diff --git a/.github/workflows/rag-evaluation.yml b/.github/workflows/rag-evaluation.yml
new file mode 100644
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+++ b/.github/workflows/rag-evaluation.yml
@@ -0,0 +1,271 @@
+name: RAG Evaluation
+
+on:
+  workflow_dispatch:
+    inputs:
+      embedding_model:
+        description: 'OpenAI embedding model'
+        required: false
+        default: 'openai/text-embedding-3-small'
+      generation_model:
+        description: 'OpenAI generation model'
+        required: false
+        default: 'openai/gpt-4o-mini'
+
+jobs:
+  rag-evaluation:
+    runs-on: ubuntu-latest
+    timeout-minutes: 45
+
+    steps:
+      - uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
+        with:
+          submodules: 'true'
+
+      - name: Clone Nextcloud documentation
+        uses: actions/checkout@1af3b93b6815bc44a9784bd300feb67ff0d1eeb3 # v6.0.0
+        with:
+          repository: 'nextcloud/documentation'
+          path: 'nextcloud-docs'
+
+      - name: Install Sphinx and LaTeX dependencies
+        run: |
+          sudo apt-get update
+          sudo apt-get install -y \
+            python3-sphinx \
+            python3-pip \
+            latexmk \
+            texlive-latex-recommended \
+            texlive-latex-extra \
+            texlive-fonts-recommended \
+            texlive-fonts-extra
+
+      - name: Build User Manual PDF
+        run: |
+          cd nextcloud-docs/user_manual
+          pip3 install -r ../requirements.txt
+          make latexpdf
+          ls -la _build/latex/
+          cp _build/latex/NextcloudUserManual.pdf ../../Nextcloud_User_Manual.pdf
+          echo "PDF built successfully"
+
+      ###### Required to build OIDC App ######
+      - name: Set up php 8.4
+        uses: shivammathur/setup-php@bf6b4fbd49ca58e4608c9c89fba0b8d90bd2a39f # v2
+        with:
+          php-version: 8.4
+          coverage: none
+
+      - name: Install OIDC app composer dependencies
+        run: |
+          cd third_party/oidc
+          composer install --no-dev
+      ###### Required to build OIDC App ######
+
+      - name: Run docker compose with vector sync
+        uses: hoverkraft-tech/compose-action@3846bcd61da338e9eaaf83e7ed0234a12b099b72 # v2.4.1
+        with:
+          compose-file: "./docker-compose.yml"
+          up-flags: "--build"
+        env:
+          # Override MCP container environment for OpenAI + vector sync
+          VECTOR_SYNC_ENABLED: "true"
+          VECTOR_SYNC_SCAN_INTERVAL: "30"
+          OPENAI_API_KEY: ${{ secrets.GITHUB_TOKEN }}
+          OPENAI_BASE_URL: "https://models.github.ai/inference"
+          OPENAI_EMBEDDING_MODEL: ${{ inputs.embedding_model }}
+          OPENAI_GENERATION_MODEL: ${{ inputs.generation_model }}
+
+      - name: Install the latest version of uv
+        uses: astral-sh/setup-uv@1e862dfacbd1d6d858c55d9b792c756523627244 # v7.1.4
+
+      - name: Wait for Nextcloud to be ready
+        run: |
+          echo "Waiting for Nextcloud..."
+          max_attempts=60
+          attempt=0
+          until curl -o /dev/null -s -w "%{http_code}\n" http://localhost:8080/ocs/v2.php/apps/serverinfo/api/v1/info | grep -q "401"; do
+            attempt=$((attempt + 1))
+            if [ $attempt -ge $max_attempts ]; then
+              echo "Service did not become ready in time."
+              exit 1
+            fi
+            echo "Attempt $attempt/$max_attempts: Service not ready, sleeping for 5 seconds..."
+            sleep 5
+          done
+          echo "Nextcloud is ready."
+
+      - name: Wait for MCP server to be ready
+        run: |
+          echo "Waiting for MCP server..."
+          max_attempts=30
+          attempt=0
+          until curl -o /dev/null -s -w "%{http_code}\n" http://localhost:8000/health | grep -q "200"; do
+            attempt=$((attempt + 1))
+            if [ $attempt -ge $max_attempts ]; then
+              echo "MCP server did not become ready in time."
+              exit 1
+            fi
+            echo "Attempt $attempt/$max_attempts: MCP not ready, sleeping for 2 seconds..."
+            sleep 2
+          done
+          echo "MCP server is ready."
+
+      - name: Upload User Manual PDF to Nextcloud
+        run: |
+          echo "Uploading Nextcloud_User_Manual.pdf to Nextcloud..."
+          HTTP_CODE=$(curl -s -o /dev/null -w "%{http_code}" -u admin:admin \
+            -X PUT \
+            -T Nextcloud_User_Manual.pdf \
+            "http://localhost:8080/remote.php/dav/files/admin/Nextcloud_User_Manual.pdf")
+
+          if [ "$HTTP_CODE" = "201" ] || [ "$HTTP_CODE" = "204" ]; then
+            echo "PDF uploaded successfully (HTTP $HTTP_CODE)"
+          else
+            echo "Failed to upload PDF (HTTP $HTTP_CODE)"
+            exit 1
+          fi
+
+      - name: Create vector-index tag
+        id: create_tag
+        run: |
+          # Create the tag using OCS API
+          echo "Creating vector-index tag..."
+          RESPONSE=$(curl -s -u admin:admin \
+            -X POST \
+            -H 'Content-Type: application/json' \
+            -H 'OCS-APIRequest: true' \
+            -d '{"name":"vector-index","userVisible":true,"userAssignable":true}' \
+            "http://localhost:8080/ocs/v2.php/apps/systemtags/api/v1/tags")
+
+          echo "Create tag response: $RESPONSE"
+
+          # Get tag ID from response or lookup
+          TAG_ID=$(echo "$RESPONSE" | grep -oP '(?<="id":)[0-9]+' | head -1 || echo "")
+
+          if [ -z "$TAG_ID" ]; then
+            echo "Tag may already exist, looking it up..."
+            TAG_ID=$(curl -s -u admin:admin \
+              -X PROPFIND \
+              -H 'Content-Type: application/xml' \
+              -d '<?xml version="1.0"?><d:propfind xmlns:d="DAV:" xmlns:oc="http://owncloud.org/ns"><d:prop><oc:id/><oc:display-name/></d:prop></d:propfind>' \
+              http://localhost:8080/remote.php/dav/systemtags/ \
+              | grep -B2 "vector-index" | grep -oP '(?<=<oc:id>)[0-9]+(?=</oc:id>)' | head -1 || echo "")
+          fi
+
+          if [ -z "$TAG_ID" ]; then
+            echo "ERROR: Could not create or find vector-index tag"
+            exit 1
+          fi
+
+          echo "Tag ID: $TAG_ID"
+          echo "tag_id=$TAG_ID" >> $GITHUB_OUTPUT
+
+      - name: Get file ID of uploaded PDF
+        id: get_file_id
+        run: |
+          echo "Getting file ID for Nextcloud_User_Manual.pdf..."
+
+          # Get file ID using PROPFIND
+          FILE_ID=$(curl -s -u admin:admin \
+            -X PROPFIND \
+            -H 'Content-Type: application/xml' \
+            -d '<?xml version="1.0"?><d:propfind xmlns:d="DAV:" xmlns:oc="http://owncloud.org/ns"><d:prop><oc:fileid/></d:prop></d:propfind>' \
+            "http://localhost:8080/remote.php/dav/files/admin/Nextcloud_User_Manual.pdf" \
+            | grep -oP '(?<=<oc:fileid>)[0-9]+(?=</oc:fileid>)' || echo "")
+
+          if [ -z "$FILE_ID" ]; then
+            echo "ERROR: Could not find file ID"
+            exit 1
+          fi
+
+          echo "Found file ID: $FILE_ID"
+          echo "file_id=$FILE_ID" >> $GITHUB_OUTPUT
+
+      - name: Tag file with vector-index
+        env:
+          FILE_ID: ${{ steps.get_file_id.outputs.file_id }}
+          TAG_ID: ${{ steps.create_tag.outputs.tag_id }}
+        run: |
+          echo "Tagging file $FILE_ID with tag $TAG_ID..."
+
+          HTTP_CODE=$(curl -s -o /dev/null -w "%{http_code}" -u admin:admin \
+            -X PUT \
+            -H 'Content-Type: application/json' \
+            -H 'Content-Length: 0' \
+            "http://localhost:8080/remote.php/dav/systemtags-relations/files/$FILE_ID/$TAG_ID")
+
+          if [ "$HTTP_CODE" = "201" ] || [ "$HTTP_CODE" = "409" ]; then
+            echo "File tagged successfully (HTTP $HTTP_CODE)"
+          else
+            echo "Failed to tag file (HTTP $HTTP_CODE)"
+            exit 1
+          fi
+
+      - name: Wait for vector sync to complete indexing
+        env:
+          NEXTCLOUD_HOST: "http://localhost:8080"
+          NEXTCLOUD_USERNAME: "admin"
+          NEXTCLOUD_PASSWORD: "admin"
+        run: |
+          echo "Waiting for vector sync to index the manual..."
+          max_attempts=60
+          attempt=0
+
+          # Wait for initial scan to pick up the file
+          sleep 10
+
+          while [ $attempt -lt $max_attempts ]; do
+            attempt=$((attempt + 1))
+
+            # Check vector sync status via MCP
+            STATUS=$(curl -s http://localhost:8000/health || echo "{}")
+            echo "Attempt $attempt/$max_attempts: $STATUS"
+
+            # Also check indexed count via semantic search
+            # If we get results, indexing is done
+            RESULT=$(curl -s -X POST http://localhost:8000/mcp \
+              -H "Content-Type: application/json" \
+              -d '{"jsonrpc":"2.0","id":1,"method":"tools/call","params":{"name":"nc_get_vector_sync_status","arguments":{}}}' \
+              2>/dev/null || echo "{}")
+
+            echo "Vector sync status: $RESULT"
+
+            # Check if pending is 0 and indexed > 0
+            INDEXED=$(echo "$RESULT" | jq -r '.result.structuredContent.indexed // 0' 2>/dev/null || echo "0")
+            PENDING=$(echo "$RESULT" | jq -r '.result.structuredContent.pending // 1' 2>/dev/null || echo "1")
+
+            echo "Indexed: $INDEXED, Pending: $PENDING"
+
+            if [ "$INDEXED" -gt "0" ] && [ "$PENDING" -eq "0" ]; then
+              echo "Indexing complete! $INDEXED documents indexed."
+              break
+            fi
+
+            sleep 10
+          done
+
+          if [ $attempt -ge $max_attempts ]; then
+            echo "WARNING: Indexing may not be complete, proceeding anyway..."
+          fi
+
+      - name: Run RAG evaluation tests
+        env:
+          NEXTCLOUD_HOST: "http://localhost:8080"
+          NEXTCLOUD_USERNAME: "admin"
+          NEXTCLOUD_PASSWORD: "admin"
+          OPENAI_API_KEY: ${{ secrets.GITHUB_TOKEN }}
+          OPENAI_BASE_URL: "https://models.github.ai/inference"
+          OPENAI_EMBEDDING_MODEL: ${{ inputs.embedding_model }}
+          OPENAI_GENERATION_MODEL: ${{ inputs.generation_model }}
+        run: |
+          uv run pytest tests/integration/test_rag_openai.py -v --log-cli-level=INFO
+
+      - name: Upload test results
+        if: always()
+        uses: actions/upload-artifact@v4
+        with:
+          name: rag-evaluation-results
+          path: |
+            pytest-results.xml
+          retention-days: 30