feat: Add support for generating thumbnails with metadata and enhance file processing capabilities

- Introduced `generateThumbnailWithMetadata` function to generate thumbnails and extract page counts for PDF files.
- Updated `FileContextProvider` to handle processed files with pre-existing thumbnails and metadata.
- Enhanced `useToolOperation` to utilize new thumbnail generation method and manage processed files efficiently.
- Refactored `useToolResources` to include the new thumbnail generation method.
- Updated relevant components to improve logging and error handling during thumbnail generation.

frontend/src/contexts/FileContext.tsx

@@ -46,6 +46,7 @@ import { EnhancedPDFProcessingService } from '../services/enhancedPDFProcessingS
 import { thumbnailGenerationService } from '../services/thumbnailGenerationService';
 import { fileStorage } from '../services/fileStorage';
 import { fileProcessingService } from '../services/fileProcessingService';
+import { generateThumbnailWithMetadata } from '../utils/thumbnailUtils';
 
 // Get service instances
 const enhancedPDFProcessingService = EnhancedPDFProcessingService.getInstance();
@@ -419,7 +420,7 @@ export function FileContextProvider({
 
   // Action implementations
   const addFiles = useCallback(async (files: File[]): Promise<File[]> => {
-    // Three-tier deduplication: UUID (primary key) + quickKey (soft dedupe) + contentHash (hard dedupe)
+    console.log(`📄 addFiles: Adding ${files.length} files with immediate thumbnail generation`);
     const fileRecords: FileRecord[] = [];
     const addedFiles: File[] = [];
     
@@ -443,8 +444,41 @@ export function FileContextProvider({
       // Store File in ref map
       filesRef.current.set(fileId, file);
       
-      // Create record
+      // Generate thumbnail and page count immediately
+      let thumbnail: string | undefined;
+      let pageCount: number = 1;
+      try {
+        console.log(`📄 Generating immediate thumbnail and metadata for ${file.name}`);
+        const result = await generateThumbnailWithMetadata(file);
+        thumbnail = result.thumbnail;
+        pageCount = result.pageCount;
+        console.log(`📄 Generated immediate metadata for ${file.name}: ${pageCount} pages, thumbnail: ${!!thumbnail}`);
+      } catch (error) {
+        console.warn(`📄 Failed to generate immediate metadata for ${file.name}:`, error);
+        // Continue with defaults
+      }
+      
+      // Create record with immediate thumbnail and page metadata
       const record = toFileRecord(file, fileId);
+      if (thumbnail) {
+        record.thumbnailUrl = thumbnail;
+      }
+      
+      // Create initial processedFile metadata with page count
+      if (pageCount > 0) {
+        record.processedFile = {
+          totalPages: pageCount,
+          pages: Array.from({ length: pageCount }, (_, index) => ({
+            pageNumber: index + 1,
+            thumbnail: index === 0 ? thumbnail : undefined, // Only first page gets thumbnail initially
+            rotation: 0,
+            splitBefore: false
+          })),
+          thumbnailUrl: thumbnail,
+          lastProcessed: Date.now()
+        };
+        console.log(`📄 addFiles: Created initial processedFile metadata for ${file.name} with ${pageCount} pages`);
+      }
       
       // Add to deduplication tracking
       existingQuickKeys.add(quickKey);
@@ -452,29 +486,40 @@ export function FileContextProvider({
       fileRecords.push(record);
       addedFiles.push(file);
       
-      // Start centralized file processing (async, non-blocking) - SINGLE CALL
+      // Start background processing for validation only (we already have thumbnail and page count)
       fileProcessingService.processFile(file, fileId).then(result => {
         // Only update if file still exists in context
         if (filesRef.current.has(fileId)) {
           if (result.success && result.metadata) {
-            // Update with processed metadata using dispatch directly
+            // Only log if page count differs from our immediate calculation
+            const initialPageCount = pageCount;
+            if (result.metadata.totalPages !== initialPageCount) {
+              console.log(`📄 Page count validation: ${file.name} initial=${initialPageCount} → final=${result.metadata.totalPages} pages`);
+              // Update with the validated page count, but preserve existing thumbnail
               dispatch({ 
                 type: 'UPDATE_FILE_RECORD', 
                 payload: { 
                   id: fileId, 
                   updates: {
-                  processedFile: result.metadata,
+                    processedFile: {
-                  thumbnailUrl: result.metadata.thumbnailUrl
+                      ...result.metadata,
+                      // Preserve our immediate thumbnail if we have one
+                      thumbnailUrl: thumbnail || result.metadata.thumbnailUrl
+                    },
+                    // Keep existing thumbnailUrl if we have one
+                    thumbnailUrl: thumbnail || result.metadata.thumbnailUrl
                   }
                 }
               });
-            console.log(`✅ File processing complete for ${file.name}: ${result.metadata.totalPages} pages`);
+            } else {
+              console.log(`✅ Page count validation passed for ${file.name}: ${result.metadata.totalPages} pages (immediate generation was correct)`);
+            }
 
-            // Optional: Persist to IndexedDB if enabled (reuse the same result)
+            // Optional: Persist to IndexedDB if enabled
             if (enablePersistence) {
               try {
-                const thumbnail = result.metadata.thumbnailUrl;
+                const finalThumbnail = thumbnail || result.metadata.thumbnailUrl;
-                fileStorage.storeFile(file, fileId, thumbnail).then(() => {
+                fileStorage.storeFile(file, fileId, finalThumbnail).then(() => {
                   console.log('File persisted to IndexedDB:', fileId);
                 }).catch(error => {
                   console.warn('Failed to persist file to IndexedDB:', error);
@@ -484,11 +529,11 @@ export function FileContextProvider({
               }
             }
           } else {
-            console.warn(`❌ File processing failed for ${file.name}:`, result.error);
+            console.warn(`❌ Background file processing failed for ${file.name}:`, result.error);
           }
         }
       }).catch(error => {
-        console.error(`❌ File processing error for ${file.name}:`, error);
+        console.error(`❌ Background file processing error for ${file.name}:`, error);
       });
       
     }
@@ -502,7 +547,118 @@ export function FileContextProvider({
     return addedFiles;
   }, [enablePersistence]); // Remove updateFileRecord dependency
 
+  // NEW: Add processed files with pre-existing thumbnails and metadata (for tool outputs)
+  const addProcessedFiles = useCallback(async (filesWithThumbnails: Array<{ file: File; thumbnail?: string; pageCount?: number }>): Promise<File[]> => {
+    console.log(`📄 addProcessedFiles: Adding ${filesWithThumbnails.length} processed files with pre-existing thumbnails`);
+    const fileRecords: FileRecord[] = [];
+    const addedFiles: File[] = [];
+    
+    // Build quickKey lookup from existing files for deduplication
+    const existingQuickKeys = new Set<string>();
+    Object.values(stateRef.current.files.byId).forEach(record => {
+      existingQuickKeys.add(record.quickKey);
+    });
+    
+    for (const { file, thumbnail, pageCount } of filesWithThumbnails) {
+      const quickKey = createQuickKey(file);
+      
+      // Soft deduplication: Check if file already exists by metadata
+      if (existingQuickKeys.has(quickKey)) {
+        console.log(`📄 Skipping duplicate processed file: ${file.name} (already exists)`);
+        continue; // Skip duplicate file
+      }
+      
+      const fileId = createFileId(); // UUID-based, zero collisions
+      
+      // Store File in ref map
+      filesRef.current.set(fileId, file);
+      
+      // Create record with pre-existing thumbnail and page metadata
+      const record = toFileRecord(file, fileId);
+      if (thumbnail) {
+        record.thumbnailUrl = thumbnail;
+      }
+      
+      // If we have page count, create initial processedFile metadata
+      if (pageCount && pageCount > 0) {
+        record.processedFile = {
+          totalPages: pageCount,
+          pages: Array.from({ length: pageCount }, (_, index) => ({
+            pageNumber: index + 1,
+            thumbnail: index === 0 ? thumbnail : undefined, // Only first page gets thumbnail initially
+            rotation: 0,
+            splitBefore: false
+          })),
+          thumbnailUrl: thumbnail,
+          lastProcessed: Date.now()
+        };
+        console.log(`📄 addProcessedFiles: Created initial processedFile metadata for ${file.name} with ${pageCount} pages`);
+      }
+      
+      // Add to deduplication tracking
+      existingQuickKeys.add(quickKey);
+      
+      fileRecords.push(record);
+      addedFiles.push(file);
+      
+      // Start background processing for page metadata only (thumbnail already provided)
+      fileProcessingService.processFile(file, fileId).then(result => {
+        // Only update if file still exists in context
+        if (filesRef.current.has(fileId)) {
+          if (result.success && result.metadata) {
+            // Update with processed metadata but preserve existing thumbnail
+            dispatch({ 
+              type: 'UPDATE_FILE_RECORD', 
+              payload: { 
+                id: fileId, 
+                updates: {
+                  processedFile: result.metadata,
+                  // Keep existing thumbnail if we already have one, otherwise use processed one
+                  thumbnailUrl: thumbnail || result.metadata.thumbnailUrl
+                }
+              }
+            });
+            // Only log if page count changed (meaning our initial guess was wrong)
+            const initialPageCount = pageCount || 1;
+            if (result.metadata.totalPages !== initialPageCount) {
+              console.log(`📄 Page count updated for ${file.name}: ${initialPageCount} → ${result.metadata.totalPages} pages`);
+            } else {
+              console.log(`✅ Processed file metadata complete for ${file.name}: ${result.metadata.totalPages} pages (thumbnail: ${thumbnail ? 'PRE-EXISTING' : 'GENERATED'})`);
+            }
+
+            // Optional: Persist to IndexedDB if enabled
+            if (enablePersistence) {
+              try {
+                const finalThumbnail = thumbnail || result.metadata.thumbnailUrl;
+                fileStorage.storeFile(file, fileId, finalThumbnail).then(() => {
+                  console.log('Processed file persisted to IndexedDB:', fileId);
+                }).catch(error => {
+                  console.warn('Failed to persist processed file to IndexedDB:', error);
+                });
+              } catch (error) {
+                console.warn('Failed to initiate processed file persistence:', error);
+              }
+            }
+          } else {
+            console.warn(`❌ Processed file background processing failed for ${file.name}:`, result.error);
+          }
+        }
+      }).catch(error => {
+        console.error(`❌ Processed file background processing error for ${file.name}:`, error);
+      });
+    }
+    
+    // Only dispatch if we have new files
+    if (fileRecords.length > 0) {
+      dispatch({ type: 'ADD_FILES', payload: { fileRecords } });
+    }
+
+    console.log(`📄 Added ${fileRecords.length} processed files with pre-existing thumbnails`);
+    return addedFiles;
+  }, [enablePersistence]);
+
   // NEW: Add stored files with preserved IDs to prevent duplicates across sessions
+  // This is the CORRECT way to handle files from IndexedDB storage - no File object mutation
   const addStoredFiles = useCallback(async (filesWithMetadata: Array<{ file: File; originalId: FileId; metadata: FileMetadata }>): Promise<File[]> => {
     const fileRecords: FileRecord[] = [];
     const addedFiles: File[] = [];
@@ -635,6 +791,7 @@ export function FileContextProvider({
   // Memoized actions to prevent re-renders
   const actions = useMemo<FileContextActions>(() => ({
     addFiles,
+    addProcessedFiles,
     addStoredFiles,
     removeFiles,
     updateFileRecord,
@@ -658,7 +815,7 @@ export function FileContextProvider({
     setMode: (mode: ModeType) => dispatch({ type: 'SET_CURRENT_MODE', payload: mode }),
     confirmNavigation,
     cancelNavigation
-  }), [addFiles, addStoredFiles, removeFiles, cleanupAllFiles, setHasUnsavedChanges, confirmNavigation, cancelNavigation]);
+  }), [addFiles, addProcessedFiles, addStoredFiles, removeFiles, cleanupAllFiles, setHasUnsavedChanges, confirmNavigation, cancelNavigation]);
 
   // Split context values to minimize re-renders
   const stateValue = useMemo<FileContextStateValue>(() => ({
@@ -677,6 +834,7 @@ export function FileContextProvider({
     ...state.ui,
     // Action compatibility layer
     addFiles,
+    addProcessedFiles,
     addStoredFiles,
     removeFiles,
     updateFileRecord,
@@ -701,7 +859,7 @@ export function FileContextProvider({
     get activeFiles() { return selectors.getFiles(); }, // Getter to avoid creating new arrays on every render
     // Selectors
     ...selectors
-  }), [state, actions, addFiles, addStoredFiles, removeFiles, updateFileRecord, setHasUnsavedChanges, requestNavigation, confirmNavigation, cancelNavigation, trackBlobUrl, trackPdfDocument, cleanupFile, scheduleCleanup]); // Removed selectors dependency
+  }), [state, actions, addFiles, addProcessedFiles, addStoredFiles, removeFiles, updateFileRecord, setHasUnsavedChanges, requestNavigation, confirmNavigation, cancelNavigation, trackBlobUrl, trackPdfDocument, cleanupFile, scheduleCleanup]); // Removed selectors dependency
 
   // Cleanup on unmount
   useEffect(() => {

frontend/src/hooks/tools/shared/useToolOperation.ts

@@ -121,7 +121,7 @@ export const useToolOperation = <TParams = void>(
   // Composed hooks
   const { state, actions } = useToolState();
   const { processFiles, cancelOperation: cancelApiCalls } = useToolApiCalls<TParams>();
-  const { generateThumbnails, createDownloadInfo, cleanupBlobUrls, extractZipFiles, extractAllZipFiles } = useToolResources();
+  const { generateThumbnails, generateThumbnailsWithMetadata, createDownloadInfo, cleanupBlobUrls, extractZipFiles, extractAllZipFiles } = useToolResources();
 
   const executeOperation = useCallback(async (
     params: TParams,
@@ -167,23 +167,31 @@ export const useToolOperation = <TParams = void>(
         // Use explicit multiFileEndpoint flag to determine processing approach
         if (config.multiFileEndpoint) {
           // Multi-file processing - single API call with all files
+          console.log(`🚀 useToolOperation: Multi-file processing for ${config.operationType} with ${validFiles.length} files`);
           actions.setStatus('Processing files...');
           const formData = (config.buildFormData as (params: TParams, files: File[]) => FormData)(params, validFiles);
           const endpoint = typeof config.endpoint === 'function' ? config.endpoint(params) : config.endpoint;
+          console.log(`🚀 Calling endpoint: ${endpoint}`);
 
           const response = await axios.post(endpoint, formData, { responseType: 'blob' });
+          console.log(`🚀 Received response: ${response.data.size} bytes, type: ${response.data.type}`);
 
           // Multi-file responses are typically ZIP files that need extraction
           if (config.responseHandler) {
+            console.log(`🚀 Using custom responseHandler for ${config.operationType}`);
             // Use custom responseHandler for multi-file (handles ZIP extraction)
             processedFiles = await config.responseHandler(response.data, validFiles);
           } else {
+            console.log(`🚀 Using default ZIP extraction for ${config.operationType}`);
             // Default: assume ZIP response for multi-file endpoints
             processedFiles = await extractZipFiles(response.data);
+            console.log(`🚀 Extracted ${processedFiles.length} files from ZIP`);
 
             if (processedFiles.length === 0) {
+              console.log(`🚀 ZIP extraction failed, trying generic fallback`);
               // Try the generic extraction as fallback
               processedFiles = await extractAllZipFiles(response.data);
+              console.log(`🚀 Generic fallback extracted ${processedFiles.length} files`);
             }
           }
         } else {
@@ -205,21 +213,35 @@ export const useToolOperation = <TParams = void>(
       }
 
       if (processedFiles.length > 0) {
+        console.log(`🚀 useToolOperation: Processing complete. ${processedFiles.length} files ready for thumbnails:`, 
+          processedFiles.map((f, i) => `[${i}]: ${f.name} (${f.type}, ${f.size} bytes)`));
         actions.setFiles(processedFiles);
 
-        // Generate thumbnails and download URL concurrently
+        // Generate thumbnails with metadata and download URL concurrently
         actions.setGeneratingThumbnails(true);
-        const [thumbnails, downloadInfo] = await Promise.all([
+        const [thumbnailResults, downloadInfo] = await Promise.all([
-          generateThumbnails(processedFiles),
+          generateThumbnailsWithMetadata(processedFiles),
           createDownloadInfo(processedFiles, config.operationType)
         ]);
         actions.setGeneratingThumbnails(false);
 
+        // Extract thumbnails for tool state and page counts for context
+        const thumbnails = thumbnailResults.map(r => r.thumbnail || '');
+        const pageCounts = thumbnailResults.map(r => r.pageCount);
+
+        console.log(`⚡ useToolOperation: Generated ${thumbnails.length} thumbnails with page counts for ${config.operationType}:`, 
+          thumbnailResults.map((r, i) => `[${i}]: ${r.thumbnail ? 'PRESENT' : 'MISSING'} (${r.pageCount} pages)`));
         actions.setThumbnails(thumbnails);
         actions.setDownloadInfo(downloadInfo.url, downloadInfo.filename);
 
-        // Add to file context
+        // Add to file context WITH pre-existing thumbnails AND page counts to avoid duplicate processing
-        await fileActions.addFiles(processedFiles);
+        const filesWithMetadata = processedFiles.map((file, index) => ({
+          file,
+          thumbnail: thumbnails[index] || undefined,
+          pageCount: pageCounts[index] || undefined
+        }));
+        console.log(`📄 useToolOperation: Adding ${filesWithMetadata.length} processed files with pre-existing thumbnails and page counts to context`);
+        await fileActions.addProcessedFiles(filesWithMetadata);
 
         markOperationApplied(fileId, operationId);
       }
@@ -233,7 +255,7 @@ export const useToolOperation = <TParams = void>(
       actions.setLoading(false);
       actions.setProgress(null);
     }
-  }, [t, config, actions, processFiles, generateThumbnails, createDownloadInfo, cleanupBlobUrls, extractZipFiles, extractAllZipFiles, fileActions.addFiles]);
+  }, [t, config, actions, processFiles, generateThumbnailsWithMetadata, createDownloadInfo, cleanupBlobUrls, extractZipFiles, extractAllZipFiles, fileActions.addProcessedFiles]);
 
   const cancelOperation = useCallback(() => {
     cancelApiCalls();

frontend/src/hooks/tools/shared/useToolResources.ts

@@ -1,5 +1,5 @@
 import { useState, useCallback, useEffect, useRef } from 'react';
-import { generateThumbnailForFile } from '../../../utils/thumbnailUtils';
+import { generateThumbnailForFile, generateThumbnailWithMetadata, ThumbnailWithMetadata } from '../../../utils/thumbnailUtils';
 import { zipFileService } from '../../../services/zipFileService';
 
 
@@ -43,23 +43,52 @@ export const useToolResources = () => {
   }, []); // No dependencies - use ref to access current URLs
 
   const generateThumbnails = useCallback(async (files: File[]): Promise<string[]> => {
+    console.log(`🖼️ useToolResources.generateThumbnails: Starting for ${files.length} files`);
     const thumbnails: string[] = [];
 
     for (const file of files) {
       try {
+        console.log(`🖼️ Generating thumbnail for: ${file.name} (${file.type}, ${file.size} bytes)`);
         const thumbnail = await generateThumbnailForFile(file);
+        console.log(`🖼️ Generated thumbnail for ${file.name}:`, thumbnail ? 'SUCCESS' : 'FAILED (no thumbnail returned)');
         if (thumbnail) {
           thumbnails.push(thumbnail);
+        } else {
+          console.warn(`🖼️ No thumbnail returned for ${file.name}`);
+          thumbnails.push('');
         }
       } catch (error) {
-        console.warn(`Failed to generate thumbnail for ${file.name}:`, error);
+        console.warn(`🖼️ Failed to generate thumbnail for ${file.name}:`, error);
         thumbnails.push('');
       }
     }
 
+    console.log(`🖼️ useToolResources.generateThumbnails: Complete. Generated ${thumbnails.filter(t => t).length}/${files.length} thumbnails`);
     return thumbnails;
   }, []);
 
+  const generateThumbnailsWithMetadata = useCallback(async (files: File[]): Promise<ThumbnailWithMetadata[]> => {
+    console.log(`🖼️ useToolResources.generateThumbnailsWithMetadata: Starting for ${files.length} files`);
+    const results: ThumbnailWithMetadata[] = [];
+
+    for (const file of files) {
+      try {
+        console.log(`🖼️ Generating thumbnail with metadata for: ${file.name} (${file.type}, ${file.size} bytes)`);
+        const result = await generateThumbnailWithMetadata(file);
+        console.log(`🖼️ Generated thumbnail with metadata for ${file.name}:`, 
+          result.thumbnail ? 'SUCCESS' : 'FAILED (no thumbnail)', 
+          `${result.pageCount} pages`);
+        results.push(result);
+      } catch (error) {
+        console.warn(`🖼️ Failed to generate thumbnail with metadata for ${file.name}:`, error);
+        results.push({ thumbnail: '', pageCount: 1 });
+      }
+    }
+
+    console.log(`🖼️ useToolResources.generateThumbnailsWithMetadata: Complete. Generated ${results.filter(r => r.thumbnail).length}/${files.length} thumbnails with metadata`);
+    return results;
+  }, []);
+
   const extractZipFiles = useCallback(async (zipBlob: Blob): Promise<File[]> => {
     try {
       const zipFile = new File([zipBlob], 'temp.zip', { type: 'application/zip' });
@@ -116,6 +145,7 @@ export const useToolResources = () => {
 
   return {
     generateThumbnails,
+    generateThumbnailsWithMetadata,
     createDownloadInfo,
     extractZipFiles,
     extractAllZipFiles,

frontend/src/hooks/tools/shared/useToolState.ts

@@ -88,6 +88,8 @@ export const useToolState = () => {
   }, []);
 
   const setThumbnails = useCallback((thumbnails: string[]) => {
+    console.log(`🔧 useToolState.setThumbnails: Setting ${thumbnails.length} thumbnails:`, 
+      thumbnails.map((t, i) => `[${i}]: ${t ? 'PRESENT' : 'MISSING'}`));
     dispatch({ type: 'SET_THUMBNAILS', payload: thumbnails });
   }, []);
 

frontend/src/services/fileOperationsService.ts

@@ -47,7 +47,7 @@ export const fileOperationsService = {
     }
     
     try {
-      await fileStorage.init();
+      // fileStorage.init() no longer needed - using centralized IndexedDB manager
       const storedFiles = await fileStorage.getAllFileMetadata();
       
       // Detect if IndexedDB was purged by comparing with current UI state
@@ -189,7 +189,7 @@ export const fileOperationsService = {
     if (currentFiles.length === 0) return false;
     
     try {
-      await fileStorage.init();
+      // fileStorage.init() no longer needed - using centralized IndexedDB manager
       const storedFiles = await fileStorage.getAllFileMetadata();
       return storedFiles.length === 0; // Purge detected if no files in storage but UI shows files
     } catch (error) {

frontend/src/services/fileStorage.ts

@@ -412,7 +412,8 @@ class FileStorageService {
   }
 
   /**
-   * Convert StoredFile back to File object for compatibility
+   * Convert StoredFile back to pure File object without mutations
+   * Returns a clean File object - use FileContext.addStoredFiles() for proper metadata handling
    */
   createFileFromStored(storedFile: StoredFile): File {
     if (!storedFile || !storedFile.data) {
@@ -429,13 +430,27 @@ class FileStorageService {
       lastModified: storedFile.lastModified
     });
 
-    // Add custom properties for compatibility
+    // Returns pure File object - no mutations
-    Object.defineProperty(file, 'id', { value: storedFile.id, writable: false });
+    // Use FileContext.addStoredFiles() to properly associate with metadata
-    Object.defineProperty(file, 'thumbnail', { value: storedFile.thumbnail, writable: false });
-
     return file;
   }
 
+  /**
+   * Convert StoredFile to the format expected by FileContext.addStoredFiles()
+   * This is the recommended way to load stored files into FileContext
+   */
+  createFileWithMetadata(storedFile: StoredFile): { file: File; originalId: string; metadata: { thumbnail?: string } } {
+    const file = this.createFileFromStored(storedFile);
+    
+    return {
+      file,
+      originalId: storedFile.id,
+      metadata: {
+        thumbnail: storedFile.thumbnail
+      }
+    };
+  }
+
   /**
    * Create blob URL for stored file
    */

frontend/src/tools/Split.tsx

@@ -69,13 +69,17 @@ const Split = ({ onPreviewFile, onComplete, onError }: BaseToolProps) => {
   const filesCollapsed = hasFiles;
   const settingsCollapsed = hasResults;
 
-  const previewResults = useMemo(() =>
+  const previewResults = useMemo(() => {
-    splitOperation.files?.map((file, index) => ({
+    const results = splitOperation.files?.map((file, index) => ({
       file,
       thumbnail: splitOperation.thumbnails[index]
-    })) || [],
+    })) || [];
-    [splitOperation.files, splitOperation.thumbnails]
+    
-  );
+    console.log(`🔧 Split tool preview: ${results.length} files, thumbnails:`, 
+      splitOperation.thumbnails.map((t, i) => `[${i}]: ${t ? 'PRESENT' : 'MISSING'}`));
+    
+    return results;
+  }, [splitOperation.files, splitOperation.thumbnails]);
 
   return (
     <ToolStepContainer>

frontend/src/types/fileContext.ts

@@ -191,6 +191,7 @@ export type FileContextAction =
 export interface FileContextActions {
   // File management - lightweight actions only
   addFiles: (files: File[]) => Promise<File[]>;
+  addProcessedFiles: (filesWithThumbnails: Array<{ file: File; thumbnail?: string; pageCount?: number }>) => Promise<File[]>;
   addStoredFiles: (filesWithMetadata: Array<{ file: File; originalId: FileId; metadata: FileMetadata }>) => Promise<File[]>;
   removeFiles: (fileIds: FileId[], deleteFromStorage?: boolean) => void;
   updateFileRecord: (id: FileId, updates: Partial<FileRecord>) => void;

frontend/src/utils/fileUtils.ts

@@ -1,8 +1,34 @@
 import { FileWithUrl } from "../types/file";
 import { StoredFile, fileStorage } from "../services/fileStorage";
 
+/**
+ * @deprecated File objects no longer have mutated ID properties.
+ * The new system maintains pure File objects and tracks IDs separately in FileContext.
+ * Use FileContext selectors to get file IDs instead.
+ */
 export function getFileId(file: File): string | null {
-  return (file as File & { id?: string }).id || null;
+  const legacyId = (file as File & { id?: string }).id;
+  if (legacyId) {
+    console.warn('DEPRECATED: getFileId() found legacy mutated File object. Use FileContext selectors instead.');
+  }
+  return legacyId || null;
+}
+
+/**
+ * Get file ID for a File object using FileContext state (new system)
+ * @param file File object to find ID for
+ * @param fileState Current FileContext state
+ * @returns File ID or null if not found
+ */
+export function getFileIdFromContext(file: File, fileIds: string[], getFile: (id: string) => File | undefined): string | null {
+  // Find the file ID by comparing File objects
+  for (const id of fileIds) {
+    const contextFile = getFile(id);
+    if (contextFile === file) {
+      return id;
+    }
+  }
+  return null;
 }
 
 /**
@@ -81,7 +107,7 @@ export function createEnhancedFileFromStored(storedFile: StoredFile, thumbnail?:
  */
 export async function loadFilesFromIndexedDB(): Promise<FileWithUrl[]> {
   try {
-    await fileStorage.init();
+    // fileStorage.init() no longer needed - using centralized IndexedDB manager
     const storedFiles = await fileStorage.getAllFileMetadata();
 
     if (storedFiles.length === 0) {

frontend/src/utils/thumbnailUtils.ts

@@ -1,5 +1,10 @@
 import { getDocument } from "pdfjs-dist";
 
+export interface ThumbnailWithMetadata {
+  thumbnail: string | undefined;
+  pageCount: number;
+}
+
 /**
  * Calculate thumbnail scale based on file size
  * Smaller files get higher quality, larger files get lower quality
@@ -166,27 +171,36 @@ function formatFileSize(bytes: number): string {
  * Returns base64 data URL or undefined if generation fails
  */
 export async function generateThumbnailForFile(file: File): Promise<string | undefined> {
+  console.log(`🎯 generateThumbnailForFile: Starting for ${file.name} (${file.type}, ${file.size} bytes)`);
+  
   // Skip thumbnail generation for very large files to avoid memory issues
   if (file.size >= 100 * 1024 * 1024) { // 100MB limit
-    console.log('Skipping thumbnail generation for large file:', file.name);
+    console.log('🎯 Skipping thumbnail generation for large file:', file.name);
-    return generatePlaceholderThumbnail(file);
+    const placeholder = generatePlaceholderThumbnail(file);
+    console.log('🎯 Generated placeholder thumbnail for large file:', file.name);
+    return placeholder;
   }
 
   // Handle image files - use original file directly
   if (file.type.startsWith('image/')) {
-    return URL.createObjectURL(file);
+    console.log('🎯 Creating blob URL for image file:', file.name);
+    const url = URL.createObjectURL(file);
+    console.log('🎯 Created image blob URL:', url);
+    return url;
   }
 
   // Handle PDF files
   if (!file.type.startsWith('application/pdf')) {
-    console.log('File is not a PDF or image, generating placeholder:', file.name);
+    console.log('🎯 File is not a PDF or image, generating placeholder:', file.name);
-    return generatePlaceholderThumbnail(file);
+    const placeholder = generatePlaceholderThumbnail(file);
+    console.log('🎯 Generated placeholder thumbnail for non-PDF file:', file.name);
+    return placeholder;
   }
 
   // Calculate quality scale based on file size
-  console.log('Generating thumbnail for', file.name);
+  console.log('🎯 Generating PDF thumbnail for', file.name);
   const scale = calculateScaleFromFileSize(file.size);
-  console.log(`Using scale ${scale} for ${file.name} (${(file.size / 1024 / 1024).toFixed(1)}MB)`);
+  console.log(`🎯 Using scale ${scale} for ${file.name} (${(file.size / 1024 / 1024).toFixed(1)}MB)`);
   try {
     // Only read first 2MB for thumbnail generation to save memory
     const chunkSize = 2 * 1024 * 1024; // 2MB
@@ -215,13 +229,14 @@ export async function generateThumbnailForFile(file: File): Promise<string | und
 
     // Immediately clean up memory after thumbnail generation
     pdf.destroy();
-    console.log('Thumbnail generated and PDF destroyed for', file.name);
+    console.log('🎯 PDF thumbnail successfully generated for', file.name, 'size:', thumbnail.length);
 
     return thumbnail;
   } catch (error) {
+    console.warn('🎯 Error generating PDF thumbnail for', file.name, ':', error);
     if (error instanceof Error) {
       if (error.name === 'InvalidPDFException') {
-        console.warn(`PDF structure issue for ${file.name} - using fallback thumbnail`);
+        console.warn(`🎯 PDF structure issue for ${file.name} - trying fallback with full file`);
         // Return a placeholder or try with full file instead of chunk
         try {
           const fullArrayBuffer = await file.arrayBuffer();
@@ -247,17 +262,132 @@ export async function generateThumbnailForFile(file: File): Promise<string | und
           const thumbnail = canvas.toDataURL();
 
           pdf.destroy();
+          console.log('🎯 Fallback PDF thumbnail generation succeeded for', file.name);
           return thumbnail;
         } catch (fallbackError) {
-          console.warn('Fallback thumbnail generation also failed for', file.name, fallbackError);
+          console.warn('🎯 Fallback thumbnail generation also failed for', file.name, fallbackError);
-          return undefined;
+          console.log('🎯 Using placeholder thumbnail for', file.name);
+          return generatePlaceholderThumbnail(file);
         }
       } else {
-        console.warn('Failed to generate thumbnail for', file.name, error);
+        console.warn('🎯 Non-PDF error generating thumbnail for', file.name, error);
-        return undefined;
+        console.log('🎯 Using placeholder thumbnail for', file.name);
+        return generatePlaceholderThumbnail(file);
       }
     }
-    console.warn('Unknown error generating thumbnail for', file.name, error);
+    console.warn('🎯 Unknown error generating thumbnail for', file.name, error);
-    return undefined;
+    console.log('🎯 Using placeholder thumbnail for', file.name);
+    return generatePlaceholderThumbnail(file);
+  }
+}
+
+/**
+ * Generate thumbnail and extract page count for a PDF file
+ * Returns both thumbnail and metadata in a single pass
+ */
+export async function generateThumbnailWithMetadata(file: File): Promise<ThumbnailWithMetadata> {
+  console.log(`🎯 generateThumbnailWithMetadata: Starting for ${file.name} (${file.type}, ${file.size} bytes)`);
+  
+  // Non-PDF files default to 1 page
+  if (!file.type.startsWith('application/pdf')) {
+    console.log('🎯 File is not a PDF, generating placeholder with pageCount=1:', file.name);
+    const thumbnail = await generateThumbnailForFile(file);
+    return { thumbnail, pageCount: 1 };
+  }
+
+  // Skip thumbnail generation for very large files to avoid memory issues
+  if (file.size >= 100 * 1024 * 1024) { // 100MB limit
+    console.log('🎯 Skipping processing for large PDF file:', file.name);
+    const thumbnail = generatePlaceholderThumbnail(file);
+    return { thumbnail, pageCount: 1 }; // Default to 1 for large files
+  }
+
+  // Calculate quality scale based on file size
+  const scale = calculateScaleFromFileSize(file.size);
+  console.log(`🎯 Using scale ${scale} for ${file.name} (${(file.size / 1024 / 1024).toFixed(1)}MB)`);
+
+  try {
+    // Read file chunk for processing
+    const chunkSize = 2 * 1024 * 1024; // 2MB
+    const chunk = file.slice(0, Math.min(chunkSize, file.size));
+    const arrayBuffer = await chunk.arrayBuffer();
+    
+    const pdf = await getDocument({
+      data: arrayBuffer,
+      disableAutoFetch: true,
+      disableStream: true,
+      verbosity: 0
+    }).promise;
+
+    const pageCount = pdf.numPages;
+    console.log(`🎯 PDF ${file.name} has ${pageCount} pages`);
+
+    // Generate thumbnail for first page
+    const page = await pdf.getPage(1);
+    const viewport = page.getViewport({ scale });
+    const canvas = document.createElement("canvas");
+    canvas.width = viewport.width;
+    canvas.height = viewport.height;
+    const context = canvas.getContext("2d");
+
+    if (!context) {
+      pdf.destroy();
+      throw new Error('Could not get canvas context');
+    }
+
+    await page.render({ canvasContext: context, viewport }).promise;
+    const thumbnail = canvas.toDataURL();
+
+    // Clean up
+    pdf.destroy();
+    
+    console.log('🎯 Successfully generated thumbnail with metadata for', file.name, `${pageCount} pages, thumbnail size:`, thumbnail.length);
+    return { thumbnail, pageCount };
+
+  } catch (error) {
+    console.warn('🎯 Error generating PDF thumbnail with metadata for', file.name, ':', error);
+    
+    // Try fallback with full file if chunk approach failed
+    if (error instanceof Error && error.name === 'InvalidPDFException') {
+      try {
+        console.warn(`🎯 Trying fallback with full file for ${file.name}`);
+        const fullArrayBuffer = await file.arrayBuffer();
+        const pdf = await getDocument({
+          data: fullArrayBuffer,
+          disableAutoFetch: true,
+          disableStream: true,
+          verbosity: 0
+        }).promise;
+
+        const pageCount = pdf.numPages;
+        const page = await pdf.getPage(1);
+        const viewport = page.getViewport({ scale });
+        const canvas = document.createElement("canvas");
+        canvas.width = viewport.width;
+        canvas.height = viewport.height;
+        const context = canvas.getContext("2d");
+
+        if (!context) {
+          pdf.destroy();
+          throw new Error('Could not get canvas context');
+        }
+
+        await page.render({ canvasContext: context, viewport }).promise;
+        const thumbnail = canvas.toDataURL();
+
+        pdf.destroy();
+        
+        console.log('🎯 Fallback successful for', file.name, `${pageCount} pages`);
+        return { thumbnail, pageCount };
+
+      } catch (fallbackError) {
+        console.warn('🎯 Fallback also failed for', file.name, fallbackError);
+      }
+    }
+
+    // Final fallback: placeholder thumbnail with default page count
+    console.log('🎯 Using placeholder thumbnail with default pageCount=1 for', file.name);
+    const thumbnail = generatePlaceholderThumbnail(file);
+    return { thumbnail, pageCount: 1 };
   }
 }