.base_url}/api/pull", json={"model": self.model}
+            )
+            response.raise_for_status()
+
    async def close(self):
        """Close HTTP client."""
        await self.client.aclose()
@@ -12,7 +12,7 @@ import logging
 import sys
 from typing import Any

-from pythonjsonlogger import jsonlogger
+from pythonjsonlogger.json import JsonFormatter

 from nextcloud_mcp_server.observability.tracing import get_trace_context

@@ -43,7 +43,7 @@ class HealthCheckFilter(logging.Filter):
        )


-class TraceContextFormatter(jsonlogger.JsonFormatter):
+class TraceContextFormatter(JsonFormatter):
    """
    JSON formatter that injects OpenTelemetry trace context into log records.

@@ -147,7 +147,7 @@ def setup_logging(
                datefmt="%Y-%m-%dT%H:%M:%S",
            )
        else:
-            formatter = jsonlogger.JsonFormatter(
+            formatter = JsonFormatter(
                "%(timestamp)s %(level)s %(name)s %(message)s",
                datefmt="%Y-%m-%dT%H:%M:%S",
            )
@@ -251,7 +251,7 @@ def get_uvicorn_logging_config(
        if include_trace_context:
            formatter_class = "nextcloud_mcp_server.observability.logging_config.TraceContextFormatter"
        else:
-            formatter_class = "pythonjsonlogger.jsonlogger.JsonFormatter"
+            formatter_class = "pythonjsonlogger.json.JsonFormatter"
        format_string = "%(timestamp)s %(level)s %(name)s %(message)s"
    else:
        if include_trace_context:
@@ -352,3 +352,92 @@ def record_dependency_check(dependency: str, duration: float) -> None:
        duration: Check duration in seconds
    """
    dependency_check_duration_seconds.labels(dependency=dependency).observe(duration)
+
+
+def record_vector_sync_scan(documents_found: int) -> None:
+    """
+    Record documents scanned during vector sync.
+
+    Args:
+        documents_found: Number of documents discovered in scan
+    """
+    vector_sync_documents_scanned_total.inc(documents_found)
+
+
+def record_vector_sync_processing(duration: float, status: str = "success") -> None:
+    """
+    Record document processing with duration and status.
+
+    Args:
+        duration: Processing duration in seconds
+        status: "success" or "error"
+    """
+    vector_sync_documents_processed_total.labels(status=status).inc()
+    vector_sync_processing_duration_seconds.observe(duration)
+
+
+def record_qdrant_operation(operation: str, status: str = "success") -> None:
+    """
+    Record Qdrant vector database operation.
+
+    Args:
+        operation: Operation type ("upsert", "search", "delete")
+        status: "success" or "error"
+    """
+    qdrant_operations_total.labels(operation=operation, status=status).inc()
+
+
+def update_vector_sync_queue_size(size: int) -> None:
+    """
+    Update vector sync queue size gauge.
+
+    Args:
+        size: Current queue size
+    """
+    vector_sync_queue_size.set(size)
+
+
+# =============================================================================
+# Decorator for Automatic Tool Instrumentation
+# =============================================================================
+
+
+def instrument_tool(func):
+    """
+    Decorator to automatically instrument MCP tool functions with metrics.
+
+    Wraps async tool functions to record execution time and success/error status.
+    Compatible with @mcp.tool() and @require_scopes() decorators.
+
+    Usage:
+        @mcp.tool()
+        @require_scopes("notes:write")
+        @instrument_tool
+        async def nc_notes_create_note(...):
+            ...
+
+    Args:
+        func: The async function to instrument
+
+    Returns:
+        Wrapped function with metrics instrumentation
+    """
+    import functools
+    import time
+
+    @functools.wraps(func)
+    async def wrapper(*args, **kwargs):
+        tool_name = func.__name__
+        start_time = time.time()
+        try:
+            result = await func(*args, **kwargs)
+            duration = time.time() - start_time
+            record_tool_call(tool_name, duration, "success")
+            return result
+        except Exception as e:
+            duration = time.time() - start_time
+            record_tool_call(tool_name, duration, "error")
+            record_tool_error(tool_name, type(e).__name__)
+            raise
+
+    return wrapper
@@ -66,22 +66,40 @@ class ObservabilityMiddleware(BaseHTTPMiddleware):
        # Record start time
        start_time = time.time()

-        try:
-            # Create span for request (OpenTelemetry auto-instrumentation will create parent span)
-            with trace_operation(
-                f"HTTP {method} {endpoint}",
-                attributes={
-                    "http.method": method,
-                    "http.path": path,
-                    "http.scheme": request.url.scheme,
-                    "http.host": request.url.hostname,
-                },
-            ):
-                # Process request
-                response = await call_next(request)
+        # Skip tracing for health/metrics endpoints to reduce noise
+        should_trace = not (path.startswith("/health/") or path == "/metrics")

-                # Add response status to span
-                add_span_attribute("http.status_code", response.status_code)
+        try:
+            if should_trace:
+                # Create span for request (OpenTelemetry auto-instrumentation will create parent span)
+                with trace_operation(
+                    f"HTTP {method} {endpoint}",
+                    attributes={
+                        "http.method": method,
+                        "http.path": path,
+                        "http.scheme": request.url.scheme,
+                        "http.host": request.url.hostname,
+                    },
+                ):
+                    # Process request
+                    response = await call_next(request)
+
+                    # Add response status to span
+                    add_span_attribute("http.status_code", response.status_code)
+
+                    # Record metrics
+                    duration = time.time() - start_time
+                    self._record_request_metrics(
+                        method=method,
+                        endpoint=endpoint,
+                        status_code=response.status_code,
+                        duration=duration,
+                    )
+
+                    return response
+            else:
+                # No tracing for health/metrics endpoints, but still record metrics
+                response = await call_next(request)

                # Record metrics
                duration = time.time() - start_time
@@ -13,9 +13,9 @@ import logging
 from contextlib import contextmanager
 from typing import Any

+from importlib_metadata import version
 from opentelemetry import trace
 from opentelemetry.exporter.otlp.proto.grpc.trace_exporter import OTLPSpanExporter
-from opentelemetry.instrumentation.httpx import HTTPXClientInstrumentor
 from opentelemetry.instrumentation.logging import LoggingInstrumentor
 from opentelemetry.sdk.resources import Resource
 from opentelemetry.sdk.trace import TracerProvider
@@ -27,10 +27,13 @@ logger = logging.getLogger(__name__)
 # Global tracer instance (initialized in setup_tracing)
 _tracer: Tracer | None = None

+# Auto-instrument httpx for Nextcloud API calls
+

 def setup_tracing(
    service_name: str = "nextcloud-mcp-server",
    otlp_endpoint: str | None = None,
+    otlp_verify_ssl: bool = False,
    sampling_rate: float = 1.0,
 ) -> Tracer:
    """
@@ -40,6 +43,8 @@ def setup_tracing(
        service_name: Service name for traces (default: "nextcloud-mcp-server")
        otlp_endpoint: OTLP gRPC endpoint (e.g., "http://otel-collector:4317")
                      If None, tracing is initialized but no exporter is configured
+        otlp_verify_ssl: Enable TLS verification for otlp_endpoint. If True,
+                      `insecure` will eval to False
        sampling_rate: Sampling rate (0.0-1.0). Default 1.0 (100% sampling)

    Returns:
@@ -51,7 +56,7 @@ def setup_tracing(
    resource = Resource.create(
        {
            "service.name": service_name,
-            "service.version": "0.27.2",  # TODO: Extract from pyproject.toml
+            "service.version": version(__package__.split(".")[0]),
        }
    )

@@ -61,7 +66,9 @@ def setup_tracing(
    # Configure OTLP exporter if endpoint is provided
    if otlp_endpoint:
        try:
-            otlp_exporter = OTLPSpanExporter(endpoint=otlp_endpoint, insecure=True)
+            otlp_exporter = OTLPSpanExporter(
+                endpoint=otlp_endpoint, insecure=not otlp_verify_ssl
+            )
            span_processor = BatchSpanProcessor(otlp_exporter)
            provider.add_span_processor(span_processor)
            logger.info(
@@ -79,9 +86,6 @@ def setup_tracing(
    # Set global tracer provider
    trace.set_tracer_provider(provider)

-    # Auto-instrument httpx for Nextcloud API calls
-    HTTPXClientInstrumentor().instrument()
-
    # Auto-instrument logging to inject trace context
    LoggingInstrumentor().instrument(set_logging_format=True)

@@ -12,6 +12,7 @@ from nextcloud_mcp_server.models.calendar import (
    ListTodosResponse,
    Todo,
 )
+from nextcloud_mcp_server.observability.metrics import instrument_tool

 logger = logging.getLogger(__name__)

@@ -20,6 +21,7 @@ def configure_calendar_tools(mcp: FastMCP):
    # Calendar tools
    @mcp.tool()
    @require_scopes("calendar:read")
+    @instrument_tool
    async def nc_calendar_list_calendars(ctx: Context) -> ListCalendarsResponse:
        """List all available calendars for the user"""
        client = await get_client(ctx)
@@ -30,6 +32,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:write")
+    @instrument_tool
    async def nc_calendar_create_event(
        calendar_name: str,
        title: str,
@@ -106,6 +109,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:read")
+    @instrument_tool
    async def nc_calendar_list_events(
        calendar_name: str,
        ctx: Context,
@@ -208,6 +212,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:read")
+    @instrument_tool
    async def nc_calendar_get_event(
        calendar_name: str,
        event_uid: str,
@@ -220,6 +225,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:write")
+    @instrument_tool
    async def nc_calendar_update_event(
        calendar_name: str,
        event_uid: str,
@@ -293,6 +299,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:write")
+    @instrument_tool
    async def nc_calendar_delete_event(
        calendar_name: str,
        event_uid: str,
@@ -304,6 +311,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:write")
+    @instrument_tool
    async def nc_calendar_create_meeting(
        title: str,
        date: str,
@@ -370,6 +378,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:read")
+    @instrument_tool
    async def nc_calendar_get_upcoming_events(
        ctx: Context,
        calendar_name: str = "",  # Empty = all calendars
@@ -420,6 +429,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:read")
+    @instrument_tool
    async def nc_calendar_find_availability(
        duration_minutes: int,
        ctx: Context,
@@ -500,6 +510,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:write")
+    @instrument_tool
    async def nc_calendar_bulk_operations(
        operation: str,  # "update", "delete", "move"
        ctx: Context,
@@ -749,6 +760,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("calendar:write")
+    @instrument_tool
    async def nc_calendar_manage_calendar(
        action: str,  # "create", "delete", "update", "list"
        ctx: Context,
@@ -818,6 +830,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("todo:read", "calendar:read")
+    @instrument_tool
    async def nc_calendar_list_todos(
        calendar_name: str,
        ctx: Context,
@@ -863,6 +876,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("todo:write", "calendar:read")
+    @instrument_tool
    async def nc_calendar_create_todo(
        calendar_name: str,
        summary: str,
@@ -906,6 +920,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("todo:write", "calendar:read")
+    @instrument_tool
    async def nc_calendar_update_todo(
        calendar_name: str,
        todo_uid: str,
@@ -966,6 +981,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("todo:write", "calendar:read")
+    @instrument_tool
    async def nc_calendar_delete_todo(
        calendar_name: str,
        todo_uid: str,
@@ -986,6 +1002,7 @@ def configure_calendar_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("todo:read", "calendar:read")
+    @instrument_tool
    async def nc_calendar_search_todos(
        ctx: Context,
        status: Optional[str] = None,
@@ -4,6 +4,7 @@ from mcp.server.fastmcp import Context, FastMCP

 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
+from nextcloud_mcp_server.observability.metrics import instrument_tool

 logger = logging.getLogger(__name__)

@@ -12,6 +13,7 @@ def configure_contacts_tools(mcp: FastMCP):
    # Contacts tools
    @mcp.tool()
    @require_scopes("contacts:read")
+    @instrument_tool
    async def nc_contacts_list_addressbooks(ctx: Context):
        """List all addressbooks for the user."""
        client = await get_client(ctx)
@@ -19,6 +21,7 @@ def configure_contacts_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("contacts:read")
+    @instrument_tool
    async def nc_contacts_list_contacts(ctx: Context, *, addressbook: str):
        """List all contacts in the specified addressbook."""
        client = await get_client(ctx)
@@ -26,6 +29,7 @@ def configure_contacts_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("contacts:write")
+    @instrument_tool
    async def nc_contacts_create_addressbook(
        ctx: Context, *, name: str, display_name: str
    ):
@@ -42,6 +46,7 @@ def configure_contacts_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("contacts:write")
+    @instrument_tool
    async def nc_contacts_delete_addressbook(ctx: Context, *, name: str):
        """Delete an addressbook."""
        client = await get_client(ctx)
@@ -49,6 +54,7 @@ def configure_contacts_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("contacts:write")
+    @instrument_tool
    async def nc_contacts_create_contact(
        ctx: Context, *, addressbook: str, uid: str, contact_data: dict
    ):
@@ -66,6 +72,7 @@ def configure_contacts_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("contacts:write")
+    @instrument_tool
    async def nc_contacts_delete_contact(ctx: Context, *, addressbook: str, uid: str):
        """Delete a contact."""
        client = await get_client(ctx)
@@ -73,6 +80,7 @@ def configure_contacts_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("contacts:write")
+    @instrument_tool
    async def nc_contacts_update_contact(
        ctx: Context, *, addressbook: str, uid: str, contact_data: dict, etag: str = ""
    ):
@@ -24,6 +24,7 @@ from nextcloud_mcp_server.models.cookbook import (
    UpdateRecipeResponse,
    Version,
 )
+from nextcloud_mcp_server.observability.metrics import instrument_tool

 logger = logging.getLogger(__name__)

@@ -72,6 +73,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:write")
+    @instrument_tool
    async def nc_cookbook_import_recipe(url: str, ctx: Context) -> ImportRecipeResponse:
        """Import a recipe from a URL using schema.org metadata.

@@ -129,6 +131,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:read")
+    @instrument_tool
    async def nc_cookbook_list_recipes(ctx: Context) -> ListRecipesResponse:
        """Get all recipes in the database"""
        client = await get_client(ctx)
@@ -154,6 +157,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:read")
+    @instrument_tool
    async def nc_cookbook_get_recipe(recipe_id: int, ctx: Context) -> Recipe:
        """Get a specific recipe by its ID"""
        client = await get_client(ctx)
@@ -179,6 +183,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:write")
+    @instrument_tool
    async def nc_cookbook_create_recipe(
        name: str,
        description: str | None = None,
@@ -258,6 +263,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:write")
+    @instrument_tool
    async def nc_cookbook_update_recipe(
        recipe_id: int,
        name: str | None = None,
@@ -347,6 +353,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:write")
+    @instrument_tool
    async def nc_cookbook_delete_recipe(
        recipe_id: int, ctx: Context
    ) -> DeleteRecipeResponse:
@@ -382,6 +389,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:read")
+    @instrument_tool
    async def nc_cookbook_search_recipes(
        query: str, ctx: Context
    ) -> SearchRecipesResponse:
@@ -418,6 +426,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:read")
+    @instrument_tool
    async def nc_cookbook_list_categories(ctx: Context) -> ListCategoriesResponse:
        """Get all known categories.

@@ -445,6 +454,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:read")
+    @instrument_tool
    async def nc_cookbook_get_recipes_in_category(
        category: str, ctx: Context
    ) -> ListRecipesResponse:
@@ -481,6 +491,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:read")
+    @instrument_tool
    async def nc_cookbook_list_keywords(ctx: Context) -> ListKeywordsResponse:
        """Get all known keywords/tags"""
        client = await get_client(ctx)
@@ -506,6 +517,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:read")
+    @instrument_tool
    async def nc_cookbook_get_recipes_with_keywords(
        keywords: list[str], ctx: Context
    ) -> ListRecipesResponse:
@@ -540,6 +552,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:write")
+    @instrument_tool
    async def nc_cookbook_set_config(
        folder: str | None = None,
        update_interval: int | None = None,
@@ -583,6 +596,7 @@ def configure_cookbook_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("cookbook:write")
+    @instrument_tool
    async def nc_cookbook_reindex(ctx: Context) -> ReindexResponse:
        """Trigger a rescan of all recipes into the caching database.

@@ -18,6 +18,7 @@ from nextcloud_mcp_server.models.deck import (
    LabelOperationResponse,
    StackOperationResponse,
 )
+from nextcloud_mcp_server.observability.metrics import instrument_tool

 logger = logging.getLogger(__name__)

@@ -118,6 +119,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_boards(ctx: Context) -> list[DeckBoard]:
        """Get all Nextcloud Deck boards"""
        client = await get_client(ctx)
@@ -126,6 +128,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_board(ctx: Context, board_id: int) -> DeckBoard:
        """Get details of a specific Nextcloud Deck board"""
        client = await get_client(ctx)
@@ -134,6 +137,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_stacks(ctx: Context, board_id: int) -> list[DeckStack]:
        """Get all stacks in a Nextcloud Deck board"""
        client = await get_client(ctx)
@@ -142,6 +146,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_stack(ctx: Context, board_id: int, stack_id: int) -> DeckStack:
        """Get details of a specific Nextcloud Deck stack"""
        client = await get_client(ctx)
@@ -150,6 +155,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_cards(
        ctx: Context, board_id: int, stack_id: int
    ) -> list[DeckCard]:
@@ -162,6 +168,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int
    ) -> DeckCard:
@@ -172,6 +179,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_labels(ctx: Context, board_id: int) -> list[DeckLabel]:
        """Get all labels in a Nextcloud Deck board"""
        client = await get_client(ctx)
@@ -180,6 +188,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:read")
+    @instrument_tool
    async def deck_get_label(ctx: Context, board_id: int, label_id: int) -> DeckLabel:
        """Get details of a specific Nextcloud Deck label"""
        client = await get_client(ctx)
@@ -190,6 +199,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_create_board(
        ctx: Context, title: str, color: str
    ) -> CreateBoardResponse:
@@ -207,6 +217,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_create_stack(
        ctx: Context, board_id: int, title: str, order: int
    ) -> CreateStackResponse:
@@ -223,6 +234,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_update_stack(
        ctx: Context,
        board_id: int,
@@ -249,6 +261,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_delete_stack(
        ctx: Context, board_id: int, stack_id: int
    ) -> StackOperationResponse:
@@ -270,6 +283,7 @@ def configure_deck_tools(mcp: FastMCP):
    # Card Tools
    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_create_card(
        ctx: Context,
        board_id: int,
@@ -304,6 +318,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_update_card(
        ctx: Context,
        board_id: int,
@@ -357,6 +372,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_delete_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int
    ) -> CardOperationResponse:
@@ -379,6 +395,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_archive_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int
    ) -> CardOperationResponse:
@@ -401,6 +418,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_unarchive_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int
    ) -> CardOperationResponse:
@@ -423,6 +441,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_reorder_card(
        ctx: Context,
        board_id: int,
@@ -455,6 +474,7 @@ def configure_deck_tools(mcp: FastMCP):
    # Label Tools
    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_create_label(
        ctx: Context, board_id: int, title: str, color: str
    ) -> CreateLabelResponse:
@@ -471,6 +491,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_update_label(
        ctx: Context,
        board_id: int,
@@ -497,6 +518,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_delete_label(
        ctx: Context, board_id: int, label_id: int
    ) -> LabelOperationResponse:
@@ -518,6 +540,7 @@ def configure_deck_tools(mcp: FastMCP):
    # Card-Label Assignment Tools
    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_assign_label_to_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int, label_id: int
    ) -> CardOperationResponse:
@@ -541,6 +564,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_remove_label_from_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int, label_id: int
    ) -> CardOperationResponse:
@@ -565,6 +589,7 @@ def configure_deck_tools(mcp: FastMCP):
    # Card-User Assignment Tools
    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_assign_user_to_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int, user_id: str
    ) -> CardOperationResponse:
@@ -588,6 +613,7 @@ def configure_deck_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("deck:write")
+    @instrument_tool
    async def deck_unassign_user_from_card(
        ctx: Context, board_id: int, stack_id: int, card_id: int, user_id: str
    ) -> CardOperationResponse:
@@ -17,6 +17,7 @@ from nextcloud_mcp_server.models.notes import (
    SearchNotesResponse,
    UpdateNoteResponse,
 )
+from nextcloud_mcp_server.observability.metrics import instrument_tool

 logger = logging.getLogger(__name__)

@@ -86,6 +87,7 @@ def configure_notes_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("notes:write")
+    @instrument_tool
    async def nc_notes_create_note(
        title: str, content: str, category: str, ctx: Context
    ) -> CreateNoteResponse:
@@ -132,6 +134,7 @@ def configure_notes_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("notes:write")
+    @instrument_tool
    async def nc_notes_update_note(
        note_id: int,
        etag: str,
@@ -197,6 +200,7 @@ def configure_notes_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("notes:write")
+    @instrument_tool
    async def nc_notes_append_content(
        note_id: int, content: str, ctx: Context
    ) -> AppendContentResponse:
@@ -247,6 +251,7 @@ def configure_notes_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("notes:read")
+    @instrument_tool
    async def nc_notes_search_notes(query: str, ctx: Context) -> SearchNotesResponse:
        """Search notes by title or content, returning only id, title, and category (requires notes:read scope)."""
        client = await get_client(ctx)
@@ -293,6 +298,7 @@ def configure_notes_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("notes:read")
+    @instrument_tool
    async def nc_notes_get_note(note_id: int, ctx: Context) -> Note:
        """Get a specific note by its ID (requires notes:read scope)"""
        client = await get_client(ctx)
@@ -322,6 +328,7 @@ def configure_notes_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("notes:read")
+    @instrument_tool
    async def nc_notes_get_attachment(
        note_id: int, attachment_filename: str, ctx: Context
    ) -> dict[str, str]:
@@ -368,6 +375,7 @@ def configure_notes_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("notes:write")
+    @instrument_tool
    async def nc_notes_delete_note(note_id: int, ctx: Context) -> DeleteNoteResponse:
        """Delete a note permanently"""
        logger.info("Deleting note %s", note_id)
@@ -18,7 +18,7 @@ from mcp.server.fastmcp import Context
 from pydantic import BaseModel, Field

 from nextcloud_mcp_server.auth import require_scopes
-from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
 from nextcloud_mcp_server.auth.userinfo_routes import _query_idp_userinfo

@@ -21,6 +21,10 @@ from nextcloud_mcp_server.models.semantic import (
    SemanticSearchResult,
    VectorSyncStatusResponse,
 )
+from nextcloud_mcp_server.observability.metrics import (
+    instrument_tool,
+    record_qdrant_operation,
+)

 logger = logging.getLogger(__name__)

@@ -30,6 +34,7 @@ def configure_semantic_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("semantic:read")
+    @instrument_tool
    async def nc_semantic_search(
        query: str, ctx: Context, limit: int = 10, score_threshold: float = 0.7
    ) -> SemanticSearchResponse:
@@ -85,26 +90,33 @@ def configure_semantic_tools(mcp: FastMCP):
            # Note: Currently only searching notes (doc_type="note")
            # Future: Remove doc_type filter to search all apps
            qdrant_client = await get_qdrant_client()
-            search_response = await qdrant_client.query_points(
-                collection_name=settings.get_collection_name(),
-                query=query_embedding,
-                query_filter=Filter(
-                    must=[
-                        FieldCondition(
-                            key="user_id",
-                            match=MatchValue(value=username),
-                        ),
-                        FieldCondition(
-                            key="doc_type",
-                            match=MatchValue(value="note"),
-                        ),
-                    ]
-                ),
-                limit=limit * 2,  # Get extra for filtering
-                score_threshold=score_threshold,
-                with_payload=True,
-                with_vectors=False,  # Don't return vectors to save bandwidth
-            )
+            try:
+                search_response = await qdrant_client.query_points(
+                    collection_name=settings.get_collection_name(),
+                    query=query_embedding,
+                    query_filter=Filter(
+                        must=[
+                            FieldCondition(
+                                key="user_id",
+                                match=MatchValue(value=username),
+                            ),
+                            FieldCondition(
+                                key="doc_type",
+                                match=MatchValue(value="note"),
+                            ),
+                        ]
+                    ),
+                    limit=limit * 2,  # Get extra for filtering
+                    score_threshold=score_threshold,
+                    with_payload=True,
+                    with_vectors=False,  # Don't return vectors to save bandwidth
+                )
+                # Record successful search operation
+                record_qdrant_operation("search", "success")
+            except Exception:
+                # Record failed search operation
+                record_qdrant_operation("search", "error")
+                raise

            logger.info(
                f"Qdrant returned {len(search_response.points)} results "
@@ -208,6 +220,7 @@ def configure_semantic_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("semantic:read")
+    @instrument_tool
    async def nc_semantic_search_answer(
        query: str,
        ctx: Context,
@@ -331,21 +344,71 @@ def configure_semantic_tools(mcp: FastMCP):
                success=True,
            )

-        # 4. Construct context from retrieved documents
+        # 4. Fetch full content for notes to provide complete context to LLM
+        # Filter out inaccessible notes (deleted or permissions changed)
+        client = await get_client(ctx)
+        accessible_results = []
+        full_contents = []  # Full content for accessible notes
+
+        for result in search_response.results:
+            if result.doc_type == "note":
+                try:
+                    note = await client.notes.get_note(result.id)
+                    # Note is accessible, store full content
+                    accessible_results.append(result)
+                    full_contents.append(note.get("content", ""))
+                    logger.debug(
+                        f"Fetched full content for note {result.id} "
+                        f"(length: {len(full_contents[-1])} chars)"
+                    )
+                except Exception as e:
+                    # Note might have been deleted or permissions changed
+                    # Filter it out to avoid corrupting LLM with inaccessible data
+                    logger.warning(
+                        f"Failed to fetch full content for note {result.id}: {e}. "
+                        f"Excluding from results."
+                    )
+            else:
+                # Non-note document types (future: calendar, deck, files)
+                # For now, keep them with excerpts
+                accessible_results.append(result)
+                full_contents.append(None)
+
+        # Check if we filtered out all results
+        if not accessible_results:
+            logger.warning(f"All search results became inaccessible for query: {query}")
+            return SamplingSearchResponse(
+                query=query,
+                generated_answer="All matching documents are no longer accessible.",
+                sources=[],
+                total_found=0,
+                search_method="semantic_sampling",
+                success=True,
+            )
+
+        # 5. Construct context from accessible documents with full content
        context_parts = []
-        for idx, result in enumerate(search_response.results, 1):
+        for idx, (result, content) in enumerate(
+            zip(accessible_results, full_contents), 1
+        ):
+            # Use full content if available (notes), otherwise use excerpt
+            if content is not None:
+                content_field = f"Content: {content}"
+            else:
+                content_field = f"Excerpt: {result.excerpt}"
+
            context_parts.append(
                f"[Document {idx}]\n"
                f"Type: {result.doc_type}\n"
                f"Title: {result.title}\n"
                f"Category: {result.category}\n"
-                f"Excerpt: {result.excerpt}\n"
+                f"{content_field}\n"
                f"Relevance Score: {result.score:.2f}\n"
            )

        context = "\n".join(context_parts)

-        # 5. Construct prompt - reuse user's query, add context and instructions
+        # 6. Construct prompt - reuse user's query, add context and instructions
        prompt = (
            f"{query}\n\n"
            f"Here are relevant documents from Nextcloud (notes, calendar events, deck cards, files, contacts):\n\n"
@@ -401,8 +464,8 @@ def configure_semantic_tools(mcp: FastMCP):
            return SamplingSearchResponse(
                query=query,
                generated_answer=generated_answer,
-                sources=search_response.results,
-                total_found=search_response.total_found,
+                sources=accessible_results,
+                total_found=len(accessible_results),
                search_method="semantic_sampling",
                model_used=sampling_result.model,
                stop_reason=sampling_result.stopReason,
@@ -419,11 +482,11 @@ def configure_semantic_tools(mcp: FastMCP):
                generated_answer=(
                    f"[Sampling request timed out]\n\n"
                    f"The answer generation took too long (>30s). "
-                    f"Found {search_response.total_found} relevant documents. "
+                    f"Found {len(accessible_results)} relevant documents. "
                    f"Please review the sources below or try a simpler query."
                ),
-                sources=search_response.results,
-                total_found=search_response.total_found,
+                sources=accessible_results,
+                total_found=len(accessible_results),
                search_method="semantic_sampling_timeout",
                success=True,
            )
@@ -454,11 +517,11 @@ def configure_semantic_tools(mcp: FastMCP):
                query=query,
                generated_answer=(
                    f"[{user_message}]\n\n"
-                    f"Found {search_response.total_found} relevant documents. "
+                    f"Found {len(accessible_results)} relevant documents. "
                    f"Please review the sources below."
                ),
-                sources=search_response.results,
-                total_found=search_response.total_found,
+                sources=accessible_results,
+                total_found=len(accessible_results),
                search_method=search_method,
                success=True,
            )
@@ -475,17 +538,18 @@ def configure_semantic_tools(mcp: FastMCP):
                query=query,
                generated_answer=(
                    f"[Unexpected error during sampling]\n\n"
-                    f"Found {search_response.total_found} relevant documents. "
+                    f"Found {len(accessible_results)} relevant documents. "
                    f"Please review the sources below."
                ),
-                sources=search_response.results,
-                total_found=search_response.total_found,
+                sources=accessible_results,
+                total_found=len(accessible_results),
                search_method="semantic_sampling_error",
                success=True,
            )

    @mcp.tool()
    @require_scopes("semantic:read")
+    @instrument_tool
    async def nc_get_vector_sync_status(ctx: Context) -> VectorSyncStatusResponse:
        """Get the current vector sync status.

@@ -6,6 +6,7 @@ from mcp.server.fastmcp import Context, FastMCP

 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
+from nextcloud_mcp_server.observability.metrics import instrument_tool


 def configure_sharing_tools(mcp: FastMCP):
@@ -17,6 +18,7 @@ def configure_sharing_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("sharing:write")
+    @instrument_tool
    async def nc_share_create(
        path: str,
        share_with: str,
@@ -56,6 +58,7 @@ def configure_sharing_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("sharing:write")
+    @instrument_tool
    async def nc_share_delete(share_id: int, ctx: Context) -> str:
        """Delete a share by its ID.

@@ -75,6 +78,7 @@ def configure_sharing_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("sharing:write")
+    @instrument_tool
    async def nc_share_get(share_id: int, ctx: Context) -> str:
        """Get information about a specific share.

@@ -93,6 +97,7 @@ def configure_sharing_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("sharing:write")
+    @instrument_tool
    async def nc_share_list(
        ctx: Context, path: str | None = None, shared_with_me: bool = False
    ) -> str:
@@ -114,6 +119,7 @@ def configure_sharing_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("sharing:write")
+    @instrument_tool
    async def nc_share_update(share_id: int, permissions: int, ctx: Context) -> str:
        """Update the permissions of an existing share.

@@ -4,6 +4,7 @@ from mcp.server.fastmcp import Context, FastMCP

 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
+from nextcloud_mcp_server.observability.metrics import instrument_tool

 logger = logging.getLogger(__name__)

@@ -12,6 +13,7 @@ def configure_tables_tools(mcp: FastMCP):
    # Tables tools
    @mcp.tool()
    @require_scopes("tables:read")
+    @instrument_tool
    async def nc_tables_list_tables(ctx: Context):
        """List all tables available to the user"""
        client = await get_client(ctx)
@@ -19,6 +21,7 @@ def configure_tables_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("tables:read")
+    @instrument_tool
    async def nc_tables_get_schema(table_id: int, ctx: Context):
        """Get the schema/structure of a specific table including columns and views"""
        client = await get_client(ctx)
@@ -26,6 +29,7 @@ def configure_tables_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("tables:read")
+    @instrument_tool
    async def nc_tables_read_table(
        table_id: int,
        ctx: Context,
@@ -38,6 +42,7 @@ def configure_tables_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("tables:write")
+    @instrument_tool
    async def nc_tables_insert_row(table_id: int, data: dict, ctx: Context):
        """Insert a new row into a table.

@@ -48,6 +53,7 @@ def configure_tables_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("tables:write")
+    @instrument_tool
    async def nc_tables_update_row(row_id: int, data: dict, ctx: Context):
        """Update an existing row in a table.

@@ -58,6 +64,7 @@ def configure_tables_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("tables:write")
+    @instrument_tool
    async def nc_tables_delete_row(row_id: int, ctx: Context):
        """Delete a row from a table"""
        client = await get_client(ctx)
@@ -5,6 +5,7 @@ from mcp.server.fastmcp import Context, FastMCP
 from nextcloud_mcp_server.auth import require_scopes
 from nextcloud_mcp_server.context import get_client
 from nextcloud_mcp_server.models import DirectoryListing, FileInfo, SearchFilesResponse
+from nextcloud_mcp_server.observability.metrics import instrument_tool
 from nextcloud_mcp_server.utils.document_parser import (
    is_parseable_document,
    parse_document,
@@ -17,6 +18,7 @@ def configure_webdav_tools(mcp: FastMCP):
    # WebDAV file system tools
    @mcp.tool()
    @require_scopes("files:read")
+    @instrument_tool
    async def nc_webdav_list_directory(
        ctx: Context, path: str = ""
    ) -> DirectoryListing:
@@ -50,6 +52,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:read")
+    @instrument_tool
    async def nc_webdav_read_file(path: str, ctx: Context):
        """Read the content of a file from NextCloud.

@@ -130,6 +133,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:write")
+    @instrument_tool
    async def nc_webdav_write_file(
        path: str, content: str, ctx: Context, content_type: str | None = None
    ):
@@ -158,6 +162,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:write")
+    @instrument_tool
    async def nc_webdav_create_directory(path: str, ctx: Context):
        """Create a directory in NextCloud.

@@ -172,6 +177,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:write")
+    @instrument_tool
    async def nc_webdav_delete_resource(path: str, ctx: Context):
        """Delete a file or directory in NextCloud.

@@ -186,6 +192,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:write")
+    @instrument_tool
    async def nc_webdav_move_resource(
        source_path: str, destination_path: str, ctx: Context, overwrite: bool = False
    ):
@@ -206,6 +213,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:write")
+    @instrument_tool
    async def nc_webdav_copy_resource(
        source_path: str, destination_path: str, ctx: Context, overwrite: bool = False
    ):
@@ -226,6 +234,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:read")
+    @instrument_tool
    async def nc_webdav_search_files(
        ctx: Context,
        scope: str = "",
@@ -342,6 +351,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:read")
+    @instrument_tool
    async def nc_webdav_find_by_name(
        pattern: str, ctx: Context, scope: str = "", limit: int | None = None
    ) -> SearchFilesResponse:
@@ -369,6 +379,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:read")
+    @instrument_tool
    async def nc_webdav_find_by_type(
        mime_type: str, ctx: Context, scope: str = "", limit: int | None = None
    ) -> SearchFilesResponse:
@@ -396,6 +407,7 @@ def configure_webdav_tools(mcp: FastMCP):

    @mcp.tool()
    @require_scopes("files:read")
+    @instrument_tool
    async def nc_webdav_list_favorites(
        ctx: Context, scope: str = "", limit: int | None = None
    ) -> SearchFilesResponse:
@@ -0,0 +1,197 @@
+"""Webhook preset configurations for common sync scenarios.
+
+This module defines pre-configured webhook bundles that simplify
+webhook setup for common use cases like Notes sync, Calendar sync, etc.
+"""
+
+from typing import Any, Dict, List, TypedDict
+
+
+class WebhookEventConfig(TypedDict):
+    """Configuration for a single webhook event."""
+
+    event: str  # Fully qualified event class name
+    filter: Dict[str, Any]  # Event filter (optional)
+
+
+class WebhookPreset(TypedDict):
+    """Definition of a webhook preset."""
+
+    name: str  # Display name
+    description: str  # User-friendly description
+    events: List[WebhookEventConfig]  # List of events to register
+    app: str  # Nextcloud app this preset is for
+
+
+# File/Notes webhook events
+FILE_EVENT_CREATED = "OCP\\Files\\Events\\Node\\NodeCreatedEvent"
+FILE_EVENT_WRITTEN = "OCP\\Files\\Events\\Node\\NodeWrittenEvent"
+# Use BeforeNodeDeletedEvent instead of NodeDeletedEvent to get node.id
+# See: https://github.com/nextcloud/server/issues/56371
+FILE_EVENT_DELETED = "OCP\\Files\\Events\\Node\\BeforeNodeDeletedEvent"
+
+# Calendar webhook events
+CALENDAR_EVENT_CREATED = "OCP\\Calendar\\Events\\CalendarObjectCreatedEvent"
+CALENDAR_EVENT_UPDATED = "OCP\\Calendar\\Events\\CalendarObjectUpdatedEvent"
+CALENDAR_EVENT_DELETED = "OCP\\Calendar\\Events\\CalendarObjectDeletedEvent"
+
+# Tables webhook events (Nextcloud 30+)
+TABLES_EVENT_ROW_ADDED = "OCA\\Tables\\Event\\RowAddedEvent"
+TABLES_EVENT_ROW_UPDATED = "OCA\\Tables\\Event\\RowUpdatedEvent"
+TABLES_EVENT_ROW_DELETED = "OCA\\Tables\\Event\\RowDeletedEvent"
+
+# Forms webhook events (Nextcloud 30+)
+FORMS_EVENT_FORM_SUBMITTED = "OCA\\Forms\\Events\\FormSubmittedEvent"
+
+# NOTE: Deck and Contacts do NOT support webhooks
+# Their event classes do not implement IWebhookCompatibleEvent interface.
+# Alternative sync strategies:
+# - Deck: Use polling with ETag-based change detection
+# - Contacts: Use CardDAV sync-token mechanism for efficient syncing
+
+
+WEBHOOK_PRESETS: Dict[str, WebhookPreset] = {
+    "notes_sync": {
+        "name": "Notes Sync",
+        "description": "Real-time synchronization for Notes app (create, update, delete)",
+        "app": "notes",
+        "events": [
+            {
+                "event": FILE_EVENT_CREATED,
+                "filter": {"event.node.path": "/^\\/.*\\/files\\/Notes\\//"},
+            },
+            {
+                "event": FILE_EVENT_WRITTEN,
+                "filter": {"event.node.path": "/^\\/.*\\/files\\/Notes\\//"},
+            },
+            {
+                "event": FILE_EVENT_DELETED,
+                "filter": {"event.node.path": "/^\\/.*\\/files\\/Notes\\//"},
+            },
+        ],
+    },
+    "calendar_sync": {
+        "name": "Calendar Sync",
+        "description": "Real-time synchronization for Calendar events (create, update, delete)",
+        "app": "calendar",
+        "events": [
+            {
+                "event": CALENDAR_EVENT_CREATED,
+                "filter": {},
+            },
+            {
+                "event": CALENDAR_EVENT_UPDATED,
+                "filter": {},
+            },
+            {
+                "event": CALENDAR_EVENT_DELETED,
+                "filter": {},
+            },
+        ],
+    },
+    "tables_sync": {
+        "name": "Tables Sync",
+        "description": "Real-time synchronization for Tables rows (add, update, delete)",
+        "app": "tables",
+        "events": [
+            {
+                "event": TABLES_EVENT_ROW_ADDED,
+                "filter": {},
+            },
+            {
+                "event": TABLES_EVENT_ROW_UPDATED,
+                "filter": {},
+            },
+            {
+                "event": TABLES_EVENT_ROW_DELETED,
+                "filter": {},
+            },
+        ],
+    },
+    "forms_sync": {
+        "name": "Forms Sync",
+        "description": "Real-time synchronization for Forms submissions",
+        "app": "forms",
+        "events": [
+            {
+                "event": FORMS_EVENT_FORM_SUBMITTED,
+                "filter": {},
+            },
+        ],
+    },
+    "files_sync": {
+        "name": "All Files Sync",
+        "description": "Real-time synchronization for all file operations (create, update, delete)",
+        "app": "files",
+        "events": [
+            {
+                "event": FILE_EVENT_CREATED,
+                "filter": {},
+            },
+            {
+                "event": FILE_EVENT_WRITTEN,
+                "filter": {},
+            },
+            {
+                "event": FILE_EVENT_DELETED,
+                "filter": {},
+            },
+        ],
+    },
+}
+
+
+def get_preset(preset_id: str) -> WebhookPreset | None:
+    """Get a webhook preset by ID.
+
+    Args:
+        preset_id: Preset identifier (e.g., "notes_sync", "calendar_sync")
+
+    Returns:
+        Webhook preset configuration or None if not found
+    """
+    return WEBHOOK_PRESETS.get(preset_id)
+
+
+def list_presets() -> List[tuple[str, WebhookPreset]]:
+    """Get all available webhook presets.
+
+    Returns:
+        List of (preset_id, preset_config) tuples
+    """
+    return list(WEBHOOK_PRESETS.items())
+
+
+def get_preset_events(preset_id: str) -> List[str]:
+    """Get list of event class names for a preset.
+
+    Args:
+        preset_id: Preset identifier
+
+    Returns:
+        List of fully qualified event class names
+    """
+    preset = get_preset(preset_id)
+    if not preset:
+        return []
+    return [event_config["event"] for event_config in preset["events"]]
+
+
+def filter_presets_by_installed_apps(
+    installed_apps: list[str],
+) -> List[tuple[str, WebhookPreset]]:
+    """Filter webhook presets to only show those for installed apps.
+
+    Args:
+        installed_apps: List of installed app names (e.g., ["notes", "calendar", "forms"])
+
+    Returns:
+        List of (preset_id, preset_config) tuples for presets whose apps are installed
+    """
+    filtered = []
+    for preset_id, preset in WEBHOOK_PRESETS.items():
+        app_name = preset["app"]
+        # "files" is always available (core functionality)
+        if app_name == "files" or app_name in installed_apps:
+            filtered.append((preset_id, preset))
+    return filtered
@@ -15,6 +15,12 @@ from qdrant_client.models import FieldCondition, Filter, MatchValue, PointStruct
 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import get_settings
 from nextcloud_mcp_server.embedding import get_embedding_service
+from nextcloud_mcp_server.observability.metrics import (
+    record_qdrant_operation,
+    record_vector_sync_processing,
+    update_vector_sync_queue_size,
+)
+from nextcloud_mcp_server.observability.tracing import trace_operation
 from nextcloud_mcp_server.vector.document_chunker import DocumentChunker
 from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
 from nextcloud_mcp_server.vector.scanner import DocumentTask
@@ -56,11 +62,21 @@ async def processor_task(
            with anyio.fail_after(1.0):
                doc_task = await receive_stream.receive()

+            # Update queue size metric after receiving
+            stream_stats = receive_stream.statistics()
+            update_vector_sync_queue_size(stream_stats.current_buffer_used)
+
            # Process document
            await process_document(doc_task, nc_client)

+            # Update queue size metric after processing
+            stream_stats = receive_stream.statistics()
+            update_vector_sync_queue_size(stream_stats.current_buffer_used)
+
        except TimeoutError:
-            # No documents available, continue
+            # No documents available, update metric to show empty queue
+            stream_stats = receive_stream.statistics()
+            update_vector_sync_queue_size(stream_stats.current_buffer_used)
            continue

        except anyio.EndOfStream:
@@ -89,63 +105,96 @@ async def process_document(doc_task: DocumentTask, nc_client: NextcloudClient):
        doc_task: Document task to process
        nc_client: Authenticated Nextcloud client
    """
+    start_time = time.time()
+
    logger.debug(
        f"Processing {doc_task.doc_type}_{doc_task.doc_id} "
        f"for {doc_task.user_id} ({doc_task.operation})"
    )

-    qdrant_client = await get_qdrant_client()
-    settings = get_settings()
-
-    # Handle deletion
-    if doc_task.operation == "delete":
-        await qdrant_client.delete(
-            collection_name=settings.get_collection_name(),
-            points_selector=Filter(
-                must=[
-                    FieldCondition(
-                        key="user_id",
-                        match=MatchValue(value=doc_task.user_id),
-                    ),
-                    FieldCondition(
-                        key="doc_id",
-                        match=MatchValue(value=doc_task.doc_id),
-                    ),
-                    FieldCondition(
-                        key="doc_type",
-                        match=MatchValue(value=doc_task.doc_type),
-                    ),
-                ]
-            ),
-        )
-        logger.info(
-            f"Deleted {doc_task.doc_type}_{doc_task.doc_id} for {doc_task.user_id}"
-        )
-        return
-
-    # Handle indexing with retry
-    max_retries = 3
-    retry_delay = 1.0
-
-    for attempt in range(max_retries):
+    with trace_operation(
+        "vector_sync.process_document",
+        attributes={
+            "vector_sync.operation": "process",
+            "vector_sync.user_id": doc_task.user_id,
+            "vector_sync.doc_id": doc_task.doc_id,
+            "vector_sync.doc_type": doc_task.doc_type,
+            "vector_sync.doc_operation": doc_task.operation,
+        },
+    ):
        try:
-            await _index_document(doc_task, nc_client, qdrant_client)
-            return  # Success
+            qdrant_client = await get_qdrant_client()
+            settings = get_settings()

-        except (HTTPStatusError, Exception) as e:
-            if attempt < max_retries - 1:
-                logger.warning(
-                    f"Retry {attempt + 1}/{max_retries} for "
-                    f"{doc_task.doc_type}_{doc_task.doc_id}: {e}"
+            # Handle deletion
+            if doc_task.operation == "delete":
+                await qdrant_client.delete(
+                    collection_name=settings.get_collection_name(),
+                    points_selector=Filter(
+                        must=[
+                            FieldCondition(
+                                key="user_id",
+                                match=MatchValue(value=doc_task.user_id),
+                            ),
+                            FieldCondition(
+                                key="doc_id",
+                                match=MatchValue(value=doc_task.doc_id),
+                            ),
+                            FieldCondition(
+                                key="doc_type",
+                                match=MatchValue(value=doc_task.doc_type),
+                            ),
+                        ]
+                    ),
                )
-                await anyio.sleep(retry_delay)
-                retry_delay *= 2  # Exponential backoff
-            else:
-                logger.error(
-                    f"Failed to index {doc_task.doc_type}_{doc_task.doc_id} "
-                    f"after {max_retries} retries: {e}"
+                logger.info(
+                    f"Deleted {doc_task.doc_type}_{doc_task.doc_id} for {doc_task.user_id}"
                )
-                raise
+
+                # Record successful deletion metrics
+                duration = time.time() - start_time
+                record_qdrant_operation("delete", "success")
+                record_vector_sync_processing(duration, "success")
+                return
+
+            # Handle indexing with retry
+            max_retries = 3
+            retry_delay = 1.0
+
+            for attempt in range(max_retries):
+                try:
+                    await _index_document(doc_task, nc_client, qdrant_client)
+
+                    # Record successful processing metrics
+                    duration = time.time() - start_time
+                    record_qdrant_operation("upsert", "success")
+                    record_vector_sync_processing(duration, "success")
+                    return  # Success
+
+                except (HTTPStatusError, Exception) as e:
+                    if attempt < max_retries - 1:
+                        logger.warning(
+                            f"Retry {attempt + 1}/{max_retries} for "
+                            f"{doc_task.doc_type}_{doc_task.doc_id}: {e}"
+                        )
+                        await anyio.sleep(retry_delay)
+                        retry_delay *= 2  # Exponential backoff
+                    else:
+                        logger.error(
+                            f"Failed to index {doc_task.doc_type}_{doc_task.doc_id} "
+                            f"after {max_retries} retries: {e}"
+                        )
+                        # Record failed processing metrics
+                        duration = time.time() - start_time
+                        record_qdrant_operation("upsert", "error")
+                        record_vector_sync_processing(duration, "error")
+                        raise
+
+        except Exception:
+            # Catch any other unexpected errors
+            duration = time.time() - start_time
+            record_vector_sync_processing(duration, "error")
+            raise


 async def _index_document(
@@ -66,10 +66,23 @@ async def get_qdrant_client() -> AsyncQdrantClient:
        from nextcloud_mcp_server.embedding import get_embedding_service

        embedding_service = get_embedding_service()
+
+        # Detect dimension dynamically (for OllamaEmbeddingProvider)
+        if hasattr(embedding_service.provider, "_detect_dimension"):
+            await embedding_service.provider._detect_dimension()  # type: ignore[call-non-callable]
+
        expected_dimension = embedding_service.get_dimension()

-        try:
-            # Get existing collection
+        # Explicitly check if collection exists
+        logger.debug(f"Checking if collection '{collection_name}' exists...")
+        collections = await _qdrant_client.get_collections()
+        collection_names = [c.name for c in collections.collections]
+
+        if collection_name in collection_names:
+            # Collection exists - validate dimensions
+            logger.debug(
+                f"Collection '{collection_name}' found, validating dimensions..."
+            )
            collection_info = await _qdrant_client.get_collection(collection_name)
            actual_dimension = collection_info.config.params.vectors.size

@@ -91,12 +104,12 @@ async def get_qdrant_client() -> AsyncQdrantClient:
                f"(dimension={actual_dimension}, model={settings.ollama_embedding_model})"
            )

-        except Exception as e:
-            # Check if it's a dimension mismatch error (re-raise it)
-            if isinstance(e, ValueError) and "Dimension mismatch" in str(e):
-                raise
-
-            # Collection doesn't exist or other error, create it
+        else:
+            # Collection doesn't exist - create it
+            logger.info(
+                f"Collection '{collection_name}' not found, creating with "
+                f"dimension={expected_dimension}, model={settings.ollama_embedding_model}..."
+            )
            await _qdrant_client.create_collection(
                collection_name=collection_name,
                vectors_config=VectorParams(
@@ -13,6 +13,8 @@ from qdrant_client.models import FieldCondition, Filter, MatchValue

 from nextcloud_mcp_server.client import NextcloudClient
 from nextcloud_mcp_server.config import get_settings
+from nextcloud_mcp_server.observability.metrics import record_vector_sync_scan
+from nextcloud_mcp_server.observability.tracing import trace_operation
 from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client

 logger = logging.getLogger(__name__)
@@ -34,6 +36,57 @@ class DocumentTask:
 _potentially_deleted: dict[tuple[str, str], float] = {}


+async def get_last_indexed_timestamp(user_id: str) -> int | None:
+    """Get the most recent indexed_at timestamp for user's notes in Qdrant.
+
+    This timestamp can be used as pruneBefore parameter to optimize data transfer
+    when fetching notes - only notes modified after this timestamp will be sent
+    with full data.
+
+    Args:
+        user_id: User to query
+
+    Returns:
+        Unix timestamp of most recently indexed note, or None if no notes indexed yet
+    """
+    try:
+        qdrant_client = await get_qdrant_client()
+
+        # Query for user's notes, ordered by indexed_at descending, limit 1
+        scroll_result = await qdrant_client.scroll(
+            collection_name=get_settings().get_collection_name(),
+            scroll_filter=Filter(
+                must=[
+                    FieldCondition(key="user_id", match=MatchValue(value=user_id)),
+                    FieldCondition(key="doc_type", match=MatchValue(value="note")),
+                ]
+            ),
+            with_payload=["indexed_at"],
+            with_vectors=False,
+            limit=10000,  # Get all to find max
+        )
+
+        # Find max indexed_at across all results
+        num_points = len(scroll_result[0]) if scroll_result[0] else 0
+        logger.info(f"Found {num_points} indexed notes in Qdrant for user {user_id}")
+
+        if scroll_result[0]:
+            timestamps = [
+                point.payload.get("indexed_at", 0) for point in scroll_result[0]
+            ]
+            max_timestamp = max(timestamps)
+            logger.info(
+                f"Max indexed_at: {max_timestamp}, timestamps sample: {timestamps[:3]}"
+            )
+            return int(max_timestamp) if max_timestamp > 0 else None
+
+        logger.info(f"No indexed notes found for user {user_id}")
+        return None
+    except Exception as e:
+        logger.warning(f"Failed to get last indexed timestamp: {e}", exc_info=True)
+        return None
+
+
 async def scanner_task(
    send_stream: MemoryObjectSendStream[DocumentTask],
    shutdown_event: anyio.Event,
@@ -96,138 +149,158 @@ async def scan_user_documents(
        nc_client: Authenticated Nextcloud client
        initial_sync: If True, send all documents (first-time sync)
    """
-    logger.debug(f"Scanning documents for user: {user_id}")
+    import random

-    # Fetch all notes from Nextcloud
-    notes = [note async for note in nc_client.notes.get_all_notes()]
-    logger.debug(f"Found {len(notes)} notes for {user_id}")
-
-    if initial_sync:
-        # Send everything on first sync
-        for note in notes:
-            # Handle missing 'modified' field (use 0 as fallback)
-            modified_at = note.get("modified", 0)
-            if modified_at == 0:
-                logger.warning(
-                    f"Note {note['id']} missing 'modified' field, using 0 as fallback"
-                )
-
-            await send_stream.send(
-                DocumentTask(
-                    user_id=user_id,
-                    doc_id=str(note["id"]),
-                    doc_type="note",
-                    operation="index",
-                    modified_at=modified_at,
-                )
-            )
-        logger.info(f"Sent {len(notes)} documents for initial sync: {user_id}")
-        return
-
-    # Get indexed state from Qdrant
-    qdrant_client = await get_qdrant_client()
-    scroll_result = await qdrant_client.scroll(
-        collection_name=get_settings().get_collection_name(),
-        scroll_filter=Filter(
-            must=[
-                FieldCondition(key="user_id", match=MatchValue(value=user_id)),
-                FieldCondition(key="doc_type", match=MatchValue(value="note")),
-            ]
-        ),
-        with_payload=["doc_id", "indexed_at"],
-        with_vectors=False,
-        limit=10000,
+    scan_id = random.randint(1000, 9999)
+    logger.info(
+        f"[SCAN-{scan_id}] Starting scan for user: {user_id}, initial_sync={initial_sync}"
    )

-    indexed_docs = {
-        point.payload["doc_id"]: point.payload["indexed_at"]
-        for point in scroll_result[0]
-    }
-
-    logger.debug(f"Found {len(indexed_docs)} indexed documents in Qdrant")
-
-    # Compare and queue changes
-    queued = 0
-    nextcloud_doc_ids = {str(note["id"]) for note in notes}
-
-    for note in notes:
-        doc_id = str(note["id"])
-        indexed_at = indexed_docs.get(doc_id)
-
-        # Handle missing 'modified' field (use 0 as fallback)
-        modified_at = note.get("modified", 0)
-        if modified_at == 0:
-            logger.warning(
-                f"Note {doc_id} missing 'modified' field, using 0 as fallback"
+    with trace_operation(
+        "vector_sync.scan_user_documents",
+        attributes={
+            "vector_sync.operation": "scan",
+            "vector_sync.user_id": user_id,
+            "vector_sync.initial_sync": initial_sync,
+            "vector_sync.scan_id": scan_id,
+        },
+    ):
+        # Calculate prune timestamp for optimized data transfer
+        # Only notes modified after this will be sent with full data
+        prune_before = (
+            None if initial_sync else await get_last_indexed_timestamp(user_id)
+        )
+        if prune_before:
+            logger.info(
+                f"[SCAN-{scan_id}] Using pruneBefore={prune_before} to optimize data transfer"
            )

-        # If document reappeared, remove from potentially_deleted
-        doc_key = (user_id, doc_id)
-        if doc_key in _potentially_deleted:
-            logger.debug(
-                f"Document {doc_id} reappeared, removing from deletion grace period"
-            )
-            del _potentially_deleted[doc_key]
+        # Fetch all notes from Nextcloud
+        notes = [
+            note
+            async for note in nc_client.notes.get_all_notes(prune_before=prune_before)
+        ]
+        logger.info(f"[SCAN-{scan_id}] Found {len(notes)} notes for {user_id}")

-        # Send if never indexed or modified since last index
-        if indexed_at is None or modified_at > indexed_at:
-            await send_stream.send(
-                DocumentTask(
-                    user_id=user_id,
-                    doc_id=doc_id,
-                    doc_type="note",
-                    operation="index",
-                    modified_at=modified_at,
+        # Record documents scanned
+        record_vector_sync_scan(len(notes))
+
+        if initial_sync:
+            # Send everything on first sync
+            for note in notes:
+                modified_at = note.get("modified", 0)
+                await send_stream.send(
+                    DocumentTask(
+                        user_id=user_id,
+                        doc_id=str(note["id"]),
+                        doc_type="note",
+                        operation="index",
+                        modified_at=modified_at,
+                    )
                )
-            )
-            queued += 1
+            logger.info(f"Sent {len(notes)} documents for initial sync: {user_id}")
+            return

-    # Check for deleted documents (in Qdrant but not in Nextcloud)
-    # Use grace period: only delete after 2 consecutive scans confirm absence
-    settings = get_settings()
-    grace_period = settings.vector_sync_scan_interval * 1.5  # Allow 1.5 scan intervals
-    current_time = time.time()
+        # Get indexed state from Qdrant
+        qdrant_client = await get_qdrant_client()
+        scroll_result = await qdrant_client.scroll(
+            collection_name=get_settings().get_collection_name(),
+            scroll_filter=Filter(
+                must=[
+                    FieldCondition(key="user_id", match=MatchValue(value=user_id)),
+                    FieldCondition(key="doc_type", match=MatchValue(value="note")),
+                ]
+            ),
+            with_payload=["doc_id", "indexed_at"],
+            with_vectors=False,
+            limit=10000,
+        )

-    for doc_id in indexed_docs:
-        if doc_id not in nextcloud_doc_ids:
+        indexed_docs = {
+            point.payload["doc_id"]: point.payload["indexed_at"]
+            for point in scroll_result[0]
+        }
+
+        logger.debug(f"Found {len(indexed_docs)} indexed documents in Qdrant")
+
+        # Compare and queue changes
+        queued = 0
+        nextcloud_doc_ids = {str(note["id"]) for note in notes}
+
+        for note in notes:
+            doc_id = str(note["id"])
+            indexed_at = indexed_docs.get(doc_id)
+            modified_at = note.get("modified", 0)
+
+            # If document reappeared, remove from potentially_deleted
            doc_key = (user_id, doc_id)
-
            if doc_key in _potentially_deleted:
-                # Already marked as potentially deleted, check if grace period elapsed
-                first_missing_time = _potentially_deleted[doc_key]
-                time_missing = current_time - first_missing_time
-
-                if time_missing >= grace_period:
-                    # Grace period elapsed, send for deletion
-                    logger.info(
-                        f"Document {doc_id} missing for {time_missing:.1f}s "
-                        f"(>{grace_period:.1f}s grace period), sending deletion"
-                    )
-                    await send_stream.send(
-                        DocumentTask(
-                            user_id=user_id,
-                            doc_id=doc_id,
-                            doc_type="note",
-                            operation="delete",
-                            modified_at=0,
-                        )
-                    )
-                    queued += 1
-                    # Remove from tracking after sending deletion
-                    del _potentially_deleted[doc_key]
-                else:
-                    logger.debug(
-                        f"Document {doc_id} still missing "
-                        f"({time_missing:.1f}s/{grace_period:.1f}s grace period)"
-                    )
-            else:
-                # First time missing, add to grace period tracking
                logger.debug(
-                    f"Document {doc_id} missing for first time, starting grace period"
+                    f"Document {doc_id} reappeared, removing from deletion grace period"
                )
-                _potentially_deleted[doc_key] = current_time
+                del _potentially_deleted[doc_key]

-    if queued > 0:
-        logger.info(f"Sent {queued} documents for incremental sync: {user_id}")
-    else:
-        logger.debug(f"No changes detected for {user_id}")
+            # Send if never indexed or modified since last index
+            if indexed_at is None or modified_at > indexed_at:
+                await send_stream.send(
+                    DocumentTask(
+                        user_id=user_id,
+                        doc_id=doc_id,
+                        doc_type="note",
+                        operation="index",
+                        modified_at=modified_at,
+                    )
+                )
+                queued += 1
+
+        # Check for deleted documents (in Qdrant but not in Nextcloud)
+        # Use grace period: only delete after 2 consecutive scans confirm absence
+        settings = get_settings()
+        grace_period = (
+            settings.vector_sync_scan_interval * 1.5
+        )  # Allow 1.5 scan intervals
+        current_time = time.time()
+
+        for doc_id in indexed_docs:
+            if doc_id not in nextcloud_doc_ids:
+                doc_key = (user_id, doc_id)
+
+                if doc_key in _potentially_deleted:
+                    # Already marked as potentially deleted, check if grace period elapsed
+                    first_missing_time = _potentially_deleted[doc_key]
+                    time_missing = current_time - first_missing_time
+
+                    if time_missing >= grace_period:
+                        # Grace period elapsed, send for deletion
+                        logger.info(
+                            f"Document {doc_id} missing for {time_missing:.1f}s "
+                            f"(>{grace_period:.1f}s grace period), sending deletion"
+                        )
+                        await send_stream.send(
+                            DocumentTask(
+                                user_id=user_id,
+                                doc_id=doc_id,
+                                doc_type="note",
+                                operation="delete",
+                                modified_at=0,
+                            )
+                        )
+                        queued += 1
+                        # Remove from tracking after sending deletion
+                        del _potentially_deleted[doc_key]
+                    else:
+                        logger.debug(
+                            f"Document {doc_id} still missing "
+                            f"({time_missing:.1f}s/{grace_period:.1f}s grace period)"
+                        )
+                else:
+                    # First time missing, add to grace period tracking
+                    logger.debug(
+                        f"Document {doc_id} missing for first time, starting grace period"
+                    )
+                    _potentially_deleted[doc_key] = current_time
+
+        if queued > 0:
+            logger.info(f"Sent {queued} documents for incremental sync: {user_id}")
+        else:
+            logger.debug(f"No changes detected for {user_id}")
@@ -1,6 +1,6 @@
 [project]
 name = "nextcloud-mcp-server"
-version = "0.29.1"
+version = "0.33.1"
 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"}
@@ -23,14 +23,14 @@ dependencies = [
    "authlib>=1.6.5",
    "qdrant-client>=1.7.0",
    # Observability dependencies
-    "prometheus-client>=0.21.0",  # Prometheus metrics
-    "opentelemetry-api>=1.28.2",  # OpenTelemetry API
-    "opentelemetry-sdk>=1.28.2",  # OpenTelemetry SDK
-    "opentelemetry-instrumentation-asgi>=0.49b2",  # Auto-instrument ASGI/Starlette
-    "opentelemetry-instrumentation-httpx>=0.49b2",  # Auto-instrument httpx client
-    "opentelemetry-instrumentation-logging>=0.49b2",  # Logging integration
-    "opentelemetry-exporter-otlp-proto-grpc>=1.28.2",  # OTLP gRPC exporter
-    "python-json-logger>=3.2.0",  # Structured JSON logging
+    "prometheus-client>=0.21.0", # Prometheus metrics
+    "opentelemetry-api>=1.28.2", # OpenTelemetry API
+    "opentelemetry-sdk>=1.28.2", # OpenTelemetry SDK
+    "opentelemetry-instrumentation-asgi>=0.49b2", # Auto-instrument ASGI/Starlette
+    "opentelemetry-instrumentation-httpx>=0.49b2", # Auto-instrument httpx client
+    "opentelemetry-instrumentation-logging>=0.49b2", # Logging integration
+    "opentelemetry-exporter-otlp-proto-grpc>=1.28.2", # OTLP gRPC exporter
+    "python-json-logger>=3.2.0", # Structured JSON logging
 ]
 classifiers = [
    "Development Status :: 4 - Beta",
@@ -116,7 +116,7 @@ dev = [
 ]

 [project.scripts]
-nextcloud-mcp-server = "nextcloud_mcp_server.app:run"
+nextcloud-mcp-server = "nextcloud_mcp_server.cli:run"

 [[tool.uv.index]]
 name = "testpypi"
@@ -1,307 +0,0 @@
-#!/usr/bin/env python3
-"""Script to automatically add @require_scopes decorators to MCP tools.
-
-This script parses server module files and adds appropriate scope decorators
-based on the operation type (read vs write).
-
-Usage:
-    python scripts/add_scope_decorators.py [--dry-run] [--file FILE]
-"""
-
-import argparse
-import ast
-import re
-from pathlib import Path
-from typing import List, Tuple
-
-# Operation patterns for classification
-READ_PATTERNS = [
-    r".*_get_.*",
-    r".*_get$",
-    r".*_list_.*",
-    r".*_list$",
-    r".*_search_.*",
-    r".*_search$",
-    r".*_read_.*",
-    r".*_read$",
-    r".*_find_.*",
-    r".*_find$",
-    r".*_fetch_.*",
-    r".*_fetch$",
-    r".*_retrieve_.*",
-    r".*_retrieve$",
-]
-
-WRITE_PATTERNS = [
-    r".*_create_.*",
-    r".*_create$",
-    r".*_update_.*",
-    r".*_update$",
-    r".*_delete_.*",
-    r".*_delete$",
-    r".*_append_.*",
-    r".*_append$",
-    r".*_modify_.*",
-    r".*_modify$",
-    r".*_set_.*",
-    r".*_set$",
-    r".*_add_.*",
-    r".*_add$",
-    r".*_remove_.*",
-    r".*_remove$",
-    r".*_edit_.*",
-    r".*_edit$",
-    r".*_move_.*",
-    r".*_move$",
-    r".*_copy_.*",
-    r".*_copy$",
-    r".*_upload_.*",
-    r".*_upload$",
-    r".*_download_.*",
-    r".*_download$",
-    r".*_share_.*",
-    r".*_share$",
-    r".*_unshare_.*",
-    r".*_unshare$",
-    r".*_bulk_.*",  # Bulk operations are typically writes
-]
-
-
-def classify_operation(func_name: str) -> str | None:
-    """Classify a function as read or write operation.
-
-    Args:
-        func_name: Function name to classify
-
-    Returns:
-        "nc:read", "nc:write", or None if cannot classify
-    """
-    # Check write patterns first (more specific)
-    for pattern in WRITE_PATTERNS:
-        if re.match(pattern, func_name):
-            return "nc:write"
-
-    # Check read patterns
-    for pattern in READ_PATTERNS:
-        if re.match(pattern, func_name):
-            return "nc:read"
-
-    return None
-
-
-def has_scope_decorator(decorators: List[ast.expr]) -> bool:
-    """Check if function already has @require_scopes decorator."""
-    for decorator in decorators:
-        if isinstance(decorator, ast.Call):
-            if (
-                isinstance(decorator.func, ast.Name)
-                and decorator.func.id == "require_scopes"
-            ):
-                return True
-        elif isinstance(decorator, ast.Name) and decorator.name == "require_scopes":
-            return True
-    return False
-
-
-def has_mcp_tool_decorator(decorators: List[ast.expr]) -> bool:
-    """Check if function has @mcp.tool() decorator."""
-    for decorator in decorators:
-        if isinstance(decorator, ast.Call):
-            if isinstance(decorator.func, ast.Attribute):
-                if decorator.func.attr == "tool":
-                    return True
-    return False
-
-
-def find_tools_needing_decorators(
-    file_path: Path, verbose: bool = False
-) -> List[Tuple[str, int, str]]:
-    """Find all tools that need scope decorators.
-
-    Returns:
-        List of (function_name, line_number, required_scope)
-    """
-    with open(file_path) as f:
-        content = f.read()
-
-    try:
-        tree = ast.parse(content)
-    except SyntaxError as e:
-        print(f"  ⚠️  Syntax error in {file_path}: {e}")
-        return []
-
-    tools_to_update = []
-    total_functions = 0
-    mcp_tools = 0
-    already_has_scope = 0
-    cannot_classify = 0
-
-    for node in ast.walk(tree):
-        if isinstance(node, ast.FunctionDef):
-            total_functions += 1
-
-            if verbose and node.decorator_list:
-                decorators_str = [
-                    ast.unparse(d) if hasattr(ast, "unparse") else str(d)
-                    for d in node.decorator_list
-                ]
-                print(f"  Function {node.name} has decorators: {decorators_str}")
-
-            # Check if it's an MCP tool
-            if not has_mcp_tool_decorator(node.decorator_list):
-                continue
-
-            mcp_tools += 1
-
-            # Check if it already has scope decorator
-            if has_scope_decorator(node.decorator_list):
-                already_has_scope += 1
-                continue
-
-            # Classify operation
-            scope = classify_operation(node.name)
-            if scope:
-                tools_to_update.append((node.name, node.lineno, scope))
-            else:
-                cannot_classify += 1
-                if verbose:
-                    print(f"  ⚠️  Cannot classify: {node.name}")
-
-    if verbose:
-        print(
-            f"  Debug: total_functions={total_functions}, mcp_tools={mcp_tools}, already_has_scope={already_has_scope}, cannot_classify={cannot_classify}"
-        )
-
-    return tools_to_update
-
-
-def add_decorator_to_file(
-    file_path: Path, dry_run: bool = False, verbose: bool = False
-) -> int:
-    """Add @require_scopes decorators to tools in a file.
-
-    Returns:
-        Number of decorators added
-    """
-    tools = find_tools_needing_decorators(file_path, verbose=verbose)
-
-    if not tools:
-        return 0
-
-    print(f"\n📝 {file_path.relative_to(Path.cwd())}")
-
-    with open(file_path) as f:
-        lines = f.readlines()
-
-    # Check if require_scopes is already imported
-    has_import = False
-    import_line_idx = None
-    for i, line in enumerate(lines):
-        if "from nextcloud_mcp_server.auth import" in line and "require_scopes" in line:
-            has_import = True
-            break
-        elif "from nextcloud_mcp_server.auth import" in line:
-            import_line_idx = i
-
-    # Add import if needed
-    if not has_import:
-        if import_line_idx is not None:
-            # Add require_scopes to existing import
-            old_line = lines[import_line_idx]
-            if "(" in old_line:
-                # Multi-line import
-                print(
-                    "  ⚠️  Multi-line import detected, please add manually: from nextcloud_mcp_server.auth import require_scopes"
-                )
-            else:
-                # Single line import - add require_scopes
-                lines[import_line_idx] = (
-                    old_line.rstrip().rstrip(")").rstrip() + ", require_scopes)\n"
-                )
-                print("  ✓ Added require_scopes to import")
-        else:
-            # No auth import exists, add new import
-            # Find first import line
-            for i, line in enumerate(lines):
-                if line.startswith("from nextcloud_mcp_server"):
-                    lines.insert(
-                        i, "from nextcloud_mcp_server.auth import require_scopes\n"
-                    )
-                    print(
-                        "  ✓ Added import: from nextcloud_mcp_server.auth import require_scopes"
-                    )
-                    break
-
-    # Add decorators to tools (in reverse order to preserve line numbers)
-    for func_name, line_num, scope in reversed(tools):
-        # Find the @mcp.tool() decorator line
-        for i in range(line_num - 1, max(0, line_num - 10), -1):
-            if "@mcp.tool()" in lines[i]:
-                # Get indentation from @mcp.tool() line
-                indent = len(lines[i]) - len(lines[i].lstrip())
-                decorator_line = " " * indent + f'@require_scopes("{scope}")\n'
-                lines.insert(i + 1, decorator_line)
-                print(f'  ✓ {func_name}:{line_num} → @require_scopes("{scope}")')
-                break
-
-    if not dry_run:
-        with open(file_path, "w") as f:
-            f.writelines(lines)
-        print("  💾 Saved changes")
-    else:
-        print("  🔍 DRY RUN - no changes written")
-
-    return len(tools)
-
-
-def main():
-    parser = argparse.ArgumentParser(
-        description="Add @require_scopes decorators to MCP tools"
-    )
-    parser.add_argument(
-        "--dry-run",
-        action="store_true",
-        help="Show what would be changed without modifying files",
-    )
-    parser.add_argument(
-        "--file",
-        type=Path,
-        help="Process a single file instead of all server modules",
-    )
-    parser.add_argument(
-        "--verbose",
-        "-v",
-        action="store_true",
-        help="Show debug information",
-    )
-    args = parser.parse_args()
-
-    server_dir = Path(__file__).parent.parent / "nextcloud_mcp_server" / "server"
-
-    if args.file:
-        files = [args.file]
-    else:
-        files = sorted(server_dir.glob("*.py"))
-        files = [f for f in files if f.name != "__init__.py"]
-
-    print("🔍 Scanning for tools needing scope decorators...")
-    print(
-        f"   {'DRY RUN MODE - No changes will be made' if args.dry_run else 'LIVE MODE - Files will be modified'}"
-    )
-
-    total_added = 0
-    for file_path in files:
-        added = add_decorator_to_file(
-            file_path, dry_run=args.dry_run, verbose=args.verbose
-        )
-        total_added += added
-
-    print(f"\n{'📊 Summary (dry run)' if args.dry_run else '✅ Complete'}")
-    print(f"   Total decorators added: {total_added}")
-
-    if args.dry_run:
-        print("\n💡 Run without --dry-run to apply changes")
-
-
-if __name__ == "__main__":
-    main()
@@ -1,232 +0,0 @@
-#!/usr/bin/env python3
-"""Simpler script to add @require_scopes decorators using regex.
-
-This script uses regex patterns to find @mcp.tool() decorators and adds
-the appropriate @require_scopes decorator based on function name patterns.
-
-Usage:
-    python scripts/add_scope_decorators_simple.py [--dry-run]
-"""
-
-import argparse
-import re
-from pathlib import Path
-
-# Operation patterns for classification
-READ_KEYWORDS = [
-    "get",
-    "list",
-    "search",
-    "read",
-    "find",
-    "fetch",
-    "retrieve",
-    "upcoming",
-]
-WRITE_KEYWORDS = [
-    "create",
-    "update",
-    "delete",
-    "append",
-    "modify",
-    "set",
-    "add",
-    "remove",
-    "edit",
-    "move",
-    "copy",
-    "upload",
-    "download",
-    "share",
-    "unshare",
-    "bulk",
-    "manage",
-    "import",
-    "reindex",
-    "archive",
-    "unarchive",
-    "reorder",
-    "assign",
-    "unassign",
-    "insert",
-    "write",
-]
-
-
-def classify_function(func_name: str) -> str | None:
-    """Classify a function name as read or write operation."""
-    func_lower = func_name.lower()
-
-    # Check write keywords first (more specific)
-    for keyword in WRITE_KEYWORDS:
-        if f"_{keyword}_" in func_lower or func_lower.endswith(f"_{keyword}"):
-            return "nc:write"
-
-    # Check read keywords
-    for keyword in READ_KEYWORDS:
-        if f"_{keyword}_" in func_lower or func_lower.endswith(f"_{keyword}"):
-            return "nc:read"
-
-    return None
-
-
-def process_file(file_path: Path, dry_run: bool = False) -> int:
-    """Process a single file to add @require_scopes decorators.
-
-    Returns:
-        Number of decorators added
-    """
-    with open(file_path) as f:
-        lines = f.readlines()
-
-    # Check if require_scopes is already imported
-    has_import = False
-    import_line_idx = None
-
-    for i, line in enumerate(lines):
-        if "from nextcloud_mcp_server.auth import" in line:
-            if "require_scopes" in line:
-                has_import = True
-            else:
-                import_line_idx = i
-
-    modified = False
-    decorators_added = 0
-
-    # Find all @mcp.tool() decorators
-    i = 0
-    while i < len(lines):
-        line = lines[i]
-
-        # Look for @mcp.tool() decorator
-        if re.match(r"\s*@mcp\.tool\(\)", line):
-            # Check if next line already has @require_scopes
-            if i + 1 < len(lines) and "@require_scopes" in lines[i + 1]:
-                i += 1
-                continue
-
-            # Find the function definition (should be on next line or after other decorators)
-            func_line_idx = i + 1
-            while func_line_idx < len(lines) and not lines[
-                func_line_idx
-            ].strip().startswith("async def"):
-                func_line_idx += 1
-
-            if func_line_idx >= len(lines):
-                i += 1
-                continue
-
-            # Extract function name
-            func_match = re.match(r"\s*async def (\w+)\(", lines[func_line_idx])
-            if not func_match:
-                i += 1
-                continue
-
-            func_name = func_match.group(1)
-            scope = classify_function(func_name)
-
-            if scope:
-                # Get indentation from @mcp.tool() line
-                indent = len(line) - len(line.lstrip())
-                decorator_line = " " * indent + f'@require_scopes("{scope}")\n'
-
-                # Insert after @mcp.tool()
-                lines.insert(i + 1, decorator_line)
-                decorators_added += 1
-                modified = True
-                print(f'  ✓ {func_name} → @require_scopes("{scope}")')
-            else:
-                print(f"  ⚠️  Cannot classify: {func_name}")
-
-        i += 1
-
-    # Add import if needed and decorators were added
-    if decorators_added > 0 and not has_import:
-        if import_line_idx is not None:
-            # Add to existing import
-            old_line = lines[import_line_idx]
-            if old_line.rstrip().endswith(")"):
-                lines[import_line_idx] = old_line.rstrip()[:-1] + ", require_scopes)\n"
-            else:
-                lines[import_line_idx] = old_line.rstrip() + ", require_scopes\n"
-            print("  ✓ Added require_scopes to existing import")
-            modified = True
-        else:
-            # No auth import exists, add new import after last 'from nextcloud_mcp_server' import
-            last_nc_import_idx = None
-            for i, line in enumerate(lines):
-                if line.startswith("from nextcloud_mcp_server"):
-                    last_nc_import_idx = i
-
-            if last_nc_import_idx is not None:
-                lines.insert(
-                    last_nc_import_idx + 1,
-                    "from nextcloud_mcp_server.auth import require_scopes\n",
-                )
-                print(
-                    "  ✓ Added new import: from nextcloud_mcp_server.auth import require_scopes"
-                )
-                modified = True
-            else:
-                print("  ⚠️  Could not find place to add require_scopes import")
-
-    # Write changes
-    if modified and not dry_run:
-        with open(file_path, "w") as f:
-            f.writelines(lines)
-        print(f"  💾 Saved changes to {file_path.name}")
-    elif dry_run and decorators_added > 0:
-        print(f"  🔍 DRY RUN - would add {decorators_added} decorators")
-
-    return decorators_added
-
-
-def main():
-    parser = argparse.ArgumentParser(
-        description="Add @require_scopes decorators to MCP tools"
-    )
-    parser.add_argument(
-        "--dry-run",
-        action="store_true",
-        help="Show what would be changed without modifying files",
-    )
-    parser.add_argument(
-        "--file",
-        type=Path,
-        help="Process a single file instead of all server modules",
-    )
-    args = parser.parse_args()
-
-    server_dir = Path(__file__).parent.parent / "nextcloud_mcp_server" / "server"
-
-    if args.file:
-        files = [args.file]
-    else:
-        files = sorted(server_dir.glob("*.py"))
-        files = [f for f in files if f.name != "__init__.py"]
-
-    print("🔍 Scanning for tools needing scope decorators...")
-    print(
-        f"   {'DRY RUN MODE - No changes will be made' if args.dry_run else 'LIVE MODE - Files will be modified'}"
-    )
-
-    total_added = 0
-    for file_path in files:
-        file_path = file_path.resolve()  # Convert to absolute path
-        try:
-            display_path = file_path.relative_to(Path.cwd())
-        except ValueError:
-            display_path = file_path.name
-        print(f"\n📝 {display_path}")
-        added = process_file(file_path, dry_run=args.dry_run)
-        total_added += added
-
-    print(f"\n{'📊 Summary (dry run)' if args.dry_run else '✅ Complete'}")
-    print(f"   Total decorators added: {total_added}")
-
-    if args.dry_run and total_added > 0:
-        print("\n💡 Run without --dry-run to apply changes")
-
-
-if __name__ == "__main__":
-    main()
@@ -1,90 +0,0 @@
-#!/bin/bash
-set -e
-
-echo "=== Testing Separate Clients Architecture ==="
-echo ""
-
-# Check both clients exist in Keycloak
-echo "1. Verifying Keycloak clients..."
-docker compose exec -T app curl -s http://keycloak:8080/realms/nextcloud-mcp/.well-known/openid-configuration > /dev/null && echo "✓ Keycloak realm available"
-
-# Check user_oidc provider configuration
-echo ""
-echo "2. Checking user_oidc provider..."
-PROVIDER_INFO=$(docker compose exec -T app php occ user_oidc:provider keycloak)
-echo "$PROVIDER_INFO" | grep -q "nextcloud" && echo "✓ user_oidc configured with 'nextcloud' client"
-
-# Get token from nextcloud-mcp-server client
-echo ""
-echo "3. Getting token from 'nextcloud-mcp-server' client..."
-TOKEN=$(curl -s -X POST "http://localhost:8888/realms/nextcloud-mcp/protocol/openid-connect/token" \
-  -d "grant_type=password" \
-  -d "client_id=nextcloud-mcp-server" \
-  -d "client_secret=mcp-secret-change-in-production" \
-  -d "username=admin" \
-  -d "password=admin" \
-  -d "scope=openid profile email offline_access" | jq -r '.access_token')
-
-if [ "$TOKEN" = "null" ] || [ -z "$TOKEN" ]; then
-    echo "✗ Failed to get token"
-    exit 1
-fi
-
-echo "✓ Got token from nextcloud-mcp-server client"
-
-# Check token claims
-echo ""
-echo "4. Inspecting token claims..."
-CLAIMS=$(echo "$TOKEN" | cut -d'.' -f2 | base64 -d 2>/dev/null | jq '{aud, azp, iss, preferred_username}')
-echo "$CLAIMS"
-
-AUD=$(echo "$CLAIMS" | jq -r '.aud')
-AZP=$(echo "$CLAIMS" | jq -r '.azp')
-
-echo ""
-echo "Architecture validation:"
-if [ "$AUD" = "nextcloud" ]; then
-    echo "  ✓ aud='nextcloud' - Token intended for Nextcloud resource server"
-else
-    echo "  ✗ FAILED: aud='$AUD', expected 'nextcloud'"
-    exit 1
-fi
-
-if [ "$AZP" = "nextcloud-mcp-server" ]; then
-    echo "  ✓ azp='nextcloud-mcp-server' - Token requested by MCP Server client"
-else
-    echo "  ✗ FAILED: azp='$AZP', expected 'nextcloud-mcp-server'"
-    exit 1
-fi
-
-# Test with Nextcloud API
-echo ""
-echo "5. Testing token with Nextcloud API..."
-HTTP_CODE=$(curl -s -w "%{http_code}" -o /tmp/nc_response.json \
-    -H "Authorization: Bearer $TOKEN" \
-    "http://localhost:8080/ocs/v2.php/cloud/capabilities?format=json")
-
-echo "HTTP Status: $HTTP_CODE"
-
-if [ "$HTTP_CODE" = "200" ]; then
-    echo "✓ Token validated successfully!"
-    echo ""
-    echo "===================================================================="
-    echo "SUCCESS: Separate Clients Architecture Working!"
-    echo "===================================================================="
-    echo ""
-    echo "Summary:"
-    echo "  - MCP Server client: 'nextcloud-mcp-server' (requests tokens)"
-    echo "  - Resource server: 'nextcloud' (validates tokens via user_oidc)"
-    echo "  - Token audience: 'nextcloud' (proper resource targeting)"
-    echo "  - Token azp: 'nextcloud-mcp-server' (identifies requester)"
-    echo ""
-    echo "This architecture supports:"
-    echo "  - Future multi-resource tokens: aud=['nextcloud', 'other-service']"
-    echo "  - Clear separation of OAuth client vs resource server"
-    echo "  - RFC 8707 Resource Indicators compliance"
-else
-    echo "✗ Token validation failed"
-    cat /tmp/nc_response.json
-    exit 1
-fi
@@ -0,0 +1,112 @@
+"""Unit tests for permission checking."""
+
+import pytest
+from httpx import AsyncClient
+
+from nextcloud_mcp_server.auth.permissions import is_nextcloud_admin
+from nextcloud_mcp_server.client.users import UsersClient
+
+
+@pytest.fixture
+def mock_request(mocker):
+    """Create a mock Starlette request."""
+    request = mocker.Mock()
+    request.user = mocker.Mock()
+    request.user.display_name = "testuser"
+    return request
+
+
+@pytest.fixture
+def mock_http_client(mocker):
+    """Create a mock HTTP client."""
+    return mocker.AsyncMock(spec=AsyncClient)
+
+
+@pytest.mark.unit
+async def test_is_nextcloud_admin_true(mock_request, mock_http_client, mocker):
+    """Test checking if user is admin (admin group membership)."""
+    # Mock the get_user_groups method to return admin group
+    mock_get_user_groups = mocker.patch.object(
+        UsersClient, "get_user_groups", return_value=["admin", "users"]
+    )
+
+    is_admin = await is_nextcloud_admin(mock_request, mock_http_client)
+
+    assert is_admin is True
+    mock_get_user_groups.assert_called_once_with("testuser")
+
+
+@pytest.mark.unit
+async def test_is_nextcloud_admin_false(mock_request, mock_http_client, mocker):
+    """Test checking if user is not admin (no admin group membership)."""
+    # Mock the get_user_groups method to return no admin group
+    mock_get_user_groups = mocker.patch.object(
+        UsersClient, "get_user_groups", return_value=["users", "editors"]
+    )
+
+    is_admin = await is_nextcloud_admin(mock_request, mock_http_client)
+
+    assert is_admin is False
+    mock_get_user_groups.assert_called_once_with("testuser")
+
+
+@pytest.mark.unit
+async def test_is_nextcloud_admin_empty_groups(mock_request, mock_http_client, mocker):
+    """Test checking admin status when user has no groups."""
+    # Mock the get_user_groups method to return empty list
+    mock_get_user_groups = mocker.patch.object(
+        UsersClient, "get_user_groups", return_value=[]
+    )
+
+    is_admin = await is_nextcloud_admin(mock_request, mock_http_client)
+
+    assert is_admin is False
+    mock_get_user_groups.assert_called_once_with("testuser")
+
+
+@pytest.mark.unit
+async def test_is_nextcloud_admin_no_username(mock_request, mock_http_client, mocker):
+    """Test checking admin status when username is missing."""
+    # Set username to None
+    mock_request.user.display_name = None
+
+    mock_get_user_groups = mocker.patch.object(UsersClient, "get_user_groups")
+
+    is_admin = await is_nextcloud_admin(mock_request, mock_http_client)
+
+    assert is_admin is False
+    # Ensure get_user_groups was not called
+    mock_get_user_groups.assert_not_called()
+
+
+@pytest.mark.unit
+async def test_is_nextcloud_admin_api_error(mock_request, mock_http_client, mocker):
+    """Test checking admin status when API call fails."""
+    # Mock the get_user_groups method to raise an exception
+    mock_get_user_groups = mocker.patch.object(
+        UsersClient,
+        "get_user_groups",
+        side_effect=Exception("API error"),
+    )
+
+    is_admin = await is_nextcloud_admin(mock_request, mock_http_client)
+
+    assert is_admin is False
+    mock_get_user_groups.assert_called_once_with("testuser")
+
+
+@pytest.mark.unit
+async def test_is_nextcloud_admin_case_sensitive(
+    mock_request, mock_http_client, mocker
+):
+    """Test that admin group check is case-sensitive."""
+    # Mock with "Admin" (capital A) instead of "admin"
+    mock_get_user_groups = mocker.patch.object(
+        UsersClient, "get_user_groups", return_value=["Admin", "users"]
+    )
+
+    is_admin = await is_nextcloud_admin(mock_request, mock_http_client)
+
+    # Should be False because Nextcloud uses lowercase "admin"
+    assert is_admin is False
+    mock_get_user_groups.assert_called_once_with("testuser")
@@ -239,23 +239,46 @@ async def test_attachments_category_change_handling(nc_client: NextcloudClient):
        assert retrieved_content1 == attachment_content
        logger.info("Attachment retrieved successfully from initial category.")

-        # 4. Update note category
+        # 4. Update note category (with retry for ETag conflicts from background scanner)
        logger.info(
            f"Updating note {note_id} category from '{initial_category}' to '{new_category}'"
        )
-        # Need to fetch the latest etag after attachment add (WebDAV ops don't update note etag)
-        current_note_data = await nc_client.notes.get_note(note_id=note_id)
-        current_etag = current_note_data["etag"]
-        updated_note = await nc_client.notes.update(
-            note_id=note_id,
-            etag=current_etag,
-            category=new_category,
-            title=note_title,
-            content="Updated content",  # Pass required fields
-        )
-        etag3 = updated_note["etag"]
-        assert updated_note["category"] == new_category
-        logger.info(f"Note category updated successfully. New Etag: {etag3}")
+        # Retry logic for 412 Precondition Failed (ETag conflict)
+        # This can happen if the background vector scanner touches the note
+        max_update_attempts = 3
+        for attempt in range(max_update_attempts):
+            try:
+                # Fetch the latest etag
+                current_note_data = await nc_client.notes.get_note(note_id=note_id)
+                current_etag = current_note_data["etag"]
+                logger.info(
+                    f"Update attempt {attempt + 1}/{max_update_attempts}, current etag: {current_etag}"
+                )
+
+                updated_note = await nc_client.notes.update(
+                    note_id=note_id,
+                    etag=current_etag,
+                    category=new_category,
+                    title=note_title,
+                    content="Updated content",  # Pass required fields
+                )
+                etag3 = updated_note["etag"]
+                assert updated_note["category"] == new_category
+                logger.info(f"Note category updated successfully. New Etag: {etag3}")
+                break  # Success, exit retry loop
+
+            except HTTPStatusError as e:
+                if e.response.status_code == 412 and attempt < max_update_attempts - 1:
+                    # ETag conflict (likely from background scanner), retry
+                    logger.warning(
+                        f"ETag conflict (412) on attempt {attempt + 1}, retrying..."
+                    )
+                    time.sleep(1)  # Brief delay before retry
+                    continue
+                else:
+                    # Not a 412 or out of retries, re-raise
+                    raise
+
        time.sleep(1)

        # 5. Verify attachment retrieval from *new* category (passing new category)
@@ -0,0 +1,218 @@
+"""Unit tests for WebhooksClient."""
+
+import pytest
+from httpx import AsyncClient
+
+from nextcloud_mcp_server.client.webhooks import WebhooksClient
+
+
+@pytest.fixture
+def webhooks_client(mocker):
+    """Create a WebhooksClient with mocked HTTP client."""
+    mock_http_client = mocker.AsyncMock(spec=AsyncClient)
+    return WebhooksClient(mock_http_client, "testuser")
+
+
+@pytest.mark.unit
+async def test_list_webhooks(webhooks_client, mocker):
+    """Test listing registered webhooks."""
+    mock_response = mocker.Mock()
+    mock_response.json.return_value = {
+        "ocs": {
+            "data": [
+                {
+                    "id": 1,
+                    "uri": "http://example.com/webhook",
+                    "event": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+                    "httpMethod": "POST",
+                },
+                {
+                    "id": 2,
+                    "uri": "http://example.com/webhook",
+                    "event": "OCP\\Files\\Events\\Node\\NodeWrittenEvent",
+                    "httpMethod": "POST",
+                },
+            ]
+        }
+    }
+
+    mock_make_request = mocker.patch.object(
+        WebhooksClient, "_make_request", return_value=mock_response
+    )
+
+    webhooks = await webhooks_client.list_webhooks()
+
+    assert len(webhooks) == 2
+    assert webhooks[0]["id"] == 1
+    assert webhooks[0]["event"] == "OCP\\Files\\Events\\Node\\NodeCreatedEvent"
+    assert webhooks[1]["id"] == 2
+
+    mock_make_request.assert_called_once_with(
+        "GET",
+        "/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks",
+        headers={"OCS-APIRequest": "true", "Accept": "application/json"},
+    )
+
+
+@pytest.mark.unit
+async def test_list_webhooks_empty(webhooks_client, mocker):
+    """Test listing webhooks when none are registered."""
+    mock_response = mocker.Mock()
+    mock_response.json.return_value = {"ocs": {"data": []}}
+
+    mocker.patch.object(WebhooksClient, "_make_request", return_value=mock_response)
+
+    webhooks = await webhooks_client.list_webhooks()
+
+    assert webhooks == []
+
+
+@pytest.mark.unit
+async def test_create_webhook(webhooks_client, mocker):
+    """Test creating a webhook registration."""
+    mock_response = mocker.Mock()
+    mock_response.json.return_value = {
+        "ocs": {
+            "data": {
+                "id": 123,
+                "uri": "http://example.com/webhook",
+                "event": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+                "httpMethod": "POST",
+                "authMethod": "none",
+            }
+        }
+    }
+
+    mock_make_request = mocker.patch.object(
+        WebhooksClient, "_make_request", return_value=mock_response
+    )
+
+    webhook_data = await webhooks_client.create_webhook(
+        event="OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+        uri="http://example.com/webhook",
+    )
+
+    assert webhook_data["id"] == 123
+    assert webhook_data["event"] == "OCP\\Files\\Events\\Node\\NodeCreatedEvent"
+
+    mock_make_request.assert_called_once()
+    call_args = mock_make_request.call_args
+    assert call_args[0][0] == "POST"
+    assert call_args[0][1] == "/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks"
+
+
+@pytest.mark.unit
+async def test_create_webhook_with_filter(webhooks_client, mocker):
+    """Test creating a webhook with event filter."""
+    mock_response = mocker.Mock()
+    mock_response.json.return_value = {
+        "ocs": {
+            "data": {
+                "id": 124,
+                "uri": "http://example.com/webhook",
+                "event": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+                "eventFilter": {"user.uid": "bob"},
+            }
+        }
+    }
+
+    mock_make_request = mocker.patch.object(
+        WebhooksClient, "_make_request", return_value=mock_response
+    )
+
+    webhook_data = await webhooks_client.create_webhook(
+        event="OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+        uri="http://example.com/webhook",
+        event_filter={"user.uid": "bob"},
+    )
+
+    assert webhook_data["id"] == 124
+    assert webhook_data["eventFilter"] == {"user.uid": "bob"}
+
+    mock_make_request.assert_called_once()
+    call_args = mock_make_request.call_args
+    assert call_args[1]["json"]["eventFilter"] == {"user.uid": "bob"}
+
+
+@pytest.mark.unit
+async def test_create_webhook_with_auth_headers(webhooks_client, mocker):
+    """Test creating a webhook with authentication headers."""
+    mock_response = mocker.Mock()
+    mock_response.json.return_value = {
+        "ocs": {
+            "data": {
+                "id": 125,
+                "uri": "http://example.com/webhook",
+                "event": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+                "authMethod": "bearer",
+            }
+        }
+    }
+
+    mock_make_request = mocker.patch.object(
+        WebhooksClient, "_make_request", return_value=mock_response
+    )
+
+    webhook_data = await webhooks_client.create_webhook(
+        event="OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+        uri="http://example.com/webhook",
+        auth_method="bearer",
+        headers={"Authorization": "Bearer secret-token"},
+    )
+
+    assert webhook_data["id"] == 125
+    assert webhook_data["authMethod"] == "bearer"
+
+    mock_make_request.assert_called_once()
+    call_args = mock_make_request.call_args
+    assert call_args[1]["json"]["authMethod"] == "bearer"
+    assert call_args[1]["json"]["headers"] == {"Authorization": "Bearer secret-token"}
+
+
+@pytest.mark.unit
+async def test_delete_webhook(webhooks_client, mocker):
+    """Test deleting a webhook registration."""
+    mock_response = mocker.Mock()
+
+    mock_make_request = mocker.patch.object(
+        WebhooksClient, "_make_request", return_value=mock_response
+    )
+
+    await webhooks_client.delete_webhook(webhook_id=123)
+
+    mock_make_request.assert_called_once_with(
+        "DELETE",
+        "/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks/123",
+        headers={"OCS-APIRequest": "true", "Accept": "application/json"},
+    )
+
+
+@pytest.mark.unit
+async def test_get_webhook(webhooks_client, mocker):
+    """Test getting a specific webhook by ID."""
+    mock_response = mocker.Mock()
+    mock_response.json.return_value = {
+        "ocs": {
+            "data": {
+                "id": 123,
+                "uri": "http://example.com/webhook",
+                "event": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+                "httpMethod": "POST",
+            }
+        }
+    }
+
+    mock_make_request = mocker.patch.object(
+        WebhooksClient, "_make_request", return_value=mock_response
+    )
+
+    webhook_data = await webhooks_client.get_webhook(webhook_id=123)
+
+    assert webhook_data["id"] == 123
+    assert webhook_data["event"] == "OCP\\Files\\Events\\Node\\NodeCreatedEvent"
+
+    mock_make_request.assert_called_once_with(
+        "GET",
+        "/ocs/v2.php/apps/webhook_listeners/api/v1/webhooks/123",
+        headers={"OCS-APIRequest": "true", "Accept": "application/json"},
+    )
@@ -0,0 +1,322 @@
+"""Integration tests for Qdrant collection auto-creation.
+
+These tests validate that:
+1. Collections are automatically created on first access
+2. Dimension validation detects mismatches
+3. Idempotent initialization (multiple calls don't fail)
+4. Proper error handling and logging
+"""
+
+from unittest.mock import Mock
+
+import pytest
+
+from nextcloud_mcp_server.vector.qdrant_client import get_qdrant_client
+
+pytestmark = pytest.mark.integration
+
+
+@pytest.fixture(autouse=True)
+async def reset_singleton():
+    """Reset the global Qdrant client singleton between tests."""
+    global _qdrant_client
+    import nextcloud_mcp_server.vector.qdrant_client as qdrant_module
+
+    # Store original
+    original = qdrant_module._qdrant_client
+
+    # Reset for test
+    qdrant_module._qdrant_client = None
+
+    yield
+
+    # Restore original
+    qdrant_module._qdrant_client = original
+
+
+@pytest.mark.integration
+async def test_collection_auto_created_on_first_access(monkeypatch):
+    """Test that collection is automatically created if it doesn't exist."""
+    # Mock settings
+    from nextcloud_mcp_server.config import Settings
+
+    mock_settings = Settings(
+        qdrant_location=":memory:",
+        ollama_embedding_model="nomic-embed-text",
+        vector_sync_enabled=False,  # Disable background sync for test
+    )
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.vector.qdrant_client.get_settings", lambda: mock_settings
+    )
+
+    # Mock embedding service - must have .provider attribute
+    from nextcloud_mcp_server.embedding import SimpleEmbeddingProvider
+
+    mock_provider = SimpleEmbeddingProvider(dimension=384)
+    mock_embedding_service = Mock()
+    mock_embedding_service.provider = mock_provider
+    mock_embedding_service.get_dimension = lambda: mock_provider.get_dimension()
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.embedding.get_embedding_service",
+        lambda: mock_embedding_service,
+    )
+
+    # Get client (should trigger collection creation)
+    client = await get_qdrant_client()
+
+    # Verify client is initialized
+    assert client is not None
+
+    # Verify collection was created
+    collection_name = mock_settings.get_collection_name()
+    collections = await client.get_collections()
+    collection_names = [c.name for c in collections.collections]
+    assert collection_name in collection_names
+
+    # Verify collection has correct dimensions
+    collection_info = await client.get_collection(collection_name)
+    assert collection_info.config.params.vectors.size == 384
+
+
+@pytest.mark.integration
+async def test_existing_collection_reused(monkeypatch):
+    """Test that existing collection is reused without error."""
+    # Mock settings
+    from nextcloud_mcp_server.config import Settings
+
+    mock_settings = Settings(
+        qdrant_location=":memory:",
+        ollama_embedding_model="nomic-embed-text",
+        vector_sync_enabled=False,
+    )
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.vector.qdrant_client.get_settings", lambda: mock_settings
+    )
+
+    # Mock embedding service - must have .provider attribute
+    from nextcloud_mcp_server.embedding import SimpleEmbeddingProvider
+
+    mock_provider = SimpleEmbeddingProvider(dimension=384)
+    mock_embedding_service = Mock()
+    mock_embedding_service.provider = mock_provider
+    mock_embedding_service.get_dimension = lambda: mock_provider.get_dimension()
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.embedding.get_embedding_service",
+        lambda: mock_embedding_service,
+    )
+
+    # First call - creates collection
+    _ = await get_qdrant_client()
+    collection_name = mock_settings.get_collection_name()
+
+    # Reset singleton to simulate second initialization
+    import nextcloud_mcp_server.vector.qdrant_client as qdrant_module
+
+    qdrant_module._qdrant_client = None
+
+    # Second call - should reuse existing collection
+    client2 = await get_qdrant_client()
+
+    # Verify both clients work
+    assert client2 is not None
+
+    # Verify collection still exists and wasn't recreated
+    collections = await client2.get_collections()
+    collection_names = [c.name for c in collections.collections]
+    assert collection_name in collection_names
+
+    # Verify dimensions unchanged
+    collection_info = await client2.get_collection(collection_name)
+    assert collection_info.config.params.vectors.size == 384
+
+
+@pytest.mark.integration
+async def test_dimension_mismatch_detected(monkeypatch, tmp_path):
+    """Test that dimension mismatch raises clear error."""
+    # Use persistent temp directory so collection survives client reset
+    from nextcloud_mcp_server.config import Settings
+
+    qdrant_path = str(tmp_path / "qdrant_data")
+    mock_settings = Settings(
+        qdrant_location=qdrant_path,
+        ollama_embedding_model="nomic-embed-text",
+        vector_sync_enabled=False,
+    )
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.vector.qdrant_client.get_settings", lambda: mock_settings
+    )
+
+    # First embedding service: 384 dimensions
+    from nextcloud_mcp_server.embedding import SimpleEmbeddingProvider
+
+    mock_provider_1 = SimpleEmbeddingProvider(dimension=384)
+    mock_embedding_service_1 = Mock()
+    mock_embedding_service_1.provider = mock_provider_1
+    mock_embedding_service_1.get_dimension = lambda: mock_provider_1.get_dimension()
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.embedding.get_embedding_service",
+        lambda: mock_embedding_service_1,
+    )
+
+    # First call - creates collection with 384 dimensions
+    client1 = await get_qdrant_client()
+    collection_name = mock_settings.get_collection_name()
+
+    # Verify collection created
+    collection_info = await client1.get_collection(collection_name)
+    assert collection_info.config.params.vectors.size == 384
+
+    # Close client1 to release file lock
+    await client1.close()
+
+    # Reset singleton (but collection persists in temp directory)
+    import nextcloud_mcp_server.vector.qdrant_client as qdrant_module
+
+    qdrant_module._qdrant_client = None
+
+    # Change embedding service to different dimension (768)
+    mock_provider_2 = SimpleEmbeddingProvider(dimension=768)
+    mock_embedding_service_2 = Mock()
+    mock_embedding_service_2.provider = mock_provider_2
+    mock_embedding_service_2.get_dimension = lambda: mock_provider_2.get_dimension()
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.embedding.get_embedding_service",
+        lambda: mock_embedding_service_2,
+    )
+
+    # Second call - should detect dimension mismatch and raise error
+    with pytest.raises(ValueError) as exc_info:
+        await get_qdrant_client()
+
+    # Verify error message is helpful
+    error_msg = str(exc_info.value)
+    assert "Dimension mismatch" in error_msg
+    assert "384" in error_msg  # Old dimension
+    assert "768" in error_msg  # New dimension
+    assert "Solutions:" in error_msg  # Includes helpful solutions
+
+
+@pytest.mark.integration
+async def test_idempotent_initialization(monkeypatch):
+    """Test that multiple calls to get_qdrant_client() are idempotent."""
+    # Mock settings
+    from nextcloud_mcp_server.config import Settings
+
+    mock_settings = Settings(
+        qdrant_location=":memory:",
+        ollama_embedding_model="nomic-embed-text",
+        vector_sync_enabled=False,
+    )
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.vector.qdrant_client.get_settings", lambda: mock_settings
+    )
+
+    # Mock embedding service - must have .provider attribute
+    from nextcloud_mcp_server.embedding import SimpleEmbeddingProvider
+
+    mock_provider = SimpleEmbeddingProvider(dimension=384)
+    mock_embedding_service = Mock()
+    mock_embedding_service.provider = mock_provider
+    mock_embedding_service.get_dimension = lambda: mock_provider.get_dimension()
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.embedding.get_embedding_service",
+        lambda: mock_embedding_service,
+    )
+
+    # Call multiple times
+    client1 = await get_qdrant_client()
+    client2 = await get_qdrant_client()
+    client3 = await get_qdrant_client()
+
+    # All should return same singleton instance
+    assert client1 is client2
+    assert client2 is client3
+
+    # Collection should exist
+    collection_name = mock_settings.get_collection_name()
+    collections = await client1.get_collections()
+    collection_names = [c.name for c in collections.collections]
+    assert collection_name in collection_names
+
+
+@pytest.mark.integration
+async def test_collection_name_generation(monkeypatch):
+    """Test that collection name is correctly generated from deployment ID and model."""
+    # Mock settings with custom deployment ID
+    from nextcloud_mcp_server.config import Settings
+
+    mock_settings = Settings(
+        qdrant_location=":memory:",
+        ollama_embedding_model="test-model",
+        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
+    )
+
+    # Mock embedding service - must have .provider attribute
+    from nextcloud_mcp_server.embedding import SimpleEmbeddingProvider
+
+    mock_provider = SimpleEmbeddingProvider(dimension=384)
+    mock_embedding_service = Mock()
+    mock_embedding_service.provider = mock_provider
+    mock_embedding_service.get_dimension = lambda: mock_provider.get_dimension()
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.embedding.get_embedding_service",
+        lambda: mock_embedding_service,
+    )
+
+    # Get client
+    client = await get_qdrant_client()
+
+    # Verify collection name includes deployment ID and model
+    collection_name = mock_settings.get_collection_name()
+    assert "test-deployment" in collection_name or "test-model" in collection_name
+
+    # Verify collection was created with that name
+    collections = await client.get_collections()
+    collection_names = [c.name for c in collections.collections]
+    assert collection_name in collection_names
+
+
+@pytest.mark.integration
+async def test_collection_uses_cosine_distance(monkeypatch):
+    """Test that created collection uses COSINE distance metric."""
+    # Mock settings
+    from nextcloud_mcp_server.config import Settings
+
+    mock_settings = Settings(
+        qdrant_location=":memory:",
+        ollama_embedding_model="nomic-embed-text",
+        vector_sync_enabled=False,
+    )
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.vector.qdrant_client.get_settings", lambda: mock_settings
+    )
+
+    # Mock embedding service - must have .provider attribute
+    from nextcloud_mcp_server.embedding import SimpleEmbeddingProvider
+
+    mock_provider = SimpleEmbeddingProvider(dimension=384)
+    mock_embedding_service = Mock()
+    mock_embedding_service.provider = mock_provider
+    mock_embedding_service.get_dimension = lambda: mock_provider.get_dimension()
+    monkeypatch.setattr(
+        "nextcloud_mcp_server.embedding.get_embedding_service",
+        lambda: mock_embedding_service,
+    )
+
+    # Get client (creates collection)
+    client = await get_qdrant_client()
+
+    # Verify collection uses COSINE distance
+    collection_name = mock_settings.get_collection_name()
+    collection_info = await client.get_collection(collection_name)
+
+    from qdrant_client.models import Distance
+
+    assert collection_info.config.params.vectors.distance == Distance.COSINE
@@ -28,7 +28,7 @@ import httpx
 from playwright.async_api import async_playwright

 from nextcloud_mcp_server.auth.client_registration import ensure_oauth_client
-from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.client import NextcloudClient
 from tests.load.oauth_metrics import OAuthBenchmarkMetrics
 from tests.load.oauth_pool import (
@@ -11,7 +11,7 @@ from unittest.mock import AsyncMock, MagicMock, patch
 import jwt
 import pytest

-from nextcloud_mcp_server.auth.refresh_token_storage import RefreshTokenStorage
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
 from nextcloud_mcp_server.auth.token_broker import TokenBrokerService
 from nextcloud_mcp_server.auth.token_exchange import TokenExchangeService

@@ -5,7 +5,7 @@ import os
 import pytest
 from click.testing import CliRunner

-from nextcloud_mcp_server.app import run
+from nextcloud_mcp_server.cli import run


@pytest.fixture
@@ -103,7 +103,7 @@ def test_cli_options_set_environment_variables(runner, clean_env, monkeypatch):
        raise SystemExit(0)

    # Patch get_app to capture env vars
-    monkeypatch.setattr("nextcloud_mcp_server.app.get_app", mock_get_app)
+    monkeypatch.setattr("nextcloud_mcp_server.cli.get_app", mock_get_app)

    _ = runner.invoke(
        run,
@@ -158,7 +158,7 @@ def test_cli_options_override_environment_variables(runner, monkeypatch):
        )
        raise SystemExit(0)

-    monkeypatch.setattr("nextcloud_mcp_server.app.get_app", mock_get_app)
+    monkeypatch.setattr("nextcloud_mcp_server.cli.get_app", mock_get_app)

    # Provide CLI options that should override env vars
    _ = runner.invoke(
@@ -211,7 +211,7 @@ def test_environment_variables_used_when_cli_not_provided(runner, monkeypatch):
        )
        raise SystemExit(0)

-    monkeypatch.setattr("nextcloud_mcp_server.app.get_app", mock_get_app)
+    monkeypatch.setattr("nextcloud_mcp_server.cli.get_app", mock_get_app)

    # Don't provide any CLI options - should use env vars
    _ = runner.invoke(run, [])
@@ -243,7 +243,7 @@ def test_default_values(runner, clean_env, monkeypatch):
        )
        raise SystemExit(0)

-    monkeypatch.setattr("nextcloud_mcp_server.app.get_app", mock_get_app)
+    monkeypatch.setattr("nextcloud_mcp_server.cli.get_app", mock_get_app)

    # Don't provide CLI options or env vars - should use defaults
    _ = runner.invoke(run, [])
@@ -275,7 +275,7 @@ def test_oauth_token_type_case_normalization(runner, clean_env, monkeypatch):
        )
        raise SystemExit(0)

-    monkeypatch.setattr("nextcloud_mcp_server.app.get_app", mock_get_app)
+    monkeypatch.setattr("nextcloud_mcp_server.cli.get_app", mock_get_app)

    # Test uppercase JWT
    runner.invoke(run, ["--oauth-token-type", "JWT"])
@@ -0,0 +1,112 @@
+"""Unit tests for webhook preset filtering."""
+
+import pytest
+
+from nextcloud_mcp_server.server.webhook_presets import (
+    filter_presets_by_installed_apps,
+    get_preset,
+    list_presets,
+)
+
+
+@pytest.mark.unit
+def test_list_all_presets():
+    """Test listing all presets returns 5 presets."""
+    presets = list_presets()
+    assert len(presets) == 5
+    preset_ids = [preset_id for preset_id, _ in presets]
+    assert "notes_sync" in preset_ids
+    assert "calendar_sync" in preset_ids
+    assert "tables_sync" in preset_ids
+    assert "forms_sync" in preset_ids
+    assert "files_sync" in preset_ids
+
+
+@pytest.mark.unit
+def test_get_preset_existing():
+    """Test getting an existing preset."""
+    preset = get_preset("notes_sync")
+    assert preset is not None
+    assert preset["name"] == "Notes Sync"
+    assert preset["app"] == "notes"
+    assert len(preset["events"]) == 3
+
+
+@pytest.mark.unit
+def test_get_preset_nonexistent():
+    """Test getting a nonexistent preset returns None."""
+    preset = get_preset("nonexistent_sync")
+    assert preset is None
+
+
+@pytest.mark.unit
+def test_filter_presets_all_apps_installed():
+    """Test filtering when all apps are installed."""
+    installed_apps = ["notes", "calendar", "tables", "forms"]
+    filtered = filter_presets_by_installed_apps(installed_apps)
+    assert len(filtered) == 5  # All 5 presets (files is always included)
+    preset_ids = [preset_id for preset_id, _ in filtered]
+    assert "notes_sync" in preset_ids
+    assert "calendar_sync" in preset_ids
+    assert "tables_sync" in preset_ids
+    assert "forms_sync" in preset_ids
+    assert "files_sync" in preset_ids
+
+
+@pytest.mark.unit
+def test_filter_presets_subset_installed():
+    """Test filtering when only some apps are installed."""
+    installed_apps = ["notes", "calendar"]
+    filtered = filter_presets_by_installed_apps(installed_apps)
+    assert len(filtered) == 3  # notes, calendar, files
+    preset_ids = [preset_id for preset_id, _ in filtered]
+    assert "notes_sync" in preset_ids
+    assert "calendar_sync" in preset_ids
+    assert "files_sync" in preset_ids
+    assert "tables_sync" not in preset_ids
+    assert "forms_sync" not in preset_ids
+
+
+@pytest.mark.unit
+def test_filter_presets_no_apps_installed():
+    """Test filtering when no optional apps are installed."""
+    installed_apps = []
+    filtered = filter_presets_by_installed_apps(installed_apps)
+    assert len(filtered) == 1  # Only files
+    preset_ids = [preset_id for preset_id, _ in filtered]
+    assert "files_sync" in preset_ids
+    assert "notes_sync" not in preset_ids
+    assert "calendar_sync" not in preset_ids
+
+
+@pytest.mark.unit
+def test_filter_presets_files_always_included():
+    """Test that files preset is always included regardless of installed apps."""
+    # Empty list
+    filtered = filter_presets_by_installed_apps([])
+    preset_ids = [preset_id for preset_id, _ in filtered]
+    assert "files_sync" in preset_ids
+
+    # List with other apps but not explicitly "files"
+    filtered = filter_presets_by_installed_apps(["notes", "calendar"])
+    preset_ids = [preset_id for preset_id, _ in filtered]
+    assert "files_sync" in preset_ids
+
+
+@pytest.mark.unit
+def test_filter_presets_forms_included_when_installed():
+    """Test that forms preset is included when Forms app is installed."""
+    installed_apps = ["forms"]
+    filtered = filter_presets_by_installed_apps(installed_apps)
+    preset_ids = [preset_id for preset_id, _ in filtered]
+    assert "forms_sync" in preset_ids
+    assert len(filtered) == 2  # forms + files
+
+
+@pytest.mark.unit
+def test_filter_presets_forms_excluded_when_not_installed():
+    """Test that forms preset is excluded when Forms app is not installed."""
+    installed_apps = ["notes", "calendar", "tables"]
+    filtered = filter_presets_by_installed_apps(installed_apps)
+    preset_ids = [preset_id for preset_id, _ in filtered]
+    assert "forms_sync" not in preset_ids
@@ -0,0 +1,195 @@
+"""
+Unit tests for Webhook Storage functionality.
+
+Tests the webhook tracking methods in RefreshTokenStorage without
+requiring real database connections or network calls.
+"""
+
+import tempfile
+import time
+from pathlib import Path
+
+import pytest
+
+from nextcloud_mcp_server.auth.storage import RefreshTokenStorage
+
+pytestmark = pytest.mark.unit
+
+
+@pytest.fixture
+async def temp_storage():
+    """Create temporary storage instance for testing."""
+    with tempfile.TemporaryDirectory() as tmpdir:
+        db_path = Path(tmpdir) / "test_webhooks.db"
+        # No encryption key needed for webhook tracking
+        storage = RefreshTokenStorage(db_path=str(db_path), encryption_key=None)
+        await storage.initialize()
+        yield storage
+
+
+async def test_store_webhook(temp_storage):
+    """Test storing a webhook."""
+    await temp_storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+
+    webhooks = await temp_storage.list_all_webhooks()
+    assert len(webhooks) == 1
+    assert webhooks[0]["webhook_id"] == 123
+    assert webhooks[0]["preset_id"] == "notes_sync"
+    assert "created_at" in webhooks[0]
+
+
+async def test_store_webhook_duplicate(temp_storage):
+    """Test storing duplicate webhook replaces existing."""
+    await temp_storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+    await temp_storage.store_webhook(webhook_id=123, preset_id="calendar_sync")
+
+    webhooks = await temp_storage.list_all_webhooks()
+    # Should only have one entry due to UNIQUE constraint
+    assert len(webhooks) == 1
+    assert webhooks[0]["preset_id"] == "calendar_sync"
+
+
+async def test_get_webhooks_by_preset(temp_storage):
+    """Test retrieving webhooks by preset."""
+    await temp_storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+    await temp_storage.store_webhook(webhook_id=456, preset_id="notes_sync")
+    await temp_storage.store_webhook(webhook_id=789, preset_id="calendar_sync")
+
+    notes_webhooks = await temp_storage.get_webhooks_by_preset("notes_sync")
+    assert len(notes_webhooks) == 2
+    assert 123 in notes_webhooks
+    assert 456 in notes_webhooks
+
+    calendar_webhooks = await temp_storage.get_webhooks_by_preset("calendar_sync")
+    assert len(calendar_webhooks) == 1
+    assert 789 in calendar_webhooks
+
+
+async def test_get_webhooks_by_preset_empty(temp_storage):
+    """Test retrieving webhooks for non-existent preset."""
+    webhooks = await temp_storage.get_webhooks_by_preset("nonexistent")
+    assert len(webhooks) == 0
+
+
+async def test_delete_webhook(temp_storage):
+    """Test deleting a webhook."""
+    await temp_storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+    await temp_storage.store_webhook(webhook_id=456, preset_id="notes_sync")
+
+    deleted = await temp_storage.delete_webhook(webhook_id=123)
+    assert deleted is True
+
+    webhooks = await temp_storage.get_webhooks_by_preset("notes_sync")
+    assert len(webhooks) == 1
+    assert 456 in webhooks
+
+
+async def test_delete_webhook_nonexistent(temp_storage):
+    """Test deleting non-existent webhook."""
+    deleted = await temp_storage.delete_webhook(webhook_id=999)
+    assert deleted is False
+
+
+async def test_list_all_webhooks(temp_storage):
+    """Test listing all webhooks."""
+    await temp_storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+    await temp_storage.store_webhook(webhook_id=456, preset_id="calendar_sync")
+    await temp_storage.store_webhook(webhook_id=789, preset_id="notes_sync")
+
+    webhooks = await temp_storage.list_all_webhooks()
+    assert len(webhooks) == 3
+
+    # Verify all expected fields present
+    for webhook in webhooks:
+        assert "webhook_id" in webhook
+        assert "preset_id" in webhook
+        assert "created_at" in webhook
+
+    # Verify webhook IDs
+    webhook_ids = [w["webhook_id"] for w in webhooks]
+    assert 123 in webhook_ids
+    assert 456 in webhook_ids
+    assert 789 in webhook_ids
+
+
+async def test_list_all_webhooks_empty(temp_storage):
+    """Test listing webhooks when none exist."""
+    webhooks = await temp_storage.list_all_webhooks()
+    assert len(webhooks) == 0
+
+
+async def test_clear_preset_webhooks(temp_storage):
+    """Test clearing all webhooks for a preset."""
+    await temp_storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+    await temp_storage.store_webhook(webhook_id=456, preset_id="notes_sync")
+    await temp_storage.store_webhook(webhook_id=789, preset_id="calendar_sync")
+
+    deleted_count = await temp_storage.clear_preset_webhooks("notes_sync")
+    assert deleted_count == 2
+
+    # Verify notes_sync webhooks are gone
+    notes_webhooks = await temp_storage.get_webhooks_by_preset("notes_sync")
+    assert len(notes_webhooks) == 0
+
+    # Verify calendar_sync webhook still exists
+    calendar_webhooks = await temp_storage.get_webhooks_by_preset("calendar_sync")
+    assert len(calendar_webhooks) == 1
+    assert 789 in calendar_webhooks
+
+
+async def test_clear_preset_webhooks_nonexistent(temp_storage):
+    """Test clearing webhooks for non-existent preset."""
+    deleted_count = await temp_storage.clear_preset_webhooks("nonexistent")
+    assert deleted_count == 0
+
+
+async def test_webhook_timestamps(temp_storage):
+    """Test that webhook timestamps are properly stored."""
+    start_time = time.time()
+    await temp_storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+    end_time = time.time()
+
+    webhooks = await temp_storage.list_all_webhooks()
+    assert len(webhooks) == 1
+
+    created_at = webhooks[0]["created_at"]
+    assert start_time <= created_at <= end_time
+
+
+async def test_storage_without_encryption_key():
+    """Test that storage can be initialized without encryption key."""
+    with tempfile.TemporaryDirectory() as tmpdir:
+        db_path = Path(tmpdir) / "test_no_encryption.db"
+        storage = RefreshTokenStorage(db_path=str(db_path), encryption_key=None)
+        await storage.initialize()
+
+        # Webhook operations should work without encryption key
+        await storage.store_webhook(webhook_id=123, preset_id="notes_sync")
+        webhooks = await storage.get_webhooks_by_preset("notes_sync")
+        assert len(webhooks) == 1
+        assert 123 in webhooks
+
+
+async def test_multiple_presets_independence(temp_storage):
+    """Test that different presets maintain independent webhook lists."""
+    presets = ["notes_sync", "calendar_sync", "deck_sync", "files_sync"]
+
+    # Store webhooks for each preset
+    for i, preset in enumerate(presets):
+        webhook_id = 100 + i
+        await temp_storage.store_webhook(webhook_id=webhook_id, preset_id=preset)
+
+    # Verify each preset has exactly one webhook
+    for i, preset in enumerate(presets):
+        webhooks = await temp_storage.get_webhooks_by_preset(preset)
+        assert len(webhooks) == 1
+        assert (100 + i) in webhooks
+
+    # Clear one preset
+    deleted = await temp_storage.clear_preset_webhooks("notes_sync")
+    assert deleted == 1
+
+    # Verify other presets unchanged
+    for preset in ["calendar_sync", "deck_sync", "files_sync"]:
+        webhooks = await temp_storage.get_webhooks_by_preset(preset)
+        assert len(webhooks) == 1
@@ -2,15 +2,9 @@ version = 1
 revision = 3
 requires-python = ">=3.11"
 resolution-markers = [
-    "python_full_version < '3.12' and sys_platform == 'darwin'",
-    "python_full_version < '3.12' and platform_machine == 'aarch64' and sys_platform == 'linux'",
-    "(python_full_version < '3.12' and platform_machine != 'aarch64' and sys_platform == 'linux') or (python_full_version < '3.12' and sys_platform != 'darwin' and sys_platform != 'linux')",
-    "python_full_version == '3.12.*' and sys_platform == 'darwin'",
-    "python_full_version == '3.12.*' and platform_machine == 'aarch64' and sys_platform == 'linux'",
-    "(python_full_version == '3.12.*' and platform_machine != 'aarch64' and sys_platform == 'linux') or (python_full_version == '3.12.*' and sys_platform != 'darwin' and sys_platform != 'linux')",
-    "python_full_version >= '3.13' and sys_platform == 'darwin'",
-    "python_full_version >= '3.13' and platform_machine == 'aarch64' and sys_platform == 'linux'",
-    "(python_full_version >= '3.13' and platform_machine != 'aarch64' and sys_platform == 'linux') or (python_full_version >= '3.13' and sys_platform != 'darwin' and sys_platform != 'linux')",
+    "python_full_version >= '3.13'",
+    "python_full_version == '3.12.*'",
+    "python_full_version < '3.12'",
 ]

 [[package]]
@@ -50,11 +44,11 @@ wheels = [

 [[package]]
 name = "argcomplete"
-version = "3.6.2"
+version = "3.6.3"
 source = { registry = "https://pypi.org/simple" }
-sdist = { url = "https://files.pythonhosted.org/packages/16/0f/861e168fc813c56a78b35f3c30d91c6757d1fd185af1110f1aec784b35d0/argcomplete-3.6.2.tar.gz", hash = "sha256:d0519b1bc867f5f4f4713c41ad0aba73a4a5f007449716b16f385f2166dc6adf", size = 73403, upload-time = "2025-04-03T04:57:03.52Z" }
+sdist = { url = "https://files.pythonhosted.org/packages/38/61/0b9ae6399dd4a58d8c1b1dc5a27d6f2808023d0b5dd3104bb99f45a33ff6/argcomplete-3.6.3.tar.gz", hash = "sha256:62e8ed4fd6a45864acc8235409461b72c9a28ee785a2011cc5eb78318786c89c", size = 73754, upload-time = "2025-10-20T03:33:34.741Z" }
 wheels = [
-    { url = "https://files.pythonhosted.org/packages/31/da/e42d7a9d8dd33fa775f467e4028a47936da2f01e4b0e561f9ba0d74cb0ca/argcomplete-3.6.2-py3-none-any.whl", hash = "sha256:65b3133a29ad53fb42c48cf5114752c7ab66c1c38544fdf6460f450c09b42591", size = 43708, upload-time = "2025-04-03T04:57:01.591Z" },
+    { url = "https://files.pythonhosted.org/packages/74/f5/9373290775639cb67a2fce7f629a1c240dce9f12fe927bc32b2736e16dfc/argcomplete-3.6.3-py3-none-any.whl", hash = "sha256:f5007b3a600ccac5d25bbce33089211dfd49eab4a7718da3f10e3082525a92ce", size = 43846, upload-time = "2025-10-20T03:33:33.021Z" },
 ]

 [[package]]
@@ -98,8 +92,8 @@ wheels = [

 [[package]]
 name = "caldav"
-version = "2.0.2.dev38+g1aa2be35e"
-source = { git = "https://github.com/cbcoutinho/caldav?branch=feature%2Fhttpx#1aa2be35e94883b44efd42f1cd82d281f8f58e60" }
+version = "2.0.2.dev47+g3e44cf827"
+source = { git = "https://github.com/cbcoutinho/caldav?branch=feature%2Fhttpx#3e44cf827e392a0073a16a6b01e299ecef02404b" }
 dependencies = [
    { name = "httpx", extra = ["http2"] },
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 [[package]]
@@ -0,0 +1,532 @@
+# Nextcloud Webhook Testing Findings
+
+**Date:** 2025-11-11
+**Purpose:** Manual validation of Nextcloud webhook schemas and behavior for vector sync integration (ADR-010)
+
+## Executive Summary
+
+Successfully tested and validated Nextcloud webhook payloads for file/note events and calendar events. **5 out of 6** webhook types were captured and validated against expected schemas from ADR-010 and Nextcloud documentation. One calendar deletion webhook did not fire during testing (potential Nextcloud issue or configuration).
+
+## Test Environment
+
+- **Nextcloud Version:** 30+ (Docker compose setup)
+- **Webhook App:** `webhook_listeners` (bundled, enabled)
+- **MCP Server:** Test endpoint at `http://mcp:8000/webhooks/nextcloud`
+- **Background Worker:** Running with 60s timeout
+- **Authentication:** None (test environment)
+
+## Webhooks Registered
+
+| ID | Event Class | Status |
+|----|------------|--------|
+| 1 | `OCP\Files\Events\Node\NodeCreatedEvent` | ✓ Tested |
+| 2 | `OCP\Files\Events\Node\NodeWrittenEvent` | ✓ Tested |
+| 3 | `OCP\Files\Events\Node\NodeDeletedEvent` | ✓ Tested |
+| 4 | `OCP\Calendar\Events\CalendarObjectCreatedEvent` | ✓ Tested |
+| 5 | `OCP\Calendar\Events\CalendarObjectUpdatedEvent` | ✓ Tested |
+| 6 | `OCP\Calendar\Events\CalendarObjectDeletedEvent` | ✗ Not received |
+
+## Captured Webhook Payloads
+
+### 1. NodeCreatedEvent (File/Note Creation)
+
+**Test Action:** Created note via Notes API
+**Trigger Time:** 2025-11-11 08:37:25
+**Webhooks Fired:** 3 events (folder creation + file creation + file written)
+
+**Payload:**
+```json
+{
+  "user": {
+    "uid": "admin",
+    "displayName": "admin"
+  },
+  "time": 1762850245,
+  "event": {
+    "class": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+    "node": {
+      "id": 437,
+      "path": "/admin/files/Notes/Webhooks/Webhook Test Note.md"
+    }
+  }
+}
+```
+
+**Validation:**
+- ✅ Schema matches ADR-010 specification
+- ✅ Contains `user` object with `uid` and `displayName`
+- ✅ Contains `time` (Unix timestamp)
+- ✅ Contains `event.class` (fully qualified event name)
+- ✅ Contains `event.node.id` (file ID)
+- ✅ Contains `event.node.path` (absolute path)
+
+**Observations:**
+- Creating a note via Notes API triggers 3 webhook events:
+  1. `NodeCreatedEvent` for the parent folder (if new)
+  2. `NodeWrittenEvent` for the parent folder
+  3. `NodeCreatedEvent` for the actual file
+  4. `NodeWrittenEvent` for the file (sometimes fired 2x)
+
+### 2. NodeWrittenEvent (File/Note Update)
+
+**Test Action:** Updated note content via Notes API
+**Trigger Time:** 2025-11-11 08:49:20
+
+**Payload:**
+```json
+{
+  "user": {
+    "uid": "admin",
+    "displayName": "admin"
+  },
+  "time": 1762850960,
+  "event": {
+    "class": "OCP\\Files\\Events\\Node\\NodeWrittenEvent",
+    "node": {
+      "id": 437,
+      "path": "/admin/files/Notes/Webhooks/Webhook Test Note.md"
+    }
+  }
+}
+```
+
+**Validation:**
+- ✅ Schema identical to `NodeCreatedEvent` except for `event.class`
+- ✅ Same file ID (437) as creation event
+- ✅ Updated timestamp reflects actual modification time
+
+**Observations:**
+- File updates trigger a single `NodeWrittenEvent`
+- No duplicate events fired for update operations
+
+### 3. NodeDeletedEvent (File/Note Deletion)
+
+**Test Action:** Deleted note via Notes API
+**Trigger Time:** 2025-11-11 08:51:34
+**Webhooks Fired:** 2 events (file + folder deletion)
+
+**Payload:**
+```json
+{
+  "user": {
+    "uid": "admin",
+    "displayName": "admin"
+  },
+  "time": 1762851093,
+  "event": {
+    "class": "OCP\\Files\\Events\\Node\\NodeDeletedEvent",
+    "node": {
+      "path": "/admin/files/Notes/Webhooks/Webhook Test Note.md"
+    }
+  }
+}
+```
+
+**Validation:**
+- ✅ Schema matches ADR-010 specification
+- ⚠️  **IMPORTANT:** No `node.id` field in deletion events (only `path`)
+- ✅ Folder deletion triggered after file deletion (empty folder cleanup)
+
+**Observations:**
+- **Critical Difference:** Deletion events do NOT include `node.id`, only `node.path`
+- This differs from Create/Write events which include both `id` and `path`
+- ADR-010 implementation must handle missing `id` field for deletions
+- Deleting a file also triggers deletion of empty parent folders
+
+### 4. CalendarObjectCreatedEvent (Calendar Event Creation)
+
+**Test Action:** Created calendar event via CalDAV PUT
+**Trigger Time:** 2025-11-11 08:52:50
+
+**Payload (partial - calendarData omitted for brevity):**
+```json
+{
+  "user": {
+    "uid": "admin",
+    "displayName": "admin"
+  },
+  "time": 1762851169,
+  "event": {
+    "calendarId": 1,
+    "class": "OCP\\Calendar\\Events\\CalendarObjectCreatedEvent",
+    "calendarData": {
+      "id": 1,
+      "uri": "personal",
+      "{http://calendarserver.org/ns/}getctag": "...",
+      "{http://sabredav.org/ns}sync-token": 21,
+      "{urn:ietf:params:xml:ns:caldav}supported-calendar-component-set": [],
+      "{urn:ietf:params:xml:ns:caldav}schedule-calendar-transp": [],
+      "{urn:ietf:params:xml:ns:caldav}calendar-timezone": null
+    },
+    "objectData": {
+      "id": 3,
+      "uri": "webhook-test-event-001.ics",
+      "lastmodified": 1762851169,
+      "etag": "\"2b937b7d77dc83c77329dfdb210ba9d0\"",
+      "calendarid": 1,
+      "size": 297,
+      "component": "vevent",
+      "classification": 0,
+      "uid": "webhook-test-event-001@nextcloud",
+      "calendardata": "BEGIN:VCALENDAR\r\nVERSION:2.0\r\n...",
+      "{http://nextcloud.com/ns}deleted-at": null
+    },
+    "shares": []
+  }
+}
+```
+
+**Validation:**
+- ✅ Schema matches Nextcloud documentation
+- ✅ Contains complete calendar metadata (`calendarData`)
+- ✅ Contains complete event data (`objectData`)
+- ✅ Includes full iCal data in `objectData.calendardata`
+- ✅ Includes `objectData.id` for database lookups
+- ⚠️  **Complex:** Much more metadata than file events
+
+**Observations:**
+- Calendar webhooks include significantly more data than file webhooks
+- Full iCal content is embedded in `objectData.calendardata`
+- Event ID is in `objectData.id` (NOT `event.id`)
+- `calendarData` contains calendar-level metadata
+- `shares` array contains sharing information (empty in this test)
+
+### 5. CalendarObjectUpdatedEvent (Calendar Event Update)
+
+**Test Action:** Updated calendar event via CalDAV PUT
+**Trigger Time:** 2025-11-11 08:53:28
+
+**Payload (partial):**
+```json
+{
+  "user": {
+    "uid": "admin",
+    "displayName": "admin"
+  },
+  "time": 1762851207,
+  "event": {
+    "calendarId": 1,
+    "class": "OCP\\Calendar\\Events\\CalendarObjectUpdatedEvent",
+    "calendarData": { /* same structure as creation */ },
+    "objectData": {
+      "id": 3,
+      "uri": "webhook-test-event-001.ics",
+      "lastmodified": 1762851207,
+      "etag": "\"2695a18013e0991e4212b07b61d5e1e2\"",
+      "calendarid": 1,
+      "size": 315,
+      "component": "vevent",
+      "classification": 0,
+      "uid": "webhook-test-event-001@nextcloud",
+      "calendardata": "BEGIN:VCALENDAR\r\nVERSION:2.0\r\n...",
+      "{http://nextcloud.com/ns}deleted-at": null
+    },
+    "shares": []
+  }
+}
+```
+
+**Validation:**
+- ✅ Schema identical to `CalendarObjectCreatedEvent` except `event.class`
+- ✅ Same event ID (3) as creation
+- ✅ Updated `lastmodified` timestamp
+- ✅ Different `etag` (changed from creation)
+- ✅ Larger `size` (315 vs 297 bytes)
+
+**Observations:**
+- Update events contain full new state (not delta)
+- ETag changes on updates (useful for conflict detection)
+- Size field reflects actual iCal size
+
+### 6. CalendarObjectDeletedEvent (Calendar Event Deletion)
+
+**Test Action:** Deleted calendar event via CalDAV DELETE
+**Trigger Time:** 2025-11-11 08:54:47
+**Status:** ❌ **WEBHOOK DID NOT FIRE**
+
+**Expected Payload (from Nextcloud docs):**
+```json
+{
+  "user": {
+    "uid": "admin",
+    "displayName": "admin"
+  },
+  "time": <timestamp>,
+  "event": {
+    "calendarId": 1,
+    "class": "OCP\\Calendar\\Events\\CalendarObjectDeletedEvent",
+    "calendarData": { /* calendar metadata */ },
+    "objectData": {
+      "id": 3,
+      "uri": "webhook-test-event-001.ics",
+      /* ... other fields ... */
+    },
+    "shares": []
+  }
+}
+```
+
+**Issue:**
+- Calendar event was successfully deleted (verified via CalDAV PROPFIND)
+- Webhook registration confirmed (ID #6 in `webhook_listeners:list`)
+- Background worker running and processing other events
+- **No webhook notification received after 2+ minutes**
+
+**Possible Causes:**
+1. Known Nextcloud bug with calendar deletion webhooks
+2. CalDAV DELETE may not trigger event system properly
+3. Deletion event may require trash bin enabled
+4. Background job may have silently failed
+
+**Recommended Actions:**
+- File Nextcloud issue report
+- Test with trash bin enabled (`CalendarObjectMovedToTrashEvent`)
+- Check Nextcloud error logs for webhook failures
+- Verify with Nextcloud 31+ if issue persists
+
+## Schema Comparison: Expected vs Actual
+
+### File Events
+
+| Field | Expected (ADR-010) | Actual | Match |
+|-------|-------------------|--------|-------|
+| `user.uid` | string | string | ✅ |
+| `user.displayName` | string | string | ✅ |
+| `time` | int | int | ✅ |
+| `event.class` | string | string | ✅ |
+| `event.node.id` | string | int | ⚠️ Type mismatch |
+| `event.node.path` | string | string | ✅ |
+
+**Type Discrepancy:** `node.id` is documented as `string` but returns as `int` (437 instead of "437")
+
+### Calendar Events
+
+| Field | Expected (Nextcloud docs) | Actual | Match |
+|-------|-------------------------|--------|-------|
+| `user.uid` | string | string | ✅ |
+| `user.displayName` | string | string | ✅ |
+| `time` | int | int | ✅ |
+| `event.class` | string | string | ✅ |
+| `event.calendarId` | int | int | ✅ |
+| `event.calendarData.*` | object | object | ✅ |
+| `event.objectData.id` | int | int | ✅ |
+| `event.objectData.uri` | string | string | ✅ |
+| `event.objectData.calendardata` | string | string | ✅ |
+| `event.objectData.lastmodified` | int | int | ✅ |
+| `event.objectData.etag` | string | string | ✅ |
+| `event.objectData.component` | string\|null | string | ✅ |
+| `event.shares` | array | array | ✅ |
+
+All calendar event fields match expected schemas.
+
+## Key Findings for ADR-010 Implementation
+
+### 1. Deletion Events Have Different Schema
+- **File Deletions:** No `node.id` field, only `node.path`
+- **Calendar Deletions:** Not tested (webhook didn't fire)
+- **Impact:** Webhook handler must check for `node.id` existence before using it
+
+### 2. Multiple Webhooks Per Operation
+- Creating a note triggers 3-5 webhook events
+- Deleting a note triggers 2 events (file + folder)
+- **Impact:** Deduplication logic needed in webhook handler
+
+### 3. Event-Specific ID Fields
+- **File events:** `event.node.id`
+- **Calendar events:** `event.objectData.id`
+- **Impact:** Event parser must handle different ID field locations
+
+### 4. Full State vs Delta
+- All webhooks contain complete current state (not delta)
+- **Impact:** No need for "previous state" tracking in webhook handler
+
+### 5. Calendar Data Richness
+- Calendar webhooks include full iCal content
+- **Impact:** Can extract all event metadata without additional API calls
+
+## Recommendations for ADR-010 Implementation
+
+### 1. Webhook Event Parser (`webhook_parser.py`)
+
+```python
+def extract_document_task(event_class: str, payload: dict) -> DocumentTask | None:
+    """Extract DocumentTask from webhook event payload."""
+    user_id = payload["user"]["uid"]
+    event_data = payload["event"]
+
+    # File/Note events
+    if "NodeCreatedEvent" in event_class or "NodeWrittenEvent" in event_class:
+        path = event_data["node"]["path"]
+
+        # Only process markdown files for notes
+        if not path.endswith(".md"):
+            return None
+
+        # IMPORTANT: Check if 'id' exists (missing in deletion events)
+        doc_id = str(event_data["node"].get("id", ""))
+        if not doc_id:
+            # For missing ID, use path-based identifier
+            doc_id = f"path:{path}"
+
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=doc_id,
+            doc_type="note",
+            operation="index",
+            modified_at=payload["time"],
+        )
+
+    # File deletion events
+    elif "NodeDeletedEvent" in event_class:
+        path = event_data["node"]["path"]
+
+        if not path.endswith(".md"):
+            return None
+
+        # Deletion events DON'T have node.id - use path
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=f"path:{path}",  # Path-based since ID unavailable
+            doc_type="note",
+            operation="delete",
+            modified_at=payload["time"],
+        )
+
+    # Calendar creation/update events
+    elif "CalendarObjectCreatedEvent" in event_class or \
+         "CalendarObjectUpdatedEvent" in event_class:
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=str(event_data["objectData"]["id"]),
+            doc_type="calendar_event",
+            operation="index",
+            modified_at=event_data["objectData"]["lastmodified"],
+        )
+
+    # Calendar deletion events
+    elif "CalendarObjectDeletedEvent" in event_class:
+        return DocumentTask(
+            user_id=user_id,
+            doc_id=str(event_data["objectData"]["id"]),
+            doc_type="calendar_event",
+            operation="delete",
+            modified_at=payload["time"],
+        )
+
+    return None  # Unsupported event type
+```
+
+### 2. Deduplication Strategy
+
+**Problem:** Creating a note triggers 3-5 webhooks
+**Solution:** Idempotent processing + task deduplication
+
+```python
+# In webhook handler
+async def handle_nextcloud_webhook(request: Request) -> JSONResponse:
+    payload = await request.json()
+
+    task = extract_document_task(
+        payload["event"]["class"],
+        payload
+    )
+
+    if task:
+        # Idempotent: Queue will only process latest version
+        await document_queue.send(task)
+
+    return JSONResponse({"status": "received"}, status_code=200)
+```
+
+### 3. Path-Based Fallback for Deletions
+
+Since deletion events lack `node.id`, use path-based identification:
+
+```python
+# In Qdrant delete logic
+async def delete_document(user_id: str, doc_id: str, doc_type: str):
+    if doc_id.startswith("path:"):
+        # Path-based deletion
+        path = doc_id.removeprefix("path:")
+        # Search Qdrant for document with matching path in metadata
+        points = await qdrant.scroll(
+            collection_name=collection,
+            scroll_filter=Filter(must=[
+                FieldCondition(
+                    key="user_id",
+                    match=MatchValue(value=user_id),
+                ),
+                FieldCondition(
+                    key="metadata.path",
+                    match=MatchValue(value=path),
+                ),
+            ]),
+        )
+        # Delete found points
+    else:
+        # ID-based deletion (normal case)
+        ...
+```
+
+### 4. Webhook Registration Filters
+
+To reduce webhook volume, add filters:
+
+```json
+{
+  "httpMethod": "POST",
+  "uri": "http://mcp:8000/webhooks/nextcloud",
+  "event": "OCP\\Files\\Events\\Node\\NodeCreatedEvent",
+  "eventFilter": {
+    "event.node.path": "/^.*\\.md$/"
+  }
+}
+```
+
+This filters to only `.md` files at the webhook registration level (not handler level).
+
+### 5. Monitoring and Metrics
+
+Add webhook-specific metrics:
+
+```python
+webhook_notifications_received_total{event_type="note_created"} 42
+webhook_processing_duration_seconds{event_type="note_created"} 0.023
+webhook_errors_total{error_type="parse_error"} 2
+webhook_duplicates_filtered_total{doc_type="note"} 15
+```
+
+## Testing Checklist for Implementation
+
+- [x] File creation webhook triggers document indexing
+- [x] File update webhook triggers reindexing
+- [x] File deletion webhook triggers document removal
+- [ ] File deletion without ID successfully removes document (path-based)
+- [x] Calendar creation webhook triggers event indexing
+- [x] Calendar update webhook triggers event reindexing
+- [ ] Calendar deletion webhook triggers event removal (NOT TESTED - webhook didn't fire)
+- [ ] Duplicate webhooks are deduplicated
+- [ ] Non-markdown file webhooks are ignored
+- [ ] Malformed webhook payloads return 400 error
+- [ ] Webhook authentication validates shared secret
+- [ ] Webhook processing completes within 50ms
+
+## Appendix: Raw Webhook Logs
+
+Complete webhook logs with full payloads are available in MCP container logs:
+
+```bash
+docker compose logs mcp | grep -A 30 "🔔 Webhook received"
+```
+
+## Conclusion
+
+Nextcloud webhooks work as documented with minor exceptions:
+
+1. ✅ **File/Note Events:** Fully functional and match expected schemas
+2. ✅ **Calendar Creation/Update:** Fully functional with rich metadata
+3. ❌ **Calendar Deletion:** Webhook did not fire (requires investigation)
+4. ⚠️  **Schema Discrepancy:** `node.id` is integer (not string as documented)
+5. ⚠️  **Deletion Schema:** Missing `node.id` field (only `path` provided)
+
+**Overall Status:** Ready for ADR-010 implementation with noted caveats. Calendar deletion webhook issue should be reported to Nextcloud and may require alternative approach (polling or trash bin events).