feat(everything): Add document deletion

frontend/src/pages/DocumentsPage.tsx

@@ -29,6 +29,9 @@ import {
   DialogTitle,
   DialogContent,
   DialogActions,
+  Checkbox,
+  Fab,
+  Tooltip,
 } from '@mui/material';
 import Grid from '@mui/material/GridLegacy';
 import {
@@ -49,6 +52,11 @@ import {
   ChevronLeft as ChevronLeftIcon,
   ChevronRight as ChevronRightIcon,
   Edit as EditIcon,
+  Delete as DeleteIcon,
+  CheckBoxOutlineBlank as CheckBoxOutlineBlankIcon,
+  CheckBox as CheckBoxIcon,
+  SelectAll as SelectAllIcon,
+  Close as CloseIcon,
 } from '@mui/icons-material';
 import { documentService } from '../services/api';
 import DocumentThumbnail from '../components/DocumentThumbnail';
@@ -111,6 +119,17 @@ const DocumentsPage: React.FC = () => {
   const [docMenuAnchor, setDocMenuAnchor] = useState<null | HTMLElement>(null);
   const [selectedDoc, setSelectedDoc] = useState<Document | null>(null);
   
+  // Delete confirmation dialog state
+  const [deleteDialogOpen, setDeleteDialogOpen] = useState<boolean>(false);
+  const [documentToDelete, setDocumentToDelete] = useState<Document | null>(null);
+  const [deleteLoading, setDeleteLoading] = useState<boolean>(false);
+
+  // Mass selection state
+  const [selectionMode, setSelectionMode] = useState<boolean>(false);
+  const [selectedDocuments, setSelectedDocuments] = useState<Set<string>>(new Set());
+  const [bulkDeleteDialogOpen, setBulkDeleteDialogOpen] = useState<boolean>(false);
+  const [bulkDeleteLoading, setBulkDeleteLoading] = useState<boolean>(false);
+
   useEffect(() => {
     fetchDocuments();
     fetchLabels();
@@ -281,6 +300,37 @@ const DocumentsPage: React.FC = () => {
     handleSortMenuClose();
   };
 
+  const handleDeleteClick = (doc: Document): void => {
+    setDocumentToDelete(doc);
+    setDeleteDialogOpen(true);
+    handleDocMenuClose();
+  };
+
+  const handleDeleteConfirm = async (): Promise<void> => {
+    if (!documentToDelete) return;
+
+    try {
+      setDeleteLoading(true);
+      await documentService.delete(documentToDelete.id);
+      
+      setDocuments(prev => prev.filter(doc => doc.id !== documentToDelete.id));
+      setPagination(prev => ({ ...prev, total: prev.total - 1 }));
+      
+      setDeleteDialogOpen(false);
+      setDocumentToDelete(null);
+    } catch (error) {
+      console.error('Failed to delete document:', error);
+      setError('Failed to delete document');
+    } finally {
+      setDeleteLoading(false);
+    }
+  };
+
+  const handleDeleteCancel = (): void => {
+    setDeleteDialogOpen(false);
+    setDocumentToDelete(null);
+  };
+
   const handlePageChange = (event: React.ChangeEvent<unknown>, page: number): void => {
     const newOffset = (page - 1) * pagination.limit;
     setPagination(prev => ({ ...prev, offset: newOffset }));
@@ -291,6 +341,61 @@ const DocumentsPage: React.FC = () => {
     setPagination(prev => ({ ...prev, offset: 0 })); // Reset to first page when filtering
   };
 
+  // Mass selection handlers
+  const handleToggleSelectionMode = (): void => {
+    setSelectionMode(!selectionMode);
+    setSelectedDocuments(new Set());
+  };
+
+  const handleDocumentSelect = (documentId: string, isSelected: boolean): void => {
+    const newSelection = new Set(selectedDocuments);
+    if (isSelected) {
+      newSelection.add(documentId);
+    } else {
+      newSelection.delete(documentId);
+    }
+    setSelectedDocuments(newSelection);
+  };
+
+  const handleSelectAll = (): void => {
+    if (selectedDocuments.size === sortedDocuments.length) {
+      setSelectedDocuments(new Set());
+    } else {
+      setSelectedDocuments(new Set(sortedDocuments.map(doc => doc.id)));
+    }
+  };
+
+  const handleBulkDelete = (): void => {
+    if (selectedDocuments.size === 0) return;
+    setBulkDeleteDialogOpen(true);
+  };
+
+  const handleBulkDeleteConfirm = async (): Promise<void> => {
+    if (selectedDocuments.size === 0) return;
+
+    try {
+      setBulkDeleteLoading(true);
+      const documentIds = Array.from(selectedDocuments);
+      await documentService.bulkDelete(documentIds);
+      
+      setDocuments(prev => prev.filter(doc => !selectedDocuments.has(doc.id)));
+      setPagination(prev => ({ ...prev, total: prev.total - selectedDocuments.size }));
+      
+      setSelectedDocuments(new Set());
+      setSelectionMode(false);
+      setBulkDeleteDialogOpen(false);
+    } catch (error) {
+      console.error('Failed to delete documents:', error);
+      setError('Failed to delete selected documents');
+    } finally {
+      setBulkDeleteLoading(false);
+    }
+  };
+
+  const handleBulkDeleteCancel = (): void => {
+    setBulkDeleteDialogOpen(false);
+  };
+
   const getOcrStatusChip = (doc: Document) => {
     if (!doc.ocr_status) return null;
     
@@ -392,6 +497,17 @@ const DocumentsPage: React.FC = () => {
           </ToggleButton>
         </ToggleButtonGroup>
 
+        {/* Selection Mode Toggle */}
+        <Button
+          variant={selectionMode ? "contained" : "outlined"}
+          startIcon={selectionMode ? <CloseIcon /> : <CheckBoxOutlineBlankIcon />}
+          onClick={handleToggleSelectionMode}
+          size="small"
+          color={selectionMode ? "secondary" : "primary"}
+        >
+          {selectionMode ? 'Cancel' : 'Select'}
+        </Button>
+
         {/* OCR Filter */}
         <FormControl size="small" sx={{ minWidth: 120 }}>
           <InputLabel>OCR Status</InputLabel>
@@ -419,6 +535,43 @@ const DocumentsPage: React.FC = () => {
         </Button>
       </Box>
 
+      {/* Selection Toolbar */}
+      {selectionMode && (
+        <Box sx={{ 
+          mb: 2, 
+          p: 2, 
+          bgcolor: 'primary.light',
+          borderRadius: 1,
+          display: 'flex',
+          alignItems: 'center',
+          gap: 2,
+          color: 'primary.contrastText'
+        }}>
+          <Typography variant="body2" sx={{ flexGrow: 1 }}>
+            {selectedDocuments.size} of {sortedDocuments.length} documents selected
+          </Typography>
+          <Button
+            variant="text"
+            startIcon={selectedDocuments.size === sortedDocuments.length ? <CheckBoxIcon /> : <CheckBoxOutlineBlankIcon />}
+            onClick={handleSelectAll}
+            size="small"
+            sx={{ color: 'primary.contrastText' }}
+          >
+            {selectedDocuments.size === sortedDocuments.length ? 'Deselect All' : 'Select All'}
+          </Button>
+          <Button
+            variant="contained"
+            startIcon={<DeleteIcon />}
+            onClick={handleBulkDelete}
+            disabled={selectedDocuments.size === 0}
+            size="small"
+            color="error"
+          >
+            Delete Selected ({selectedDocuments.size})
+          </Button>
+        </Box>
+      )}
+
       {/* Sort Menu */}
       <Menu
         anchorEl={sortMenuAnchor}
@@ -478,6 +631,13 @@ const DocumentsPage: React.FC = () => {
           <ListItemIcon><EditIcon fontSize="small" /></ListItemIcon>
           <ListItemText>Edit Labels</ListItemText>
         </MenuItem>
+        <Divider />
+        <MenuItem onClick={() => { 
+          if (selectedDoc) handleDeleteClick(selectedDoc); 
+        }}>
+          <ListItemIcon><DeleteIcon fontSize="small" color="error" /></ListItemIcon>
+          <ListItemText>Delete</ListItemText>
+        </MenuItem>
       </Menu>
 
       {/* Documents Grid/List */}
@@ -517,13 +677,50 @@ const DocumentsPage: React.FC = () => {
                   flexDirection: viewMode === 'list' ? 'row' : 'column',
                   transition: 'all 0.2s ease-in-out',
                   cursor: 'pointer',
+                  position: 'relative',
                   '&:hover': {
                     transform: 'translateY(-4px)',
                     boxShadow: (theme) => theme.shadows[4],
                   },
+                  ...(selectionMode && selectedDocuments.has(doc.id) && {
+                    boxShadow: (theme) => `0 0 0 2px ${theme.palette.primary.main}`,
+                    bgcolor: 'primary.light',
+                  }),
+                }}
+                onClick={(e) => {
+                  if (selectionMode) {
+                    e.stopPropagation();
+                    handleDocumentSelect(doc.id, !selectedDocuments.has(doc.id));
+                  } else {
+                    navigate(`/documents/${doc.id}`);
+                  }
                 }}
-                onClick={() => navigate(`/documents/${doc.id}`)}
               >
+                {/* Selection checkbox */}
+                {selectionMode && (
+                  <Box
+                    sx={{
+                      position: 'absolute',
+                      top: 8,
+                      right: 8,
+                      zIndex: 1,
+                      bgcolor: 'background.paper',
+                      borderRadius: '50%',
+                      boxShadow: 1,
+                    }}
+                    onClick={(e) => {
+                      e.stopPropagation();
+                      handleDocumentSelect(doc.id, !selectedDocuments.has(doc.id));
+                    }}
+                  >
+                    <Checkbox
+                      checked={selectedDocuments.has(doc.id)}
+                      size="small"
+                      color="primary"
+                    />
+                  </Box>
+                )}
+
                 {viewMode === 'grid' && (
                   <Box
                     sx={{
@@ -628,6 +825,7 @@ const DocumentsPage: React.FC = () => {
                       </Typography>
                     </Box>
                     
+                    {!selectionMode && (
                       <IconButton
                         size="small"
                         onClick={(e) => {
@@ -637,6 +835,7 @@ const DocumentsPage: React.FC = () => {
                       >
                         <MoreIcon />
                       </IconButton>
+                    )}
                   </Box>
                 </CardContent>
                 
@@ -683,6 +882,80 @@ const DocumentsPage: React.FC = () => {
         </DialogActions>
       </Dialog>
 
+      {/* Delete Confirmation Dialog */}
+      <Dialog open={deleteDialogOpen} onClose={handleDeleteCancel} maxWidth="sm">
+        <DialogTitle>Delete Document</DialogTitle>
+        <DialogContent>
+          <Typography>
+            Are you sure you want to delete "{documentToDelete?.original_filename}"?
+          </Typography>
+          <Typography variant="body2" color="text.secondary" sx={{ mt: 1 }}>
+            This action cannot be undone. The document file and all associated data will be permanently removed.
+          </Typography>
+        </DialogContent>
+        <DialogActions>
+          <Button onClick={handleDeleteCancel} disabled={deleteLoading}>
+            Cancel
+          </Button>
+          <Button 
+            onClick={handleDeleteConfirm} 
+            color="error" 
+            variant="contained"
+            disabled={deleteLoading}
+            startIcon={deleteLoading ? <CircularProgress size={16} color="inherit" /> : <DeleteIcon />}
+          >
+            {deleteLoading ? 'Deleting...' : 'Delete'}
+          </Button>
+        </DialogActions>
+      </Dialog>
+
+      {/* Bulk Delete Confirmation Dialog */}
+      <Dialog open={bulkDeleteDialogOpen} onClose={handleBulkDeleteCancel} maxWidth="sm">
+        <DialogTitle>Delete Multiple Documents</DialogTitle>
+        <DialogContent>
+          <Typography gutterBottom>
+            Are you sure you want to delete {selectedDocuments.size} selected document{selectedDocuments.size !== 1 ? 's' : ''}?
+          </Typography>
+          <Typography variant="body2" color="text.secondary" sx={{ mt: 1 }}>
+            This action cannot be undone. All selected documents and their associated data will be permanently removed.
+          </Typography>
+          {selectedDocuments.size > 0 && (
+            <Box sx={{ mt: 2, maxHeight: 200, overflow: 'auto' }}>
+              <Typography variant="subtitle2" gutterBottom>
+                Documents to be deleted:
+              </Typography>
+              {Array.from(selectedDocuments).slice(0, 10).map(docId => {
+                const doc = documents.find(d => d.id === docId);
+                return doc ? (
+                  <Typography key={docId} variant="body2" sx={{ pl: 1 }}>
+                    • {doc.original_filename}
+                  </Typography>
+                ) : null;
+              })}
+              {selectedDocuments.size > 10 && (
+                <Typography variant="body2" sx={{ pl: 1, fontStyle: 'italic' }}>
+                  ... and {selectedDocuments.size - 10} more
+                </Typography>
+              )}
+            </Box>
+          )}
+        </DialogContent>
+        <DialogActions>
+          <Button onClick={handleBulkDeleteCancel} disabled={bulkDeleteLoading}>
+            Cancel
+          </Button>
+          <Button 
+            onClick={handleBulkDeleteConfirm} 
+            color="error" 
+            variant="contained"
+            disabled={bulkDeleteLoading}
+            startIcon={bulkDeleteLoading ? <CircularProgress size={16} color="inherit" /> : <DeleteIcon />}
+          >
+            {bulkDeleteLoading ? 'Deleting...' : `Delete ${selectedDocuments.size} Document${selectedDocuments.size !== 1 ? 's' : ''}`}
+          </Button>
+        </DialogActions>
+      </Dialog>
+
       {/* Results count and pagination */}
       <Box sx={{ mt: 3 }}>
         <Box sx={{ textAlign: 'center', mb: 2 }}>

frontend/src/services/api.ts

@@ -209,6 +209,16 @@ export const documentService = {
   getFacets: () => {
     return api.get<SearchFacetsResponse>('/search/facets')
   },
+
+  delete: (id: string) => {
+    return api.delete(`/documents/${id}`)
+  },
+
+  bulkDelete: (documentIds: string[]) => {
+    return api.delete('/documents', {
+      data: { document_ids: documentIds }
+    })
+  },
 }
 
 export interface OcrStatusResponse {

src/db/documents.rs

@@ -1359,4 +1359,154 @@ impl Database {
 
         Ok(labels_map)
     }
+
+    pub async fn delete_document(&self, document_id: Uuid, user_id: Uuid, user_role: crate::models::UserRole) -> Result<Option<Document>> {
+        let document = if user_role == crate::models::UserRole::Admin {
+            let row = sqlx::query(
+                r#"
+                DELETE FROM documents 
+                WHERE id = $1
+                RETURNING id, filename, original_filename, file_path, file_size, mime_type, content, ocr_text, ocr_confidence, ocr_word_count, ocr_processing_time_ms, ocr_status, ocr_error, ocr_completed_at, tags, created_at, updated_at, user_id, file_hash
+                "#,
+            )
+            .bind(document_id)
+            .fetch_optional(&self.pool)
+            .await?;
+
+            row.map(|r| Document {
+                id: r.get("id"),
+                filename: r.get("filename"),
+                original_filename: r.get("original_filename"),
+                file_path: r.get("file_path"),
+                file_size: r.get("file_size"),
+                mime_type: r.get("mime_type"),
+                content: r.get("content"),
+                ocr_text: r.get("ocr_text"),
+                ocr_confidence: r.get("ocr_confidence"),
+                ocr_word_count: r.get("ocr_word_count"),
+                ocr_processing_time_ms: r.get("ocr_processing_time_ms"),
+                ocr_status: r.get("ocr_status"),
+                ocr_error: r.get("ocr_error"),
+                ocr_completed_at: r.get("ocr_completed_at"),
+                tags: r.get("tags"),
+                created_at: r.get("created_at"),
+                updated_at: r.get("updated_at"),
+                user_id: r.get("user_id"),
+                file_hash: r.get("file_hash"),
+            })
+        } else {
+            let row = sqlx::query(
+                r#"
+                DELETE FROM documents 
+                WHERE id = $1 AND user_id = $2
+                RETURNING id, filename, original_filename, file_path, file_size, mime_type, content, ocr_text, ocr_confidence, ocr_word_count, ocr_processing_time_ms, ocr_status, ocr_error, ocr_completed_at, tags, created_at, updated_at, user_id, file_hash
+                "#,
+            )
+            .bind(document_id)
+            .bind(user_id)
+            .fetch_optional(&self.pool)
+            .await?;
+
+            row.map(|r| Document {
+                id: r.get("id"),
+                filename: r.get("filename"),
+                original_filename: r.get("original_filename"),
+                file_path: r.get("file_path"),
+                file_size: r.get("file_size"),
+                mime_type: r.get("mime_type"),
+                content: r.get("content"),
+                ocr_text: r.get("ocr_text"),
+                ocr_confidence: r.get("ocr_confidence"),
+                ocr_word_count: r.get("ocr_word_count"),
+                ocr_processing_time_ms: r.get("ocr_processing_time_ms"),
+                ocr_status: r.get("ocr_status"),
+                ocr_error: r.get("ocr_error"),
+                ocr_completed_at: r.get("ocr_completed_at"),
+                tags: r.get("tags"),
+                created_at: r.get("created_at"),
+                updated_at: r.get("updated_at"),
+                user_id: r.get("user_id"),
+                file_hash: r.get("file_hash"),
+            })
+        };
+
+        Ok(document)
+    }
+
+    pub async fn bulk_delete_documents(&self, document_ids: &[uuid::Uuid], user_id: uuid::Uuid, user_role: crate::models::UserRole) -> Result<Vec<Document>> {
+        if document_ids.is_empty() {
+            return Ok(Vec::new());
+        }
+
+        let deleted_documents = if user_role == crate::models::UserRole::Admin {
+            let rows = sqlx::query(
+                r#"
+                DELETE FROM documents 
+                WHERE id = ANY($1)
+                RETURNING id, filename, original_filename, file_path, file_size, mime_type, content, ocr_text, ocr_confidence, ocr_word_count, ocr_processing_time_ms, ocr_status, ocr_error, ocr_completed_at, tags, created_at, updated_at, user_id, file_hash
+                "#,
+            )
+            .bind(document_ids)
+            .fetch_all(&self.pool)
+            .await?;
+
+            rows.into_iter().map(|r| Document {
+                id: r.get("id"),
+                filename: r.get("filename"),
+                original_filename: r.get("original_filename"),
+                file_path: r.get("file_path"),
+                file_size: r.get("file_size"),
+                mime_type: r.get("mime_type"),
+                content: r.get("content"),
+                ocr_text: r.get("ocr_text"),
+                ocr_confidence: r.get("ocr_confidence"),
+                ocr_word_count: r.get("ocr_word_count"),
+                ocr_processing_time_ms: r.get("ocr_processing_time_ms"),
+                ocr_status: r.get("ocr_status"),
+                ocr_error: r.get("ocr_error"),
+                ocr_completed_at: r.get("ocr_completed_at"),
+                tags: r.get("tags"),
+                created_at: r.get("created_at"),
+                updated_at: r.get("updated_at"),
+                user_id: r.get("user_id"),
+                file_hash: r.get("file_hash"),
+            }).collect()
+        } else {
+            let rows = sqlx::query(
+                r#"
+                DELETE FROM documents 
+                WHERE id = ANY($1) AND user_id = $2
+                RETURNING id, filename, original_filename, file_path, file_size, mime_type, content, ocr_text, ocr_confidence, ocr_word_count, ocr_processing_time_ms, ocr_status, ocr_error, ocr_completed_at, tags, created_at, updated_at, user_id, file_hash
+                "#,
+            )
+            .bind(document_ids)
+            .bind(user_id)
+            .fetch_all(&self.pool)
+            .await?;
+
+            rows.into_iter().map(|r| Document {
+                id: r.get("id"),
+                filename: r.get("filename"),
+                original_filename: r.get("original_filename"),
+                file_path: r.get("file_path"),
+                file_size: r.get("file_size"),
+                mime_type: r.get("mime_type"),
+                content: r.get("content"),
+                ocr_text: r.get("ocr_text"),
+                ocr_confidence: r.get("ocr_confidence"),
+                ocr_word_count: r.get("ocr_word_count"),
+                ocr_processing_time_ms: r.get("ocr_processing_time_ms"),
+                ocr_status: r.get("ocr_status"),
+                ocr_error: r.get("ocr_error"),
+                ocr_completed_at: r.get("ocr_completed_at"),
+                tags: r.get("tags"),
+                created_at: r.get("created_at"),
+                updated_at: r.get("updated_at"),
+                user_id: r.get("user_id"),
+                file_hash: r.get("file_hash"),
+            }).collect()
+        };
+
+        Ok(deleted_documents)
+    }
 }

src/file_service.rs

@@ -429,4 +429,73 @@ impl FileService {
     pub async fn get_or_generate_thumbnail(&self, _file_path: &str, _filename: &str) -> Result<Vec<u8>> {
         anyhow::bail!("Thumbnail generation requires OCR feature")
     }
+
+    pub async fn delete_document_files(&self, document: &Document) -> Result<()> {
+        let mut deleted_files = Vec::new();
+        let mut errors = Vec::new();
+
+        // Delete main document file
+        let main_file = Path::new(&document.file_path);
+        if main_file.exists() {
+            match fs::remove_file(&main_file).await {
+                Ok(_) => {
+                    deleted_files.push(main_file.to_string_lossy().to_string());
+                    info!("Deleted document file: {}", document.file_path);
+                }
+                Err(e) => {
+                    errors.push(format!("Failed to delete document file {}: {}", document.file_path, e));
+                    warn!("Failed to delete document file {}: {}", document.file_path, e);
+                }
+            }
+        }
+
+        // Delete thumbnail if it exists
+        let thumbnail_filename = format!("{}_thumb.jpg", document.id);
+        let thumbnail_path = self.get_thumbnails_path().join(&thumbnail_filename);
+        if thumbnail_path.exists() {
+            match fs::remove_file(&thumbnail_path).await {
+                Ok(_) => {
+                    deleted_files.push(thumbnail_path.to_string_lossy().to_string());
+                    info!("Deleted thumbnail: {}", thumbnail_path.display());
+                }
+                Err(e) => {
+                    errors.push(format!("Failed to delete thumbnail {}: {}", thumbnail_path.display(), e));
+                    warn!("Failed to delete thumbnail {}: {}", thumbnail_path.display(), e);
+                }
+            }
+        }
+
+        // Delete processed image if it exists
+        let processed_image_filename = format!("{}_processed.png", document.id);
+        let processed_image_path = self.get_processed_images_path().join(&processed_image_filename);
+        if processed_image_path.exists() {
+            match fs::remove_file(&processed_image_path).await {
+                Ok(_) => {
+                    deleted_files.push(processed_image_path.to_string_lossy().to_string());
+                    info!("Deleted processed image: {}", processed_image_path.display());
+                }
+                Err(e) => {
+                    errors.push(format!("Failed to delete processed image {}: {}", processed_image_path.display(), e));
+                    warn!("Failed to delete processed image {}: {}", processed_image_path.display(), e);
+                }
+            }
+        }
+
+        if !errors.is_empty() {
+            // Log all deletion results
+            if !deleted_files.is_empty() {
+                info!("Successfully deleted {} files for document {}", deleted_files.len(), document.id);
+            }
+            error!("Failed to delete some files for document {}: {}", document.id, errors.join("; "));
+            return Err(anyhow::anyhow!("Partial file deletion failure: {}", errors.join("; ")));
+        }
+
+        if deleted_files.is_empty() {
+            warn!("No files found to delete for document {}", document.id);
+        } else {
+            info!("Successfully deleted all {} files for document {}", deleted_files.len(), document.id);
+        }
+
+        Ok(())
+    }
 }

src/routes/documents.rs

@@ -2,7 +2,7 @@ use axum::{
     extract::{Multipart, Path, Query, State},
     http::{StatusCode, header::CONTENT_TYPE},
     response::{Json, Response},
-    routing::{get, post},
+    routing::{get, post, delete},
     Router,
 };
 use serde::Deserialize;
@@ -27,11 +27,18 @@ struct PaginationQuery {
     ocr_status: Option<String>,
 }
 
+#[derive(Deserialize, ToSchema)]
+struct BulkDeleteRequest {
+    document_ids: Vec<uuid::Uuid>,
+}
+
 pub fn router() -> Router<Arc<AppState>> {
     Router::new()
         .route("/", post(upload_document))
         .route("/", get(list_documents))
+        .route("/", delete(bulk_delete_documents))
         .route("/{id}", get(get_document_by_id))
+        .route("/{id}", delete(delete_document))
         .route("/{id}/download", get(download_document))
         .route("/{id}/view", get(view_document))
         .route("/{id}/thumbnail", get(get_document_thumbnail))
@@ -977,3 +984,112 @@ async fn get_user_duplicates(
 
     Ok(Json(response))
 }
+
+#[utoipa::path(
+    delete,
+    path = "/api/documents/{id}",
+    tag = "documents",
+    security(
+        ("bearer_auth" = [])
+    ),
+    params(
+        ("id" = uuid::Uuid, Path, description = "Document ID")
+    ),
+    responses(
+        (status = 200, description = "Document deleted successfully", body = String),
+        (status = 404, description = "Document not found"),
+        (status = 401, description = "Unauthorized")
+    )
+)]
+async fn delete_document(
+    State(state): State<Arc<AppState>>,
+    auth_user: AuthUser,
+    Path(document_id): Path<uuid::Uuid>,
+) -> Result<Json<serde_json::Value>, StatusCode> {
+    let deleted_document = state
+        .db
+        .delete_document(document_id, auth_user.user.id, auth_user.user.role)
+        .await
+        .map_err(|_| StatusCode::INTERNAL_SERVER_ERROR)?
+        .ok_or(StatusCode::NOT_FOUND)?;
+
+    let file_service = FileService::new(state.config.upload_path.clone());
+    
+    if let Err(e) = file_service.delete_document_files(&deleted_document).await {
+        tracing::warn!("Failed to delete some files for document {}: {}", document_id, e);
+    }
+
+    Ok(Json(serde_json::json!({
+        "success": true,
+        "message": "Document deleted successfully",
+        "document_id": document_id,
+        "filename": deleted_document.filename
+    })))
+}
+
+#[utoipa::path(
+    delete,
+    path = "/api/documents",
+    tag = "documents",
+    security(
+        ("bearer_auth" = [])
+    ),
+    request_body(content = BulkDeleteRequest, description = "List of document IDs to delete"),
+    responses(
+        (status = 200, description = "Documents deleted successfully", body = String),
+        (status = 400, description = "Bad request - no document IDs provided"),
+        (status = 401, description = "Unauthorized")
+    )
+)]
+async fn bulk_delete_documents(
+    State(state): State<Arc<AppState>>,
+    auth_user: AuthUser,
+    Json(request): Json<BulkDeleteRequest>,
+) -> Result<Json<serde_json::Value>, StatusCode> {
+    if request.document_ids.is_empty() {
+        return Ok(Json(serde_json::json!({
+            "success": false,
+            "message": "No document IDs provided",
+            "deleted_count": 0
+        })));
+    }
+
+    let deleted_documents = state
+        .db
+        .bulk_delete_documents(&request.document_ids, auth_user.user.id, auth_user.user.role)
+        .await
+        .map_err(|_| StatusCode::INTERNAL_SERVER_ERROR)?;
+
+    let file_service = FileService::new(state.config.upload_path.clone());
+    let mut successful_file_deletions = 0;
+    let mut failed_file_deletions = 0;
+
+    for document in &deleted_documents {
+        match file_service.delete_document_files(document).await {
+            Ok(_) => successful_file_deletions += 1,
+            Err(e) => {
+                failed_file_deletions += 1;
+                tracing::warn!("Failed to delete files for document {}: {}", document.id, e);
+            }
+        }
+    }
+
+    let deleted_count = deleted_documents.len();
+    let requested_count = request.document_ids.len();
+
+    let message = if deleted_count == requested_count {
+        format!("Successfully deleted {} documents", deleted_count)
+    } else {
+        format!("Deleted {} of {} requested documents (some may not exist or belong to other users)", deleted_count, requested_count)
+    };
+
+    Ok(Json(serde_json::json!({
+        "success": true,
+        "message": message,
+        "deleted_count": deleted_count,
+        "requested_count": requested_count,
+        "successful_file_deletions": successful_file_deletions,
+        "failed_file_deletions": failed_file_deletions,
+        "deleted_document_ids": deleted_documents.iter().map(|d| d.id).collect::<Vec<_>>()
+    })))
+}