feat: implement automatic ChromaDB indexing and loop-based documentation generation

- Add automatic ChromaDB indexing after documentation generation
- Implement loop-based section generation for individual VM and container documentation
- Fix Celery anti-pattern in generate_proxmox_docs task (removed blocking .get() call)
- Share ChromaDB vector store volume between worker and chat services
- Add documentation management UI to frontend with manual job triggering and log viewing
- Fix frontend Socket.IO connection URL to point to correct chat service port
- Enhance DocumentationAgent.index_documentation() with automatic cleanup of old documents
- Update Proxmox template to generate individual files for each VM and container

This enables the RAG system to properly respond with infrastructure-specific information from the generated documentation.

🤖 Generated with [Claude Code](https://claude.com/claude-code)

Co-Authored-By: Claude <noreply@anthropic.com>

deploy/docker/Dockerfile.worker

@@ -39,6 +39,7 @@ RUN pip install --no-cache-dir -r requirements.txt
 # Copy application code and package definition
 COPY src/ /app/src/
 COPY config/ /app/config/
+COPY templates/ /app/templates/
 COPY pyproject.toml README.md /app/
 
 # Install poetry-core (required for install with pyproject.toml)
@@ -59,5 +60,5 @@ RUN useradd -m -u 1000 appuser && \
 
 USER appuser
 
-# Run the Celery worker
+# Run the Celery worker with specific queues
-CMD ["celery", "-A", "datacenter_docs.workers.celery_app", "worker", "--loglevel=info", "--concurrency=4"]
+CMD ["celery", "-A", "datacenter_docs.workers.celery_app", "worker", "--loglevel=info", "--concurrency=4", "-Q", "documentation,auto_remediation,data_collection,maintenance,celery"]

deploy/docker/docker-compose.dev.yml

@@ -58,7 +58,8 @@ services:
       - ../../src:/app/src
       - ../../config:/app/config
       - api-logs:/app/logs
-      - api-output:/app/output
+      - worker-output:/app/output  # Shared with worker for documentation files
+      - /var/run/docker.sock:/var/run/docker.sock:ro  # For accessing worker logs
     depends_on:
       mongodb:
         condition: service_healthy
@@ -82,7 +83,7 @@ services:
     volumes:
       - ../../src:/app/src:z
       - ../../config:/app/config:z
-      - ../../output:/app/output:z  # Documentation files
+      - worker-output:/app/output  # Shared documentation files with worker
       - ../../scripts:/app/scripts:z  # Indexing scripts
       - chat-logs:/app/logs
       - chat-data:/app/data  # Vector store persistence
@@ -109,6 +110,7 @@ services:
       - ../../config:/app/config
       - worker-logs:/app/logs
       - worker-output:/app/output
+      - chat-data:/app/data  # Shared ChromaDB vector store with chat
     depends_on:
       mongodb:
         condition: service_healthy
@@ -163,8 +165,6 @@ volumes:
     name: datacenter-docs-redis-data-dev
   api-logs:
     name: datacenter-docs-api-logs-dev
-  api-output:
-    name: datacenter-docs-api-output-dev
   chat-logs:
     name: datacenter-docs-chat-logs-dev
   chat-data:

frontend/src/App.jsx

@@ -21,7 +21,7 @@ import remarkGfm from 'remark-gfm';
 
 // Use relative URLs to work with nginx proxy in production
 const API_URL = import.meta.env.VITE_API_URL || (typeof window !== 'undefined' ? window.location.origin + '/api' : 'http://localhost:8000');
-const CHAT_URL = import.meta.env.VITE_CHAT_URL || (typeof window !== 'undefined' ? window.location.origin : 'http://localhost:8001');
+const CHAT_URL = import.meta.env.VITE_CHAT_URL || 'http://localhost:8001';
 
 function App() {
   const [activeTab, setActiveTab] = useState(0);
@@ -43,6 +43,7 @@ function App() {
           <Tab label="Chat Support" />
           <Tab label="Ticket Resolution" />
           <Tab label="Documentation Search" />
+          <Tab label="Documentation Management" />
         </Tabs>
       </Box>
 
@@ -50,6 +51,7 @@ function App() {
         {activeTab === 0 && <ChatInterface />}
         {activeTab === 1 && <TicketInterface />}
         {activeTab === 2 && <SearchInterface />}
+        {activeTab === 3 && <DocumentationInterface />}
       </Container>
     </Box>
   );
@@ -441,4 +443,302 @@ function SearchInterface() {
   );
 }
 
+// Documentation Management Interface
+function DocumentationInterface() {
+  const [jobStatus, setJobStatus] = useState(null);
+  const [generatingJob, setGeneratingJob] = useState(null);
+  const [files, setFiles] = useState([]);
+  const [selectedFile, setSelectedFile] = useState(null);
+  const [fileContent, setFileContent] = useState(null);
+  const [loading, setLoading] = useState(false);
+  const [showLogs, setShowLogs] = useState(false);
+  const [jobLogs, setJobLogs] = useState([]);
+
+  // Load available files on mount
+  useEffect(() => {
+    loadFiles();
+  }, []);
+
+  // Poll job status when generating
+  useEffect(() => {
+    if (!generatingJob) return;
+
+    const pollInterval = setInterval(async () => {
+      try {
+        const response = await axios.get(`${API_URL}/api/v1/documentation/jobs/${generatingJob}/status`);
+        setJobStatus(response.data);
+
+        if (response.data.completed) {
+          clearInterval(pollInterval);
+          setGeneratingJob(null);
+          loadFiles(); // Refresh file list
+        }
+      } catch (error) {
+        console.error('Error polling job status:', error);
+        clearInterval(pollInterval);
+        setGeneratingJob(null);
+      }
+    }, 2000);
+
+    return () => clearInterval(pollInterval);
+  }, [generatingJob]);
+
+  // Poll logs when log viewer is open
+  useEffect(() => {
+    if (!showLogs || !jobStatus?.job_id) return;
+
+    const loadLogs = async () => {
+      try {
+        const response = await axios.get(`${API_URL}/api/v1/documentation/jobs/${jobStatus.job_id}/logs`);
+        setJobLogs(response.data.logs || []);
+      } catch (error) {
+        console.error('Error loading logs:', error);
+      }
+    };
+
+    loadLogs(); // Initial load
+    const logInterval = setInterval(loadLogs, 3000); // Poll every 3 seconds
+
+    return () => clearInterval(logInterval);
+  }, [showLogs, jobStatus?.job_id]);
+
+  const loadFiles = async () => {
+    try {
+      const response = await axios.get(`${API_URL}/api/v1/documentation/files`);
+      setFiles(response.data.categories || []);
+    } catch (error) {
+      console.error('Error loading files:', error);
+    }
+  };
+
+  const triggerGeneration = async () => {
+    setLoading(true);
+    setJobStatus(null);
+    try {
+      const response = await axios.post(`${API_URL}/api/v1/documentation/jobs/proxmox`);
+      setGeneratingJob(response.data.job_id);
+      setJobStatus({
+        job_id: response.data.job_id,
+        status: response.data.status,
+        completed: false
+      });
+    } catch (error) {
+      console.error('Error triggering generation:', error);
+      alert('Failed to start documentation generation: ' + error.message);
+    }
+    setLoading(false);
+  };
+
+  const viewFile = async (category, filename) => {
+    setLoading(true);
+    try {
+      const response = await axios.get(`${API_URL}/api/v1/documentation/files/${category}/${filename}`);
+      setFileContent(response.data);
+      setSelectedFile({ category, filename });
+    } catch (error) {
+      console.error('Error loading file:', error);
+      alert('Failed to load file: ' + error.message);
+    }
+    setLoading(false);
+  };
+
+  const formatBytes = (bytes) => {
+    if (bytes < 1024) return bytes + ' B';
+    if (bytes < 1024 * 1024) return (bytes / 1024).toFixed(1) + ' KB';
+    return (bytes / (1024 * 1024)).toFixed(1) + ' MB';
+  };
+
+  const formatDate = (timestamp) => {
+    return new Date(timestamp * 1000).toLocaleString();
+  };
+
+  return (
+    <Grid container spacing={3}>
+      {/* Control Panel */}
+      <Grid item xs={12} md={4}>
+        <Paper sx={{ p: 3, mb: 2 }}>
+          <Typography variant="h6" gutterBottom>Generate Documentation</Typography>
+          <Typography variant="body2" color="text.secondary" paragraph>
+            Trigger manual generation of Proxmox infrastructure documentation
+          </Typography>
+          <Button
+            fullWidth
+            variant="contained"
+            onClick={triggerGeneration}
+            disabled={loading || generatingJob}
+            startIcon={<UploadIcon />}
+            sx={{ mb: 2 }}
+          >
+            {generatingJob ? 'Generating...' : 'Generate Proxmox Docs'}
+          </Button>
+
+          {jobStatus && (
+            <Box sx={{ mt: 2 }}>
+              <Typography variant="subtitle2" gutterBottom>Job Status</Typography>
+              <Box sx={{ display: 'flex', alignItems: 'center', gap: 1, mb: 1 }}>
+                {!jobStatus.completed && <CircularProgress size={20} />}
+                <Chip
+                  label={jobStatus.status}
+                  color={jobStatus.completed ? (jobStatus.status === 'SUCCESS' ? 'success' : 'error') : 'warning'}
+                  size="small"
+                />
+              </Box>
+              <Typography variant="caption" color="text.secondary" display="block">
+                Job ID: {jobStatus.job_id}
+              </Typography>
+              <Button
+                size="small"
+                variant="outlined"
+                onClick={() => setShowLogs(!showLogs)}
+                sx={{ mt: 1 }}
+                fullWidth
+              >
+                {showLogs ? 'Hide Logs' : 'View Logs'}
+              </Button>
+              {jobStatus.error && (
+                <Typography variant="caption" color="error" display="block" sx={{ mt: 1 }}>
+                  Error: {jobStatus.error}
+                </Typography>
+              )}
+            </Box>
+          )}
+        </Paper>
+
+        {/* Log Viewer */}
+        {showLogs && jobStatus && (
+          <Paper sx={{ p: 2, mb: 2, bgcolor: '#1e1e1e', maxHeight: '400px', overflow: 'auto' }}>
+            <Typography variant="subtitle2" gutterBottom sx={{ color: '#fff' }}>
+              Job Logs (Last 50 lines)
+            </Typography>
+            {jobLogs.length === 0 ? (
+              <Typography variant="caption" sx={{ color: '#888' }}>
+                No logs available yet...
+              </Typography>
+            ) : (
+              <Box component="pre" sx={{
+                fontFamily: 'monospace',
+                fontSize: '0.75rem',
+                color: '#0f0',
+                margin: 0,
+                whiteSpace: 'pre-wrap',
+                wordBreak: 'break-all'
+              }}>
+                {jobLogs.join('\n')}
+              </Box>
+            )}
+          </Paper>
+        )}
+
+        {/* File List */}
+        <Paper sx={{ p: 2 }}>
+          <Typography variant="h6" gutterBottom>Available Documentation</Typography>
+          {files.length === 0 ? (
+            <Typography variant="body2" color="text.secondary">
+              No documentation files found. Generate some first!
+            </Typography>
+          ) : (
+            files.map((category) => (
+              <Box key={category.name} sx={{ mb: 2 }}>
+                <Typography variant="subtitle2" sx={{ mb: 1, fontWeight: 'bold' }}>
+                  {category.name.toUpperCase()}
+                </Typography>
+                <List dense>
+                  {category.files.map((file) => (
+                    <ListItem
+                      key={file.filename}
+                      button
+                      onClick={() => viewFile(category.name, file.filename)}
+                      selected={selectedFile?.filename === file.filename}
+                    >
+                      <ListItemText
+                        primary={file.filename}
+                        secondary={`${formatBytes(file.size)} • ${formatDate(file.modified)}`}
+                      />
+                    </ListItem>
+                  ))}
+                </List>
+              </Box>
+            ))
+          )}
+        </Paper>
+      </Grid>
+
+      {/* Markdown Viewer */}
+      <Grid item xs={12} md={8}>
+        {fileContent ? (
+          <Paper sx={{ p: 3 }}>
+            <Box sx={{ display: 'flex', justifyContent: 'space-between', alignItems: 'center', mb: 2 }}>
+              <Typography variant="h6">{fileContent.filename}</Typography>
+              <Chip label={fileContent.category} size="small" />
+            </Box>
+            <Divider sx={{ mb: 3 }} />
+            <Box sx={{
+              '& h1, & h2, & h3': { mt: 3, mb: 2 },
+              '& h1': { fontSize: '2rem', fontWeight: 600, borderBottom: '2px solid #e0e0e0', pb: 1 },
+              '& h2': { fontSize: '1.5rem', fontWeight: 600 },
+              '& h3': { fontSize: '1.2rem', fontWeight: 600 },
+              '& p': { mb: 2, lineHeight: 1.6 },
+              '& ul, & ol': { pl: 3, mb: 2 },
+              '& li': { mb: 1 },
+              '& code': {
+                bgcolor: '#f5f5f5',
+                p: 0.5,
+                borderRadius: 1,
+                fontFamily: 'monospace',
+                fontSize: '0.9em',
+                border: '1px solid #e0e0e0'
+              },
+              '& pre': {
+                bgcolor: '#f5f5f5',
+                p: 2,
+                borderRadius: 1,
+                overflow: 'auto',
+                border: '1px solid #e0e0e0',
+                '& code': { bgcolor: 'transparent', p: 0, border: 'none' }
+              },
+              '& table': {
+                width: '100%',
+                borderCollapse: 'collapse',
+                mb: 2
+              },
+              '& th, & td': {
+                border: '1px solid #e0e0e0',
+                p: 1,
+                textAlign: 'left'
+              },
+              '& th': {
+                bgcolor: '#f5f5f5',
+                fontWeight: 600
+              },
+              '& blockquote': {
+                borderLeft: '4px solid #e0e0e0',
+                pl: 2,
+                ml: 0,
+                fontStyle: 'italic',
+                color: 'text.secondary'
+              },
+              '& hr': { my: 3, border: 'none', borderTop: '1px solid #e0e0e0' }
+            }}>
+              <ReactMarkdown remarkPlugins={[remarkGfm]}>
+                {fileContent.content}
+              </ReactMarkdown>
+            </Box>
+            <Divider sx={{ mt: 3, mb: 2 }} />
+            <Typography variant="caption" color="text.secondary">
+              Last modified: {formatDate(fileContent.modified)} • Size: {formatBytes(fileContent.size)}
+            </Typography>
+          </Paper>
+        ) : (
+          <Paper sx={{ p: 3, textAlign: 'center' }}>
+            <DocIcon sx={{ fontSize: 64, color: 'text.secondary', mb: 2 }} />
+            <Typography variant="h6" color="text.secondary">
+              Select a documentation file to view
+            </Typography>
+          </Paper>
+        )}
+      </Grid>
+    </Grid>
+  );
+}
+
 export default App;

src/datacenter_docs/api/main.py

@@ -339,6 +339,220 @@ async def list_sections() -> Dict[str, Any]:
     }
 
 
+# Documentation Jobs API
+@app.post("/api/v1/documentation/jobs/proxmox")
+async def trigger_proxmox_documentation() -> Dict[str, Any]:
+    """
+    Trigger Proxmox documentation generation job
+
+    Returns job_id for status monitoring
+    """
+    from celery import Celery
+    from datacenter_docs.utils.config import get_settings
+
+    try:
+        settings = get_settings()
+
+        # Create minimal Celery client for sending tasks
+        celery_client = Celery(
+            "datacenter_docs",
+            broker=settings.CELERY_BROKER_URL,
+            backend=settings.CELERY_RESULT_BACKEND,
+        )
+
+        # Send task by name to the documentation queue
+        task = celery_client.send_task(
+            "generate_proxmox_docs",
+            kwargs={},
+            queue="documentation",
+        )
+
+        logger.info(f"Triggered Proxmox docs generation job: {task.id}")
+
+        return {
+            "success": True,
+            "job_id": task.id,
+            "status": "queued",
+            "message": "Proxmox documentation generation job started",
+        }
+    except Exception as e:
+        logger.error(f"Failed to trigger Proxmox docs job: {e}", exc_info=True)
+        raise HTTPException(status_code=500, detail=f"Failed to start job: {str(e)}")
+
+
+@app.get("/api/v1/documentation/jobs/{job_id}/status")
+async def get_job_status(job_id: str) -> Dict[str, Any]:
+    """
+    Get status of documentation generation job
+
+    Returns current status and progress information
+    """
+    from celery.result import AsyncResult
+    from datacenter_docs.workers.celery_app import celery_app
+
+    try:
+        result = AsyncResult(job_id, app=celery_app)
+
+        response = {
+            "job_id": job_id,
+            "status": result.state,  # PENDING, STARTED, SUCCESS, FAILURE, RETRY
+        }
+
+        if result.state == "SUCCESS":
+            response["result"] = result.result
+            response["completed"] = True
+        elif result.state == "FAILURE":
+            response["error"] = str(result.info)
+            response["completed"] = True
+        elif result.state == "PROGRESS":
+            response["progress"] = result.info
+            response["completed"] = False
+        else:
+            response["completed"] = False
+
+        return response
+
+    except Exception as e:
+        logger.error(f"Failed to get job status: {e}")
+        raise HTTPException(status_code=500, detail=f"Failed to get status: {str(e)}")
+
+
+@app.get("/api/v1/documentation/files")
+async def list_documentation_files() -> Dict[str, Any]:
+    """
+    List all generated documentation files
+
+    Returns available markdown files organized by category
+    """
+    from pathlib import Path
+
+    output_dir = Path("/app/output")
+
+    if not output_dir.exists():
+        return {"categories": [], "total": 0}
+
+    files_by_category = {}
+
+    # Scan output directory
+    for category_dir in output_dir.iterdir():
+        if category_dir.is_dir():
+            category = category_dir.name
+            files = []
+
+            for file_path in category_dir.glob("*.md"):
+                stat = file_path.stat()
+                files.append({
+                    "filename": file_path.name,
+                    "size": stat.st_size,
+                    "modified": stat.st_mtime,
+                    "path": f"{category}/{file_path.name}"
+                })
+
+            if files:
+                files_by_category[category] = sorted(files, key=lambda x: x["modified"], reverse=True)
+
+    total_files = sum(len(files) for files in files_by_category.values())
+
+    return {
+        "categories": [
+            {"name": cat, "files": files}
+            for cat, files in files_by_category.items()
+        ],
+        "total": total_files
+    }
+
+
+@app.get("/api/v1/documentation/files/{category}/{filename}")
+async def get_documentation_content(category: str, filename: str) -> Dict[str, Any]:
+    """
+    Retrieve content of a specific documentation file
+
+    Returns markdown content
+    """
+    from pathlib import Path
+
+    # Validate filename to prevent directory traversal
+    if ".." in filename or "/" in filename:
+        raise HTTPException(status_code=400, detail="Invalid filename")
+
+    if ".." in category or "/" in category:
+        raise HTTPException(status_code=400, detail="Invalid category")
+
+    file_path = Path(f"/app/output/{category}/{filename}")
+
+    if not file_path.exists():
+        raise HTTPException(status_code=404, detail="Documentation file not found")
+
+    if not file_path.is_file() or file_path.suffix != ".md":
+        raise HTTPException(status_code=400, detail="Invalid file type")
+
+    try:
+        content = file_path.read_text(encoding="utf-8")
+        stat = file_path.stat()
+
+        return {
+            "filename": filename,
+            "category": category,
+            "content": content,
+            "size": stat.st_size,
+            "modified": stat.st_mtime
+        }
+    except Exception as e:
+        logger.error(f"Failed to read file {file_path}: {e}")
+        raise HTTPException(status_code=500, detail=f"Failed to read file: {str(e)}")
+
+
+@app.get("/api/v1/documentation/jobs/{job_id}/logs")
+async def get_job_logs(job_id: str, tail: int = 100) -> Dict[str, Any]:
+    """
+    Get logs for a specific documentation generation job
+
+    Returns recent log lines related to the job
+    """
+    import subprocess
+
+    try:
+        # Get worker logs and filter for job_id
+        cmd = [
+            "docker",
+            "logs",
+            "datacenter-docs-worker-dev",
+            "--tail",
+            str(tail)
+        ]
+
+        result = subprocess.run(
+            cmd,
+            capture_output=True,
+            text=True,
+            timeout=5
+        )
+
+        all_logs = result.stdout + result.stderr
+
+        # Filter logs containing the job_id
+        job_logs = [
+            line
+            for line in all_logs.split("\n")
+            if job_id in line or "ForkPoolWorker" in line
+        ]
+
+        # Take last 50 relevant lines
+        relevant_logs = job_logs[-50:] if len(job_logs) > 50 else job_logs
+
+        return {
+            "job_id": job_id,
+            "logs": relevant_logs,
+            "total_lines": len(relevant_logs)
+        }
+
+    except subprocess.TimeoutExpired:
+        raise HTTPException(status_code=504, detail="Timeout getting logs")
+    except Exception as e:
+        logger.error(f"Failed to get job logs: {e}")
+        raise HTTPException(status_code=500, detail=f"Failed to get logs: {str(e)}")
+
+
 # Stats and Metrics
 @app.get("/api/v1/stats/tickets")
 async def get_ticket_stats() -> Dict[str, Any]:

src/datacenter_docs/chat/agent.py

@@ -76,21 +76,43 @@ class DocumentationAgent:
 
     async def index_documentation(self, docs_path: Path) -> None:
         """Index all documentation files into vector store"""
-        logger.info("Indexing documentation...")
+        logger.info("📚 Indexing documentation...")
+
+        # Clear existing documents to avoid duplicates
+        if self.vector_store is not None:
+            try:
+                # Delete the collection and recreate it
+                logger.info("🗑️  Clearing old documentation from vector store...")
+                self.vector_store.delete_collection()
+                self.vector_store = Chroma(
+                    persist_directory=str(self.vector_store_path),
+                    embedding_function=self.embeddings,
+                )
+                logger.info("✅ Vector store cleared and recreated")
+            except Exception as e:
+                logger.warning(f"⚠️  Could not clear vector store (might be first run): {e}")
 
         documents = []
+        files_processed = 0
 
         # Read all markdown files
         for md_file in docs_path.glob("**/*.md"):
+            try:
                 with open(md_file, "r", encoding="utf-8") as f:
                     content = f.read()
 
+                # Skip empty files
+                if not content.strip():
+                    logger.warning(f"⚠️  Skipping empty file: {md_file}")
+                    continue
+
                 # Split into chunks
                 splitter = RecursiveCharacterTextSplitter(
                     chunk_size=1000, chunk_overlap=200, length_function=len
                 )
 
                 chunks = splitter.split_text(content)
+                files_processed += 1
 
                 for i, chunk in enumerate(chunks):
                     doc = Document(
@@ -104,12 +126,19 @@ class DocumentationAgent:
                     )
                     documents.append(doc)
 
+                logger.info(f"  ✓ Indexed {md_file.name} ({len(chunks)} chunks)")
+
+            except Exception as e:
+                logger.error(f"❌ Failed to index {md_file}: {e}")
+
         # Add to vector store
-        if self.vector_store is not None:
+        if self.vector_store is not None and documents:
+            logger.info(f"💾 Adding {len(documents)} chunks to vector store...")
             self.vector_store.add_documents(documents)
             self.vector_store.persist()
-
+            logger.info(f"✅ Indexed {files_processed} files ({len(documents)} chunks) from documentation")
-        logger.info(f"Indexed {len(documents)} chunks from documentation")
+        else:
+            logger.warning("⚠️  No documents to index")
 
     async def search_documentation(
         self, query: str, sections: Optional[List[str]] = None, limit: int = 5

src/datacenter_docs/generators/template_generator.py

@@ -240,12 +240,15 @@ Guidelines:
 
         return prompt
 
-    def _format_data_for_prompt(self, data: Any) -> str:
+    def _format_data_for_prompt(self, data: Any, max_items: int = 10) -> str:
         """
         Format data for inclusion in LLM prompt
 
+        For large datasets, limits the number of items to prevent overwhelming small LLMs.
+
         Args:
             data: Data to format (dict, list, str, etc.)
+            max_items: Maximum number of items to include for lists (default: 10)
 
         Returns:
             Formatted string representation
@@ -253,7 +256,24 @@ Guidelines:
         if data is None:
             return "No data available"
 
-        if isinstance(data, (dict, list)):
+        if isinstance(data, list):
+            # Limit list size for small LLMs
+            total_count = len(data)
+            if total_count > max_items:
+                limited_data = data[:max_items]
+                try:
+                    formatted = json.dumps(limited_data, indent=2, default=str)
+                    summary = f"\n\n**Note: Showing {max_items} of {total_count} items. Full count: {total_count}**\n"
+                    return formatted + summary
+                except Exception:
+                    return str(limited_data) + summary
+            # Small list, show all
+            try:
+                return json.dumps(data, indent=2, default=str)
+            except Exception:
+                return str(data)
+
+        if isinstance(data, dict):
             # Pretty print JSON for structured data
             try:
                 return json.dumps(data, indent=2, default=str)
@@ -305,12 +325,15 @@ Guidelines:
         This is useful for very large documentation where you want each
         section as a separate file.
 
+        Supports looped sections where one section definition generates
+        multiple output files (e.g., one file per VM).
+
         Args:
             data: Collected infrastructure data
             save_individually: Save each section as separate file
 
         Returns:
-            List of results for each section
+            List of results for each section (may be multiple for looped sections)
         """
         results = []
         output_config = self.template.output_config
@@ -322,6 +345,17 @@ Guidelines:
             section_id = section_def.get("id")
             section_title = section_def.get("title")
 
+            # Check if this section should loop over items
+            loop_over = section_def.get("loop_over")
+
+            if loop_over:
+                # Generate one section per item in the loop
+                loop_results = await self._generate_looped_sections(
+                    section_def, data, output_dir, save_to_db, save_to_file, save_individually
+                )
+                results.extend(loop_results)
+            else:
+                # Generate single section (original behavior)
                 # Generate section
                 content = await self.generate_section(section_def, data)
 
@@ -355,24 +389,207 @@ Guidelines:
                         self.logger.info(f"Saved section to: {file_path}")
 
                     if save_to_db:
-                    # Save to database
+                        # Save to database using our own instance
                         metadata = {
                             "section_id": section_id,
                             "template": str(self.template.path),
                             "category": section_def.get("category", ""),
                         }
-                    # Create temporary generator for this section
+                        # Use current instance with modified section name
-                    temp_gen = BaseGenerator.__new__(BaseGenerator)
+                        original_section = self.section
-                    temp_gen.name = self.name
+                        self.section = section_id
-                    temp_gen.section = section_id
+                        try:
-                    temp_gen.logger = self.logger
+                            await self.save_to_database(content, metadata)
-                    temp_gen.llm = self.llm
+                        finally:
-                    await temp_gen.save_to_database(content, metadata)
+                            # Restore original section name
+                            self.section = original_section
 
                 results.append(result)
 
         return results
 
+    async def _generate_looped_sections(
+        self,
+        section_def: Dict[str, Any],
+        full_data: Dict[str, Any],
+        output_dir: str,
+        save_to_db: bool,
+        save_to_file: bool,
+        save_individually: bool,
+    ) -> List[Dict[str, Any]]:
+        """
+        Generate multiple sections by looping over items
+
+        Args:
+            section_def: Section definition with loop_over key
+            full_data: Complete collected data
+            output_dir: Output directory
+            save_to_db: Whether to save to database
+            save_to_file: Whether to save to file
+            save_individually: Whether to save each item individually
+
+        Returns:
+            List of results, one per looped item
+        """
+        results = []
+        section_id = section_def.get("id")
+        loop_over = section_def.get("loop_over")
+        loop_item_name = section_def.get("loop_item_name", "item")
+
+        # Get the data to loop over
+        data_section = full_data.get("data", {})
+        items = data_section.get(loop_over, [])
+
+        if not isinstance(items, list):
+            self.logger.warning(f"loop_over '{loop_over}' is not a list, skipping")
+            return []
+
+        total_items = len(items)
+        self.logger.info(f"Looping over {total_items} {loop_over} to generate individual sections")
+
+        # Generate one section per item
+        for idx, item in enumerate(items, 1):
+            try:
+                # Create item-specific section definition
+                item_section_def = section_def.copy()
+
+                # Get item identifier for filename
+                item_id = item.get("vmid") or item.get("id") or item.get("name") or f"item_{idx}"
+                item_name = item.get("name", f"{loop_over}_{item_id}")
+
+                # Build item-specific data context
+                item_data = self._build_item_context(section_def, full_data, item, loop_item_name)
+
+                # Build prompt with item context
+                prompt_template = item_section_def.get("prompt_template", "")
+                prompt = self._build_prompt(prompt_template, item_data)
+
+                # Get generation config
+                gen_config = self.template.generation_config
+                temperature = gen_config.get("temperature", 0.7)
+                max_tokens = gen_config.get("max_tokens", 4000)
+
+                # System prompt
+                system_prompt = """You are a technical documentation expert specializing in datacenter infrastructure.
+Generate clear, accurate, and well-structured documentation in Markdown format.
+
+Guidelines:
+- Use proper Markdown formatting (headers, tables, lists, code blocks)
+- Be precise and factual based on provided data
+- Include practical examples and recommendations
+- Use tables for structured data
+- Use bullet points for lists
+- Use code blocks for commands/configurations
+- Organize content with clear sections
+- Write in a professional but accessible tone
+"""
+
+                # Generate content
+                content = await self.generate_with_llm(
+                    system_prompt=system_prompt,
+                    user_prompt=prompt,
+                    temperature=temperature,
+                    max_tokens=max_tokens,
+                )
+
+                # Create title with item name
+                # Support both {item_name} and {loop_item_name}_{name} patterns
+                title_template = item_section_def.get("title", "")
+                title_context = {
+                    loop_item_name: item_name,
+                    f"{loop_item_name}_name": item_name,
+                    f"{loop_item_name}_id": str(item_id),
+                }
+                section_title = title_template.format(**title_context)
+                section_content = f"# {section_title}\n\n{content}\n\n"
+
+                result = {
+                    "section_id": f"{section_id}_{item_id}",
+                    "title": section_title,
+                    "success": True,
+                    "content": section_content,
+                    "item_index": idx,
+                    "total_items": total_items,
+                }
+
+                # Save if requested
+                if save_individually:
+                    if save_to_file:
+                        output_path = Path(output_dir)
+                        output_path.mkdir(parents=True, exist_ok=True)
+                        # Use category subdirectory if specified
+                        category = section_def.get("category", "")
+                        if category:
+                            output_path = output_path / category
+                            output_path.mkdir(parents=True, exist_ok=True)
+
+                        filename = f"{section_id}_{item_id}.md"
+                        file_path = output_path / filename
+                        file_path.write_text(section_content, encoding="utf-8")
+                        result["file_path"] = str(file_path)
+                        self.logger.info(f"[{idx}/{total_items}] Saved: {file_path}")
+
+                    if save_to_db:
+                        metadata = {
+                            "section_id": f"{section_id}_{item_id}",
+                            "template": str(self.template.path),
+                            "category": section_def.get("category", ""),
+                            "item_id": str(item_id),
+                            "item_name": item_name,
+                        }
+                        original_section = self.section
+                        self.section = f"{section_id}_{item_id}"
+                        try:
+                            await self.save_to_database(section_content, metadata)
+                        finally:
+                            self.section = original_section
+
+                results.append(result)
+                self.logger.info(f"✓ [{idx}/{total_items}] Generated: {section_title}")
+
+            except Exception as e:
+                self.logger.error(f"Failed to generate section for {loop_over} item {idx}: {e}")
+                results.append({
+                    "section_id": f"{section_id}_item_{idx}",
+                    "success": False,
+                    "error": str(e),
+                    "item_index": idx,
+                    "total_items": total_items,
+                })
+
+        return results
+
+    def _build_item_context(
+        self,
+        section_def: Dict[str, Any],
+        full_data: Dict[str, Any],
+        item: Dict[str, Any],
+        loop_item_name: str,
+    ) -> Dict[str, Any]:
+        """
+        Build data context for a looped item
+
+        Args:
+            section_def: Section definition
+            full_data: Complete collected data
+            item: Current loop item
+            loop_item_name: Variable name for the item in prompt
+
+        Returns:
+            Dictionary with item and any additional required data
+        """
+        context = {loop_item_name: item}
+
+        # Add any additional required data from section definition
+        data_requirements = section_def.get("data_requirements", [])
+        data_section = full_data.get("data", {})
+
+        for req in data_requirements:
+            if req in data_section:
+                context[req] = data_section[req]
+
+        return context
+
 
 async def example_usage() -> None:
     """Example of using template-based generator"""

src/datacenter_docs/utils/llm_client.py

@@ -81,7 +81,8 @@ class LLMClient:
         self.max_tokens = max_tokens or settings.LLM_MAX_TOKENS
 
         # Initialize AsyncOpenAI client with custom HTTP client (disable SSL verification for self-signed certs)
-        http_client = httpx.AsyncClient(verify=False, timeout=30.0)
+        # Increased timeout to 120s for documentation generation (large prompts)
+        http_client = httpx.AsyncClient(verify=False, timeout=120.0)
         self.client = AsyncOpenAI(
             base_url=self.base_url,
             api_key=self.api_key,
@@ -129,6 +130,13 @@ class LLMClient:
             # Type guard: we know it's ChatCompletion when stream=False
             response = cast(ChatCompletion, response)
 
+            # Check for None response or empty choices
+            if response is None:
+                raise ValueError("LLM returned None response")
+
+            if not response.choices or len(response.choices) == 0:
+                raise ValueError("LLM returned empty choices")
+
             # Extract text from first choice
             message = response.choices[0].message
             content = message.content or ""

src/datacenter_docs/workers/documentation_tasks.py

@@ -94,6 +94,7 @@ async def _async_collect_and_generate(
         Generation result
     """
     from datacenter_docs.generators.template_generator import TemplateBasedGenerator
+    from datacenter_docs.chat.agent import DocumentationAgent
 
     # Import appropriate collector
     collector = await _get_collector(collector_name)
@@ -119,6 +120,23 @@ async def _async_collect_and_generate(
     sections_generated = sum(1 for r in sections_results if r.get("success"))
     sections_failed = sum(1 for r in sections_results if not r.get("success"))
 
+    # Index documentation into ChromaDB for RAG
+    logger.info("📚 Indexing generated documentation into ChromaDB...")
+    try:
+        # Initialize agent with vector store
+        agent = DocumentationAgent(vector_store_path="./data/chroma_db")
+
+        # Index all documentation from output directory
+        output_dir = Path("output")
+        if output_dir.exists():
+            await agent.index_documentation(output_dir)
+            logger.info("✅ Documentation indexed successfully into ChromaDB")
+        else:
+            logger.warning("⚠️  Output directory not found, skipping indexing")
+    except Exception as e:
+        logger.error(f"❌ Failed to index documentation: {e}", exc_info=True)
+        # Don't fail the whole task if indexing fails
+
     return {
         "sections_generated": sections_generated,
         "sections_failed": sections_failed,
@@ -155,8 +173,8 @@ async def _get_collector(collector_name: str) -> Any:
     return collectors[collector_name]()
 
 
-@celery_app.task(name="generate_proxmox_docs")
+@celery_app.task(name="generate_proxmox_docs", bind=True)
-def generate_proxmox_docs() -> Dict[str, Any]:
+def generate_proxmox_docs(self) -> Dict[str, Any]:
     """
     Scheduled task to generate Proxmox documentation
 
@@ -165,11 +183,66 @@ def generate_proxmox_docs() -> Dict[str, Any]:
     Returns:
         Task result
     """
-    logger.info("Scheduled Proxmox documentation generation started")
+    import asyncio
+
+    task_id = self.request.id
+    logger.info(f"[{task_id}] Proxmox documentation generation started")
+
+    # Update task state
+    self.update_state(
+        state='PROGRESS',
+        meta={'current': 0, 'total': 6, 'status': 'Starting Proxmox documentation generation...'}
+    )
 
     template_path = "templates/documentation/proxmox.yaml"
 
-    return collect_and_generate_docs(collector_name="proxmox", template_path=template_path)
+    result = {
+        "task_id": task_id,
+        "collector": "proxmox",
+        "template": template_path,
+        "success": False,
+        "started_at": datetime.now().isoformat(),
+        "completed_at": None,
+        "error": None,
+        "sections_generated": 0,
+        "sections_failed": 0,
+    }
+
+    try:
+        # Run async collection and generation directly (don't call another Celery task)
+        loop = asyncio.new_event_loop()
+        asyncio.set_event_loop(loop)
+
+        generation_result = loop.run_until_complete(
+            _async_collect_and_generate("proxmox", template_path)
+        )
+
+        loop.close()
+
+        # Update result
+        result.update(generation_result)
+        result["success"] = True
+        result["completed_at"] = datetime.now().isoformat()
+
+        logger.info(
+            f"[{task_id}] Proxmox documentation generation completed: "
+            f"{result['sections_generated']} sections generated, "
+            f"{result['sections_failed']} failed"
+        )
+
+        return result
+
+    except Exception as e:
+        result["error"] = str(e)
+        result["completed_at"] = datetime.now().isoformat()
+        logger.error(f"[{task_id}] Proxmox documentation generation failed: {e}", exc_info=True)
+
+        self.update_state(
+            state='FAILURE',
+            meta={'error': str(e), 'status': f'Failed: {str(e)}'}
+        )
+
+        raise
 
 
 @celery_app.task(name="generate_all_docs")

templates/documentation/proxmox.yaml

@@ -40,59 +40,107 @@ sections:
 
       Use tables, bullet points, and clear sections. Include actual values from the data.
 
-  - id: "proxmox_vms"
+  - id: "vm"
-    title: "Virtual Machines Inventory"
+    title: "VM: {vm_name}"
-    category: "virtualization"
+    category: "vms"
     priority: 2
-    description: "Complete inventory of QEMU virtual machines"
+    description: "Individual VM documentation"
+    loop_over: "vms"
+    loop_item_name: "vm"
     data_requirements:
-      - "vms"
       - "nodes"
     prompt_template: |
-      Generate detailed documentation for all virtual machines in the Proxmox cluster.
+      Generate detailed technical documentation for this virtual machine.
 
-      **Virtual Machines:**
+      **VM Details:**
-      {vms}
+      {vm}
 
-      **Nodes:**
+      **Available Nodes:**
       {nodes}
 
-      Create documentation that includes:
+      Create comprehensive documentation that includes:
-      1. VM inventory table (VMID, Name, Node, Status, vCPU, RAM, Disk)
-      2. VMs grouped by node
-      3. VMs grouped by status (running/stopped)
-      4. Resource allocation per VM
-      5. Naming conventions and patterns observed
-      6. Recommendations for VM placement and balancing
 
-      Use markdown tables and organize information clearly.
+      ## VM Configuration
+      - VMID and Name
+      - Current Status (running/stopped)
+      - Host Node location
 
-  - id: "proxmox_containers"
+      ## Resource Allocation
-    title: "LXC Containers Inventory"
+      - vCPU cores allocated
-    category: "virtualization"
+      - RAM allocated (in GB)
+      - Disk space and storage location
+      - Network interfaces
+
+      ## Current State
+      - Uptime (if running)
+      - Resource usage (CPU%, RAM%)
+      - IP addresses (if available)
+
+      ## Management
+      - Configuration highlights
+      - Backup status and schedule (if available)
+      - Snapshot information (if available)
+      - High availability configuration (if applicable)
+
+      ## Recommendations
+      - Resource optimization suggestions
+      - Security considerations
+      - Best practices for this VM
+
+      **IMPORTANT**: Document ALL details available in the VM data. Do not skip any information.
+      Use markdown tables, bullet points, and clear sections.
+
+  - id: "container"
+    title: "Container: {container_name}"
+    category: "containers"
     priority: 3
-    description: "Complete inventory of LXC containers"
+    description: "Individual LXC container documentation"
+    loop_over: "containers"
+    loop_item_name: "container"
     data_requirements:
-      - "containers"
       - "nodes"
     prompt_template: |
-      Generate detailed documentation for all LXC containers in the Proxmox cluster.
+      Generate detailed technical documentation for this LXC container.
 
-      **Containers:**
+      **Container Details:**
-      {containers}
+      {container}
 
-      **Nodes:**
+      **Available Nodes:**
       {nodes}
 
-      Create documentation that includes:
+      Create comprehensive documentation that includes:
-      1. Container inventory table (VMID, Name, Node, Status, vCPU, RAM, Disk)
-      2. Containers grouped by node
-      3. Containers grouped by status (running/stopped)
-      4. Resource allocation per container
-      5. Use cases and patterns for containers vs VMs
-      6. Recommendations for container management
 
-      Use markdown tables and clear organization.
+      ## Container Configuration
+      - VMID and Name
+      - Container Type (LXC)
+      - Current Status (running/stopped)
+      - Host Node location
+
+      ## Resource Allocation
+      - vCPU cores allocated
+      - RAM allocated (in GB)
+      - Disk space and storage location
+      - Network interfaces
+
+      ## Current State
+      - Uptime (if running)
+      - Resource usage (CPU%, RAM%)
+      - IP addresses (if available)
+      - Template used (if available)
+
+      ## Management
+      - Configuration highlights
+      - Backup status and schedule (if available)
+      - Snapshot information (if available)
+      - Privileges and security settings
+
+      ## Recommendations
+      - Resource optimization suggestions
+      - Security hardening
+      - Best practices for this container
+
+      **IMPORTANT**: Document ALL details available in the container data. Do not skip any information.
+      Use markdown tables, bullet points, and clear sections.
 
   - id: "proxmox_storage"
     title: "Storage Configuration"
@@ -203,8 +251,8 @@ sections:
 
 # Generation settings
 generation:
-  max_tokens: 4000
+  max_tokens: 2000  # Reduced for small models
-  temperature: 0.7
+  temperature: 0.5  # Lower for more focused responses
   language: "en"  # Default language, can be overridden
 
 # Output configuration