diff --git a/frontend/src/components/fileEditor/FileEditor.tsx b/frontend/src/components/fileEditor/FileEditor.tsx
index f2f76923e..cc76c74bf 100644
--- a/frontend/src/components/fileEditor/FileEditor.tsx
+++ b/frontend/src/components/fileEditor/FileEditor.tsx
@@ -6,6 +6,7 @@ import { Dropzone } from '@mantine/dropzone';
 import { useTranslation } from 'react-i18next';
 import UploadFileIcon from '@mui/icons-material/UploadFile';
 import { useFileSelection, useFileState, useFileManagement } from '../../contexts/FileContext';
+import { FileId } from '../../types/fileContext';
 import { useNavigationActions } from '../../contexts/NavigationContext';
 import { fileStorage } from '../../services/fileStorage';
 import { generateThumbnailForFile } from '../../utils/thumbnailUtils';
@@ -156,26 +157,6 @@ const FileEditor = ({
 
               if (extractionResult.success) {
                 allExtractedFiles.push(...extractionResult.extractedFiles);
-
-                // Record ZIP extraction operation
-                const operationId = `zip-extract-${Date.now()}-${Math.random().toString(36).substr(2, 9)}`;
-                const operation: FileOperation = {
-                id: operationId,
-                type: 'convert',
-                timestamp: Date.now(),
-                fileIds: extractionResult.extractedFiles.map(f => f.name),
-                status: 'pending',
-                metadata: {
-                  originalFileName: file.name,
-                  outputFileNames: extractionResult.extractedFiles.map(f => f.name),
-                  fileSize: file.size,
-                  parameters: {
-                    extractionType: 'zip',
-                    extractedCount: extractionResult.extractedCount,
-                    totalFiles: extractionResult.totalFiles
-                  }
-                }
-              };
               
               if (extractionResult.errors.length > 0) {
                 errors.push(...extractionResult.errors);
@@ -278,7 +259,7 @@ const FileEditor = ({
     }
 
     // Update context (this automatically updates tool selection since they use the same action)
-    setSelectedFiles(newSelection);
+    setSelectedFiles(newSelection.map(id => id as FileId));
   }, [setSelectedFiles, toolMode, setStatus, activeFileRecords]);
 
   const toggleSelectionMode = useCallback(() => {
@@ -306,7 +287,7 @@ const FileEditor = ({
 
     // Handle multi-file selection reordering
     const filesToMove = selectedFileIds.length > 1 
-      ? selectedFileIds.filter(id => currentIds.includes(id))
+      ? selectedFileIds.filter(id => currentIds.includes(id as any))
       : [sourceFileId];
 
     // Create new order
@@ -337,7 +318,7 @@ const FileEditor = ({
     }
 
     // Insert files at the calculated position
-    newOrder.splice(insertIndex, 0, ...filesToMove);
+    newOrder.splice(insertIndex, 0, ...filesToMove.map(id => id as any));
 
     // Update file order
     reorderFiles(newOrder);
@@ -355,31 +336,11 @@ const FileEditor = ({
     const file = record ? selectors.getFile(record.id) : null;
 
     if (record && file) {
-      // Record close operation
-      const fileName = file.name;
-      const contextFileId = record.id;
-      const operationId = `close-${Date.now()}-${Math.random().toString(36).substr(2, 9)}`;
-      const operation: FileOperation = {
-        id: operationId,
-        type: 'remove',
-        timestamp: Date.now(),
-        fileIds: [fileName],
-        status: 'pending',
-        metadata: {
-          originalFileName: fileName,
-          fileSize: record.size,
-          parameters: {
-            action: 'close',
-            reason: 'user_request'
-          }
-        }
-      };
-            
       // Remove file from context but keep in storage (close, don't delete)
-      removeFiles([contextFileId], false);
+      removeFiles([record.id], false);
 
       // Remove from context selections
-      const currentSelected = selectedFileIds.filter(id => id !== contextFileId);
+      const currentSelected = selectedFileIds.filter(id => id !== record.id);
       setSelectedFiles(currentSelected);
     }
   }, [activeFileRecords, selectors, removeFiles, setSelectedFiles, selectedFileIds]);
@@ -388,7 +349,7 @@ const FileEditor = ({
     const record = activeFileRecords.find(r => r.id === fileId);
     if (record) {
       // Set the file as selected in context and switch to viewer for preview
-      setSelectedFiles([fileId]);
+      setSelectedFiles([fileId as FileId]);
       navActions.setMode('viewer');
     }
   }, [activeFileRecords, setSelectedFiles, navActions.setMode]);
@@ -405,7 +366,7 @@ const FileEditor = ({
   }, [activeFileRecords, selectors, onMergeFiles]);
 
   const handleSplitFile = useCallback((fileId: string) => {
-    const file = selectors.getFile(fileId);
+    const file = selectors.getFile(fileId as FileId);
     if (file && onOpenPageEditor) {
       onOpenPageEditor(file);
     }
diff --git a/frontend/src/components/fileEditor/FileEditorThumbnail.tsx b/frontend/src/components/fileEditor/FileEditorThumbnail.tsx
index 2e441a882..bb6ed57f9 100644
--- a/frontend/src/components/fileEditor/FileEditorThumbnail.tsx
+++ b/frontend/src/components/fileEditor/FileEditorThumbnail.tsx
@@ -60,8 +60,8 @@ const FileEditorThumbnail = ({
 
   // Resolve the actual File object for pin/unpin operations
   const actualFile = useMemo(() => {
-    return activeFiles.find((f: File) => f.name === file.name && f.size === file.size);
-  }, [activeFiles, file.name, file.size]);
+    return activeFiles.find(f => f.fileId === file.id);
+  }, [activeFiles, file.id]);
   const isPinned = actualFile ? isFilePinned(actualFile) : false;
 
   const downloadSelectedFile = useCallback(() => {
diff --git a/frontend/src/components/pageEditor/FileThumbnail.tsx b/frontend/src/components/pageEditor/FileThumbnail.tsx
index a0a7d1795..35864f3ef 100644
--- a/frontend/src/components/pageEditor/FileThumbnail.tsx
+++ b/frontend/src/components/pageEditor/FileThumbnail.tsx
@@ -60,8 +60,8 @@ const FileThumbnail = ({
 
   // Resolve the actual File object for pin/unpin operations
   const actualFile = useMemo(() => {
-    return activeFiles.find((f: File) => f.name === file.name && f.size === file.size);
-  }, [activeFiles, file.name, file.size]);
+    return activeFiles.find(f => f.fileId === file.id);
+  }, [activeFiles, file.id]);
   const isPinned = actualFile ? isFilePinned(actualFile) : false;
 
   const downloadSelectedFile = useCallback(() => {
diff --git a/frontend/src/components/pageEditor/hooks/usePageDocument.ts b/frontend/src/components/pageEditor/hooks/usePageDocument.ts
index 5a9d13f9f..48b5e25a9 100644
--- a/frontend/src/components/pageEditor/hooks/usePageDocument.ts
+++ b/frontend/src/components/pageEditor/hooks/usePageDocument.ts
@@ -1,6 +1,7 @@
 import { useMemo } from 'react';
 import { useFileState } from '../../../contexts/FileContext';
 import { PDFDocument, PDFPage } from '../../../types/pageEditor';
+import { FileId } from '../../../types/fileContext';
 
 export interface PageDocumentHook {
   document: PDFDocument | null;
@@ -70,7 +71,7 @@ export function usePageDocument(): PageDocumentHook {
     let totalPageCount = 0;
     
     // Helper function to create pages from a file
-    const createPagesFromFile = (fileId: string, startPageNumber: number): PDFPage[] => {
+    const createPagesFromFile = (fileId: FileId, startPageNumber: number): PDFPage[] => {
       const fileRecord = selectors.getFileRecord(fileId);
       if (!fileRecord) {
         return [];
@@ -111,7 +112,7 @@ export function usePageDocument(): PageDocumentHook {
     // Collect all pages from original files (without renumbering yet)
     const originalFilePages: PDFPage[] = [];
     originalFileIds.forEach(fileId => {
-      const filePages = createPagesFromFile(fileId, 1); // Temporary numbering
+      const filePages = createPagesFromFile(fileId as FileId, 1); // Temporary numbering
       originalFilePages.push(...filePages);
     });
     
@@ -130,7 +131,7 @@ export function usePageDocument(): PageDocumentHook {
       // Collect all pages to insert
       const allNewPages: PDFPage[] = [];
       fileIds.forEach(fileId => {
-        const insertedPages = createPagesFromFile(fileId, 1);
+        const insertedPages = createPagesFromFile(fileId as FileId, 1);
         allNewPages.push(...insertedPages);
       });
       
diff --git a/frontend/src/components/shared/FileGrid.tsx b/frontend/src/components/shared/FileGrid.tsx
index ea0e70818..22d8382e5 100644
--- a/frontend/src/components/shared/FileGrid.tsx
+++ b/frontend/src/components/shared/FileGrid.tsx
@@ -123,10 +123,9 @@ const FileGrid = ({
         style={{ overflowY: "auto", width: "100%" }}
       >
         {displayFiles.map((item, idx) => {
-          // Use record ID if available, otherwise throw error for missing FileRecord
           if (!item.record?.id) {
             console.error('FileGrid: File missing FileRecord with proper ID:', item.file.name);
-            return null; // Skip rendering files without proper IDs
+            return null;
           }
           const fileId = item.record.id;
           const originalIdx = files.findIndex(f => f.record?.id === fileId);
diff --git a/frontend/src/components/tools/convert/ConvertSettings.tsx b/frontend/src/components/tools/convert/ConvertSettings.tsx
index bec6b272f..795e07472 100644
--- a/frontend/src/components/tools/convert/ConvertSettings.tsx
+++ b/frontend/src/components/tools/convert/ConvertSettings.tsx
@@ -22,12 +22,13 @@ import {
   OUTPUT_OPTIONS,
   FIT_OPTIONS
 } from "../../../constants/convertConstants";
+import { FileWithId } from "../../../types/fileContext";
 
 interface ConvertSettingsProps {
   parameters: ConvertParameters;
   onParameterChange: (key: keyof ConvertParameters, value: any) => void;
   getAvailableToExtensions: (fromExtension: string) => Array<{value: string, label: string, group: string}>;
-  selectedFiles: File[];
+  selectedFiles: FileWithId[];
   disabled?: boolean;
 }
 
@@ -128,7 +129,7 @@ const ConvertSettings = ({
   };
 
   const filterFilesByExtension = (extension: string) => {
-    const files = activeFiles.map(fileId => selectors.getFile(fileId)).filter(Boolean) as File[];
+    const files = activeFiles.map(fileId => selectors.getFile(fileId)).filter(Boolean) as FileWithId[];
     return files.filter(file => {
       const fileExtension = detectFileExtension(file.name);
       
@@ -142,21 +143,8 @@ const ConvertSettings = ({
     });
   };
 
-  const updateFileSelection = (files: File[]) => {
-    // Map File objects to their actual IDs in FileContext
-    const fileIds = files.map(file => {
-      // Find the file ID by matching file properties
-      const fileRecord = state.files.ids
-        .map(id => selectors.getFileRecord(id))
-        .find(record => 
-          record && 
-          record.name === file.name && 
-          record.size === file.size && 
-          record.lastModified === file.lastModified
-        );
-      return fileRecord?.id;
-    }).filter((id): id is string => id !== undefined); // Type guard to ensure only strings
-    
+  const updateFileSelection = (files: FileWithId[]) => {
+    const fileIds = files.map(file => file.fileId);
     setSelectedFiles(fileIds);
   };
 
diff --git a/frontend/src/components/tools/convert/ConvertToPdfaSettings.tsx b/frontend/src/components/tools/convert/ConvertToPdfaSettings.tsx
index e1a662bd2..ccad7ce67 100644
--- a/frontend/src/components/tools/convert/ConvertToPdfaSettings.tsx
+++ b/frontend/src/components/tools/convert/ConvertToPdfaSettings.tsx
@@ -3,11 +3,12 @@ import { Stack, Text, Select, Alert } from '@mantine/core';
 import { useTranslation } from 'react-i18next';
 import { ConvertParameters } from '../../../hooks/tools/convert/useConvertParameters';
 import { usePdfSignatureDetection } from '../../../hooks/usePdfSignatureDetection';
+import { FileWithId } from '../../../types/fileContext';
 
 interface ConvertToPdfaSettingsProps {
   parameters: ConvertParameters;
   onParameterChange: (key: keyof ConvertParameters, value: any) => void;
-  selectedFiles: File[];
+  selectedFiles: FileWithId[];
   disabled?: boolean;
 }
 
diff --git a/frontend/src/components/tools/shared/FileStatusIndicator.tsx b/frontend/src/components/tools/shared/FileStatusIndicator.tsx
index 28b8bf428..d8d8b6f51 100644
--- a/frontend/src/components/tools/shared/FileStatusIndicator.tsx
+++ b/frontend/src/components/tools/shared/FileStatusIndicator.tsx
@@ -6,9 +6,10 @@ import UploadIcon from '@mui/icons-material/Upload';
 import { useFilesModalContext } from "../../../contexts/FilesModalContext";
 import { useAllFiles } from "../../../contexts/FileContext";
 import { useFileManager } from "../../../hooks/useFileManager";
+import { FileWithId } from "../../../types/fileContext";
 
 export interface FileStatusIndicatorProps {
-  selectedFiles?: File[];
+  selectedFiles?: FileWithId[];
   placeholder?: string;
 }
 
diff --git a/frontend/src/components/tools/shared/FilesToolStep.tsx b/frontend/src/components/tools/shared/FilesToolStep.tsx
index b062e9c02..11f7d4e02 100644
--- a/frontend/src/components/tools/shared/FilesToolStep.tsx
+++ b/frontend/src/components/tools/shared/FilesToolStep.tsx
@@ -1,9 +1,10 @@
 import React from 'react';
 import { useTranslation } from 'react-i18next';
 import FileStatusIndicator from './FileStatusIndicator';
+import { FileWithId } from '../../../types/fileContext';
 
 export interface FilesToolStepProps {
-  selectedFiles: File[];
+  selectedFiles: FileWithId[];
   isCollapsed?: boolean;
   onCollapsedClick?: () => void;
   placeholder?: string;
diff --git a/frontend/src/components/tools/shared/createToolFlow.tsx b/frontend/src/components/tools/shared/createToolFlow.tsx
index da2503b4e..4662f8eeb 100644
--- a/frontend/src/components/tools/shared/createToolFlow.tsx
+++ b/frontend/src/components/tools/shared/createToolFlow.tsx
@@ -4,9 +4,10 @@ import { createToolSteps, ToolStepProvider } from './ToolStep';
 import OperationButton from './OperationButton';
 import { ToolOperationHook } from '../../../hooks/tools/shared/useToolOperation';
 import { ToolWorkflowTitle, ToolWorkflowTitleProps } from './ToolWorkflowTitle';
+import { FileWithId } from '../../../types/fileContext';
 
 export interface FilesStepConfig {
-  selectedFiles: File[];
+  selectedFiles: FileWithId[];
   isCollapsed?: boolean;
   placeholder?: string;
   onCollapsedClick?: () => void;
diff --git a/frontend/src/components/viewer/Viewer.tsx b/frontend/src/components/viewer/Viewer.tsx
index cdf831c06..f03d16d00 100644
--- a/frontend/src/components/viewer/Viewer.tsx
+++ b/frontend/src/components/viewer/Viewer.tsx
@@ -15,6 +15,7 @@ import { fileStorage } from "../../services/fileStorage";
 import SkeletonLoader from '../shared/SkeletonLoader';
 import { useFileState, useFileActions, useCurrentFile } from "../../contexts/FileContext";
 import { useFileWithUrl } from "../../hooks/useFileWithUrl";
+import { isFileObject } from "../../types/fileContext";
 
 
 // Lazy loading page image component
@@ -200,7 +201,7 @@ const Viewer = ({
   const effectiveFile = React.useMemo(() => {
     if (previewFile) {
       // Validate the preview file
-      if (!(previewFile instanceof File)) {
+      if (!isFileObject(previewFile)) {
         return null;
       }
 
diff --git a/frontend/src/contexts/FileContext.tsx b/frontend/src/contexts/FileContext.tsx
index 9dc893d4d..3f157fe67 100644
--- a/frontend/src/contexts/FileContext.tsx
+++ b/frontend/src/contexts/FileContext.tsx
@@ -89,19 +89,16 @@ function FileContextInner({
       }));
     }
     
-    // Convert to FileWithId objects
     return addedFilesWithIds.map(({ file, id }) => createFileWithId(file, id));
   }, [indexedDB, enablePersistence]);
 
   const addProcessedFiles = useCallback(async (filesWithThumbnails: Array<{ file: File; thumbnail?: string; pageCount?: number }>): Promise<FileWithId[]> => {
     const result = await addFiles('processed', { filesWithThumbnails }, stateRef, filesRef, dispatch, lifecycleManager);
-    // Convert to FileWithId objects  
     return result.map(({ file, id }) => createFileWithId(file, id));
   }, []);
 
   const addStoredFiles = useCallback(async (filesWithMetadata: Array<{ file: File; originalId: FileId; metadata: any }>): Promise<FileWithId[]> => {
     const result = await addFiles('stored', { filesWithMetadata }, stateRef, filesRef, dispatch, lifecycleManager);
-    // Convert to FileWithId objects
     return result.map(({ file, id }) => createFileWithId(file, id));
   }, []);
 
@@ -111,11 +108,9 @@ function FileContextInner({
   // Helper functions for pinned files
   const consumeFilesWrapper = useCallback(async (inputFileIds: FileId[], outputFiles: File[]): Promise<FileWithId[]> => {
     const result = await consumeFiles(inputFileIds, outputFiles, stateRef, filesRef, dispatch);
-    // Convert results to FileWithId objects
     return result.map(({ file, id }) => createFileWithId(file, id));
   }, []);
 
-  // File pinning functions - now use FileWithId directly
   const pinFileWrapper = useCallback((file: FileWithId) => {
     baseActions.pinFile(file.fileId);
   }, [baseActions]);
diff --git a/frontend/src/contexts/file/fileActions.ts b/frontend/src/contexts/file/fileActions.ts
index a623e1901..84fd732f6 100644
--- a/frontend/src/contexts/file/fileActions.ts
+++ b/frontend/src/contexts/file/fileActions.ts
@@ -361,7 +361,6 @@ export async function consumeFiles(
     })
   );
   
-  // Extract records for dispatch
   const outputFileRecords = processedOutputs.map(({ record }) => record);
   
   // Dispatch the consume action
@@ -375,7 +374,6 @@ export async function consumeFiles(
   
   if (DEBUG) console.log(`📄 consumeFiles: Successfully consumed files - removed ${inputFileIds.length} inputs, added ${outputFileRecords.length} outputs`);
   
-  // Return file data for FileWithId conversion
   return processedOutputs.map(({ file, id, thumbnail }) => ({ file, id, thumbnail }));
 }
 
diff --git a/frontend/src/contexts/file/fileHooks.ts b/frontend/src/contexts/file/fileHooks.ts
index 712a96e99..61022c92c 100644
--- a/frontend/src/contexts/file/fileHooks.ts
+++ b/frontend/src/contexts/file/fileHooks.ts
@@ -9,7 +9,7 @@ import {
   FileContextStateValue,
   FileContextActionsValue 
 } from './contexts';
-import { FileId, FileRecord } from '../../types/fileContext';
+import { FileId, FileRecord, FileWithId } from '../../types/fileContext';
 
 /**
  * Hook for accessing file state (will re-render on any state change)
@@ -122,7 +122,7 @@ export function useFileRecord(fileId: FileId): { file?: File; record?: FileRecor
 /**
  * Hook for all files (use sparingly - causes re-renders on file list changes)
  */
-export function useAllFiles(): { files: File[]; records: FileRecord[]; fileIds: FileId[] } {
+export function useAllFiles(): { files: FileWithId[]; records: FileRecord[]; fileIds: FileId[] } {
   const { state, selectors } = useFileState();
   
   return useMemo(() => ({
@@ -135,7 +135,7 @@ export function useAllFiles(): { files: File[]; records: FileRecord[]; fileIds:
 /**
  * Hook for selected files (optimized for selection-based UI)
  */
-export function useSelectedFiles(): { files: File[]; records: FileRecord[]; fileIds: FileId[] } {
+export function useSelectedFiles(): { files: FileWithId[]; records: FileRecord[]; fileIds: FileId[] } {
   const { state, selectors } = useFileState();
   
   return useMemo(() => ({
@@ -164,11 +164,6 @@ export function useFileContext() {
     // File management
     addFiles: actions.addFiles,
     consumeFiles: actions.consumeFiles,
-    recordOperation: (fileId: string, operation: any) => {}, // Operation tracking not implemented
-    markOperationApplied: (fileId: string, operationId: string) => {}, // Operation tracking not implemented  
-    markOperationFailed: (fileId: string, operationId: string, error: string) => {}, // Operation tracking not implemented
-    
-    // File ID lookup removed - use FileWithId.fileId directly for better performance and type safety
     
     // Pinned files
     pinnedFiles: state.pinnedFiles,
diff --git a/frontend/src/contexts/file/lifecycle.ts b/frontend/src/contexts/file/lifecycle.ts
index 99b46495f..b3d6a5cad 100644
--- a/frontend/src/contexts/file/lifecycle.ts
+++ b/frontend/src/contexts/file/lifecycle.ts
@@ -35,10 +35,10 @@ export class FileLifecycleManager {
    */
   cleanupFile = (fileId: string, stateRef?: React.MutableRefObject<any>): void => {
     // Use comprehensive cleanup (same as removeFiles)
-    this.cleanupAllResourcesForFile(fileId, stateRef);
+    this.cleanupAllResourcesForFile(fileId as FileId, stateRef);
     
     // Remove file from state
-    this.dispatch({ type: 'REMOVE_FILES', payload: { fileIds: [fileId] } });
+    this.dispatch({ type: 'REMOVE_FILES', payload: { fileIds: [fileId as FileId] } });
   };
 
   /**
diff --git a/frontend/src/hooks/tools/shared/useToolOperation.ts b/frontend/src/hooks/tools/shared/useToolOperation.ts
index a31d802e4..ae1e2ef26 100644
--- a/frontend/src/hooks/tools/shared/useToolOperation.ts
+++ b/frontend/src/hooks/tools/shared/useToolOperation.ts
@@ -6,7 +6,6 @@ import { useToolState, type ProcessingProgress } from './useToolState';
 import { useToolApiCalls, type ApiCallsConfig } from './useToolApiCalls';
 import { useToolResources } from './useToolResources';
 import { extractErrorMessage } from '../../../utils/toolErrorHandler';
-import { createOperation } from '../../../utils/toolOperationTracker';
 import { FileWithId, extractFiles } from '../../../types/fileContext';
 import { ResponseHandler } from '../../../utils/toolResponseProcessor';
 
@@ -108,7 +107,7 @@ export const useToolOperation = <TParams = void>(
   config: ToolOperationConfig<TParams>
 ): ToolOperationHook<TParams> => {
   const { t } = useTranslation();
-  const { recordOperation, markOperationApplied, markOperationFailed, addFiles, consumeFiles } = useFileContext();
+  const { addFiles, consumeFiles } = useFileContext();
 
   // Composed hooks
   const { state, actions } = useToolState();
@@ -131,9 +130,6 @@ export const useToolOperation = <TParams = void>(
       return;
     }
 
-    // Setup operation tracking with proper FileWithId
-    const { operation, operationId, fileId } = createOperation(config.operationType, params, selectedFiles);
-    recordOperation(fileId, operation);
 
     // Reset state
     actions.setLoading(true);
@@ -144,7 +140,6 @@ export const useToolOperation = <TParams = void>(
     try {
       let processedFiles: File[];
 
-      // Convert FileWithId to regular File objects for API processing
       const validRegularFiles = extractFiles(validFiles);
 
       if (config.customProcessor) {
@@ -214,20 +209,17 @@ export const useToolOperation = <TParams = void>(
         // Replace input files with processed files (consumeFiles handles pinning)
         const inputFileIds = validFiles.map(file => file.fileId);
         await consumeFiles(inputFileIds, processedFiles);
-
-        markOperationApplied(fileId, operationId);
       }
 
     } catch (error: any) {
       const errorMessage = config.getErrorMessage?.(error) || extractErrorMessage(error);
       actions.setError(errorMessage);
       actions.setStatus('');
-      markOperationFailed(fileId, operationId, errorMessage);
     } finally {
       actions.setLoading(false);
       actions.setProgress(null);
     }
-  }, [t, config, actions, recordOperation, markOperationApplied, markOperationFailed, addFiles, consumeFiles, processFiles, generateThumbnails, createDownloadInfo, cleanupBlobUrls, extractZipFiles, extractAllZipFiles]);
+  }, [t, config, actions, addFiles, consumeFiles, processFiles, generateThumbnails, createDownloadInfo, cleanupBlobUrls, extractZipFiles, extractAllZipFiles]);
 
   const cancelOperation = useCallback(() => {
     cancelApiCalls();
diff --git a/frontend/src/hooks/useFileHandler.ts b/frontend/src/hooks/useFileHandler.ts
index b42b4e94c..acfad9674 100644
--- a/frontend/src/hooks/useFileHandler.ts
+++ b/frontend/src/hooks/useFileHandler.ts
@@ -1,6 +1,7 @@
 import { useCallback } from 'react';
 import { useFileState, useFileActions } from '../contexts/FileContext';
 import { FileMetadata } from '../types/file';
+import { FileId } from '../types/fileContext';
 
 export const useFileHandler = () => {
   const { state } = useFileState(); // Still needed for addStoredFiles
@@ -20,11 +21,15 @@ export const useFileHandler = () => {
   const addStoredFiles = useCallback(async (filesWithMetadata: Array<{ file: File; originalId: string; metadata: FileMetadata }>) => {
     // Filter out files that already exist with the same ID (exact match)
     const newFiles = filesWithMetadata.filter(({ originalId }) => {
-      return state.files.byId[originalId] === undefined;
+      return state.files.byId[originalId as FileId] === undefined;
     });
     
     if (newFiles.length > 0) {
-      await actions.addStoredFiles(newFiles);
+      await actions.addStoredFiles(newFiles.map(({file, originalId, metadata}) => ({
+        file, 
+        originalId: originalId as FileId, 
+        metadata
+      })));
     }
     
     console.log(`📁 Added ${newFiles.length} stored files (${filesWithMetadata.length - newFiles.length} skipped as duplicates)`);
diff --git a/frontend/src/hooks/useFileManager.ts b/frontend/src/hooks/useFileManager.ts
index 59e8c1cdb..05816efd3 100644
--- a/frontend/src/hooks/useFileManager.ts
+++ b/frontend/src/hooks/useFileManager.ts
@@ -2,6 +2,7 @@ import { useState, useCallback } from 'react';
 import { useIndexedDB } from '../contexts/IndexedDBContext';
 import { FileMetadata } from '../types/file';
 import { generateThumbnailForFile } from '../utils/thumbnailUtils';
+import { FileId } from '../types/fileContext';
 
 export const useFileManager = () => {
   const [loading, setLoading] = useState(false);
@@ -46,7 +47,7 @@ export const useFileManager = () => {
     
     // Regular file loading
     if (fileMetadata.id) {
-      const file = await indexedDB.loadFile(fileMetadata.id);
+      const file = await indexedDB.loadFile(fileMetadata.id as FileId);
       if (file) {
         return file;
       }
@@ -86,7 +87,7 @@ export const useFileManager = () => {
       throw new Error('IndexedDB context not available');
     }
     try {
-      await indexedDB.deleteFile(file.id);
+      await indexedDB.deleteFile(file.id as FileId);
       setFiles(files.filter((_, i) => i !== index));
     } catch (error) {
       console.error('Failed to remove file:', error);
@@ -100,7 +101,7 @@ export const useFileManager = () => {
     }
     try {
       // Store file with provided UUID from FileContext (thumbnail generated internally)
-      const metadata = await indexedDB.saveFile(file, fileId);
+      const metadata = await indexedDB.saveFile(file, fileId as FileId);
 
       // Convert file to ArrayBuffer for StoredFile interface compatibility
       const arrayBuffer = await file.arrayBuffer();
@@ -176,7 +177,7 @@ export const useFileManager = () => {
     try {
       // Update access time - this will be handled by the cache in IndexedDBContext
       // when the file is loaded, so we can just load it briefly to "touch" it
-      await indexedDB.loadFile(id);
+      await indexedDB.loadFile(id as FileId);
     } catch (error) {
       console.error('Failed to touch file:', error);
     }
diff --git a/frontend/src/hooks/useFileWithUrl.ts b/frontend/src/hooks/useFileWithUrl.ts
index fd2f2d604..84c06baa2 100644
--- a/frontend/src/hooks/useFileWithUrl.ts
+++ b/frontend/src/hooks/useFileWithUrl.ts
@@ -1,4 +1,5 @@
 import { useMemo } from 'react';
+import { isFileObject } from '../types/fileContext';
 
 /**
  * Hook to convert a File object to { file: File; url: string } format
@@ -8,8 +9,8 @@ export function useFileWithUrl(file: File | Blob | null): { file: File | Blob; u
   return useMemo(() => {
     if (!file) return null;
 
-    // Validate that file is a proper File or Blob object
-    if (!(file instanceof File) && !(file instanceof Blob)) {
+    // Validate that file is a proper File, FileWithId, or Blob object
+    if (!isFileObject(file) && !(file instanceof Blob)) {
       console.warn('useFileWithUrl: Expected File or Blob, got:', file);
       return null;
     }
diff --git a/frontend/src/hooks/useIndexedDBThumbnail.ts b/frontend/src/hooks/useIndexedDBThumbnail.ts
index 4f0d77c0e..a6251db3c 100644
--- a/frontend/src/hooks/useIndexedDBThumbnail.ts
+++ b/frontend/src/hooks/useIndexedDBThumbnail.ts
@@ -2,6 +2,7 @@ import { useState, useEffect } from "react";
 import { FileMetadata } from "../types/file";
 import { useIndexedDB } from "../contexts/IndexedDBContext";
 import { generateThumbnailForFile } from "../utils/thumbnailUtils";
+import { FileId } from "../types/fileContext";
 
 /**
  * Calculate optimal scale for thumbnail generation
@@ -53,7 +54,7 @@ export function useIndexedDBThumbnail(file: FileMetadata | undefined | null): {
 
           // Try to load file from IndexedDB using new context
           if (file.id && indexedDB) {
-            const loadedFile = await indexedDB.loadFile(file.id);
+            const loadedFile = await indexedDB.loadFile(file.id as FileId);
             if (!loadedFile) {
               throw new Error('File not found in IndexedDB');
             }
@@ -70,7 +71,7 @@ export function useIndexedDBThumbnail(file: FileMetadata | undefined | null): {
             // Save thumbnail to IndexedDB for persistence
             if (file.id && indexedDB && thumbnail) {
               try {
-                await indexedDB.updateThumbnail(file.id, thumbnail);
+                await indexedDB.updateThumbnail(file.id as FileId, thumbnail);
               } catch (error) {
                 console.warn('Failed to save thumbnail to IndexedDB:', error);
               }
diff --git a/frontend/src/hooks/usePdfSignatureDetection.ts b/frontend/src/hooks/usePdfSignatureDetection.ts
index 17f90f2d9..84075f972 100644
--- a/frontend/src/hooks/usePdfSignatureDetection.ts
+++ b/frontend/src/hooks/usePdfSignatureDetection.ts
@@ -1,13 +1,14 @@
 import { useState, useEffect } from 'react';
 import * as pdfjsLib from 'pdfjs-dist';
 import { pdfWorkerManager } from '../services/pdfWorkerManager';
+import { FileWithId } from '../types/fileContext';
 
 export interface PdfSignatureDetectionResult {
   hasDigitalSignatures: boolean;
   isChecking: boolean;
 }
 
-export const usePdfSignatureDetection = (files: File[]): PdfSignatureDetectionResult => {
+export const usePdfSignatureDetection = (files: FileWithId[]): PdfSignatureDetectionResult => {
   const [hasDigitalSignatures, setHasDigitalSignatures] = useState(false);
   const [isChecking, setIsChecking] = useState(false);
 
diff --git a/frontend/src/hooks/useThumbnailGeneration.ts b/frontend/src/hooks/useThumbnailGeneration.ts
index bbb599c3b..6b0b6856f 100644
--- a/frontend/src/hooks/useThumbnailGeneration.ts
+++ b/frontend/src/hooks/useThumbnailGeneration.ts
@@ -71,7 +71,6 @@ async function processRequestQueue() {
           
           console.log(`📸 Batch generating ${requests.length} thumbnails for pages: ${pageNumbers.slice(0, 5).join(', ')}${pageNumbers.length > 5 ? '...' : ''}`);
           
-          // Use quickKey for PDF document caching (same metadata, consistent format)
           const fileId = createQuickKey(file);
           
           const results = await thumbnailGenerationService.generateThumbnails(
diff --git a/frontend/src/tests/convert/ConvertIntegration.test.tsx b/frontend/src/tests/convert/ConvertIntegration.test.tsx
index 1ce180b9f..baa7f1216 100644
--- a/frontend/src/tests/convert/ConvertIntegration.test.tsx
+++ b/frontend/src/tests/convert/ConvertIntegration.test.tsx
@@ -18,6 +18,8 @@ import { FileContextProvider } from '../../contexts/FileContext';
 import { I18nextProvider } from 'react-i18next';
 import i18n from '../../i18n/config';
 import axios from 'axios';
+import { createTestFileWithId } from '../utils/testFileHelpers';
+import { FileWithId } from '../../types/fileContext';
 
 // Mock axios
 vi.mock('axios');
@@ -55,9 +57,9 @@ const createTestFile = (name: string, content: string, type: string): File => {
   return new File([content], name, { type });
 };
 
-const createPDFFile = (): File => {
+const createPDFFile = (): FileWithId => {
   const pdfContent = '%PDF-1.4\n1 0 obj\n<<\n/Type /Catalog\n/Pages 2 0 R\n>>\nendobj\ntrailer\n<<\n/Size 2\n/Root 1 0 R\n>>\nstartxref\n0\n%%EOF';
-  return createTestFile('test.pdf', pdfContent, 'application/pdf');
+  return createTestFileWithId('test.pdf', pdfContent, 'application/pdf');
 };
 
 // Test wrapper component
@@ -162,7 +164,7 @@ describe('Convert Tool Integration Tests', () => {
         wrapper: TestWrapper
       });
 
-      const testFile = createTestFile('invalid.txt', 'not a pdf', 'text/plain');
+      const testFile = createTestFileWithId('invalid.txt', 'not a pdf', 'text/plain');
       const parameters: ConvertParameters = {
         fromExtension: 'pdf',
         toExtension: 'png',
@@ -426,7 +428,7 @@ describe('Convert Tool Integration Tests', () => {
       });
       const files = [
         createPDFFile(),
-        createTestFile('test2.pdf', '%PDF-1.4...', 'application/pdf')
+        createTestFileWithId('test2.pdf', '%PDF-1.4...', 'application/pdf')
       ]
       const parameters: ConvertParameters = {
         fromExtension: 'pdf',
@@ -527,7 +529,7 @@ describe('Convert Tool Integration Tests', () => {
         wrapper: TestWrapper
       });
 
-      const corruptedFile = createTestFile('corrupted.pdf', 'not-a-pdf', 'application/pdf');
+      const corruptedFile = createTestFileWithId('corrupted.pdf', 'not-a-pdf', 'application/pdf');
       const parameters: ConvertParameters = {
         fromExtension: 'pdf',
         toExtension: 'png',
diff --git a/frontend/src/tests/convert/ConvertSmartDetectionIntegration.test.tsx b/frontend/src/tests/convert/ConvertSmartDetectionIntegration.test.tsx
index 4038df63b..7c160f197 100644
--- a/frontend/src/tests/convert/ConvertSmartDetectionIntegration.test.tsx
+++ b/frontend/src/tests/convert/ConvertSmartDetectionIntegration.test.tsx
@@ -14,6 +14,8 @@ import i18n from '../../i18n/config';
 import axios from 'axios';
 import { detectFileExtension } from '../../utils/fileUtils';
 import { FIT_OPTIONS } from '../../constants/convertConstants';
+import { createTestFileWithId, createTestFilesWithId } from '../utils/testFileHelpers';
+import { FileWithId } from '../../types/fileContext';
 
 // Mock axios
 vi.mock('axios');
@@ -81,7 +83,7 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
       });
 
       // Create mock DOCX file
-      const docxFile = new File(['docx content'], 'document.docx', { type: 'application/vnd.openxmlformats-officedocument.wordprocessingml.document' });
+      const docxFile = createTestFileWithId('document.docx', 'docx content', 'application/vnd.openxmlformats-officedocument.wordprocessingml.document');
 
       // Test auto-detection
       act(() => {
@@ -117,7 +119,7 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
       });
 
       // Create mock unknown file
-      const unknownFile = new File(['unknown content'], 'document.xyz', { type: 'application/octet-stream' });
+      const unknownFile = createTestFileWithId('document.xyz', 'unknown content', 'application/octet-stream');
 
       // Test auto-detection
       act(() => {
@@ -156,11 +158,11 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
       });
 
       // Create mock image files
-      const imageFiles = [
-        new File(['jpg content'], 'photo1.jpg', { type: 'image/jpeg' }),
-        new File(['png content'], 'photo2.png', { type: 'image/png' }),
-        new File(['gif content'], 'photo3.gif', { type: 'image/gif' })
-      ];
+      const imageFiles = createTestFilesWithId([
+        { name: 'photo1.jpg', content: 'jpg content', type: 'image/jpeg' },
+        { name: 'photo2.png', content: 'png content', type: 'image/png' },
+        { name: 'photo3.gif', content: 'gif content', type: 'image/gif' }
+      ]);
 
       // Test smart detection for all images
       act(() => {
@@ -202,11 +204,11 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
       });
 
       // Create mixed file types
-      const mixedFiles = [
-        new File(['pdf content'], 'document.pdf', { type: 'application/pdf' }),
-        new File(['docx content'], 'spreadsheet.xlsx', { type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet' }),
-        new File(['pptx content'], 'presentation.pptx', { type: 'application/vnd.openxmlformats-officedocument.presentationml.presentation' })
-      ];
+      const mixedFiles = createTestFilesWithId([
+        { name: 'document.pdf', content: 'pdf content', type: 'application/pdf' },
+        { name: 'spreadsheet.xlsx', content: 'docx content', type: 'application/vnd.openxmlformats-officedocument.spreadsheetml.sheet' },
+        { name: 'presentation.pptx', content: 'pptx content', type: 'application/vnd.openxmlformats-officedocument.presentationml.presentation' }
+      ]);
 
       // Test smart detection for mixed types
       act(() => {
@@ -243,10 +245,10 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
       });
 
       // Create mock web files
-      const webFiles = [
-        new File(['<html>content</html>'], 'page1.html', { type: 'text/html' }),
-        new File(['zip content'], 'site.zip', { type: 'application/zip' })
-      ];
+      const webFiles = createTestFilesWithId([
+        { name: 'page1.html', content: '<html>content</html>', type: 'text/html' },
+        { name: 'site.zip', content: 'zip content', type: 'application/zip' }
+      ]);
 
       // Test smart detection for web files
       act(() => {
@@ -288,7 +290,7 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
         wrapper: TestWrapper
       });
 
-      const htmlFile = new File(['<html>content</html>'], 'page.html', { type: 'text/html' });
+      const htmlFile = createTestFileWithId('page.html', '<html>content</html>', 'text/html');
 
       // Set up HTML conversion parameters
       act(() => {
@@ -318,7 +320,7 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
         wrapper: TestWrapper
       });
 
-      const emlFile = new File(['email content'], 'email.eml', { type: 'message/rfc822' });
+      const emlFile = createTestFileWithId('email.eml', 'email content', 'message/rfc822');
 
       // Set up email conversion parameters
       act(() => {
@@ -355,7 +357,7 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
         wrapper: TestWrapper
       });
 
-      const pdfFile = new File(['pdf content'], 'document.pdf', { type: 'application/pdf' });
+      const pdfFile = createTestFileWithId('document.pdf', 'pdf content', 'application/pdf');
 
       // Set up PDF/A conversion parameters
       act(() => {
@@ -392,10 +394,10 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
         wrapper: TestWrapper
       });
 
-      const imageFiles = [
-        new File(['jpg1'], 'photo1.jpg', { type: 'image/jpeg' }),
-        new File(['jpg2'], 'photo2.jpg', { type: 'image/jpeg' })
-      ];
+      const imageFiles = createTestFilesWithId([
+        { name: 'photo1.jpg', content: 'jpg1', type: 'image/jpeg' },
+        { name: 'photo2.jpg', content: 'jpg2', type: 'image/jpeg' }
+      ]);
 
       // Set up image conversion parameters
       act(() => {
@@ -432,10 +434,10 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
         wrapper: TestWrapper
       });
 
-      const imageFiles = [
-        new File(['jpg1'], 'photo1.jpg', { type: 'image/jpeg' }),
-        new File(['jpg2'], 'photo2.jpg', { type: 'image/jpeg' })
-      ];
+      const imageFiles = createTestFilesWithId([
+        { name: 'photo1.jpg', content: 'jpg1', type: 'image/jpeg' },
+        { name: 'photo2.jpg', content: 'jpg2', type: 'image/jpeg' }
+      ]);
 
       // Set up for separate processing
       act(() => {
@@ -477,10 +479,10 @@ describe('Convert Tool - Smart Detection Integration Tests', () => {
         })
         .mockRejectedValueOnce(new Error('File 2 failed'));
 
-      const mixedFiles = [
-        new File(['file1'], 'doc1.txt', { type: 'text/plain' }),
-        new File(['file2'], 'doc2.xyz', { type: 'application/octet-stream' })
-      ];
+      const mixedFiles = createTestFilesWithId([
+        { name: 'doc1.txt', content: 'file1', type: 'text/plain' },
+        { name: 'doc2.xyz', content: 'file2', type: 'application/octet-stream' }
+      ]);
 
       // Set up for separate processing (mixed smart detection)
       act(() => {
diff --git a/frontend/src/tests/utils/testFileHelpers.ts b/frontend/src/tests/utils/testFileHelpers.ts
new file mode 100644
index 000000000..be8cd9774
--- /dev/null
+++ b/frontend/src/tests/utils/testFileHelpers.ts
@@ -0,0 +1,28 @@
+/**
+ * Test utilities for creating FileWithId objects in tests
+ */
+
+import { FileWithId, createFileWithId } from '../../types/fileContext';
+
+/**
+ * Create a FileWithId object for testing purposes
+ */
+export function createTestFileWithId(
+  name: string,
+  content: string = 'test content',
+  type: string = 'application/pdf'
+): FileWithId {
+  const file = new File([content], name, { type });
+  return createFileWithId(file);
+}
+
+/**
+ * Create multiple FileWithId objects for testing
+ */
+export function createTestFilesWithId(
+  files: Array<{ name: string; content?: string; type?: string }>
+): FileWithId[] {
+  return files.map(({ name, content = 'test content', type = 'application/pdf' }) =>
+    createTestFileWithId(name, content, type)
+  );
+}
\ No newline at end of file
diff --git a/frontend/src/types/fileContext.ts b/frontend/src/types/fileContext.ts
index aa12cbad7..103fae088 100644
--- a/frontend/src/types/fileContext.ts
+++ b/frontend/src/types/fileContext.ts
@@ -69,14 +69,14 @@ export interface FileContextNormalizedFiles {
 export function createFileId(): FileId {
   // Use crypto.randomUUID for authoritative primary key
   if (typeof window !== 'undefined' && window.crypto?.randomUUID) {
-    return window.crypto.randomUUID();
+    return window.crypto.randomUUID() as FileId;
   }
   // Fallback for environments without randomUUID
   return 'xxxxxxxx-xxxx-4xxx-yxxx-xxxxxxxxxxxx'.replace(/[xy]/g, function(c) {
     const r = Math.random() * 16 | 0;
     const v = c == 'x' ? r : (r & 0x3 | 0x8);
     return v.toString(16);
-  });
+  }) as FileId;
 }
 
 // Generate quick deduplication key from file metadata
@@ -102,22 +102,26 @@ export function createFileWithId(file: File, id?: FileId): FileWithId {
   const fileId = id || createFileId();
   const quickKey = createQuickKey(file);
   
-  // Create new File-like object with embedded fileId and quickKey
-  const fileWithId = Object.create(file);
-  Object.defineProperty(fileWithId, 'fileId', {
+  const newFile = new File([file], file.name, {
+    type: file.type,
+    lastModified: file.lastModified
+  });
+  
+  Object.defineProperty(newFile, 'fileId', {
     value: fileId,
     writable: false,
     enumerable: true,
     configurable: false
   });
-  Object.defineProperty(fileWithId, 'quickKey', {
+  
+  Object.defineProperty(newFile, 'quickKey', {
     value: quickKey,
     writable: false,
     enumerable: true,
     configurable: false
   });
   
-  return fileWithId as FileWithId;
+  return newFile as FileWithId;
 }
 
 // Wrap array of Files with FileIds
@@ -132,19 +136,22 @@ export function extractFileIds(files: FileWithId[]): FileId[] {
   return files.map(file => file.fileId);
 }
 
-// Extract regular File objects from FileWithId array
 export function extractFiles(files: FileWithId[]): File[] {
-  return files.map(file => {
-    // Create clean File object without the fileId property
-    return new File([file], file.name, {
-      type: file.type,
-      lastModified: file.lastModified
-    });
-  });
+  return files as File[];
 }
 
 // Type guards and validation functions
 
+// Check if an object is a File or FileWithId (replaces instanceof File checks)
+export function isFileObject(obj: any): obj is File | FileWithId {
+  return obj && 
+         typeof obj.name === 'string' &&
+         typeof obj.size === 'number' &&
+         typeof obj.type === 'string' &&
+         typeof obj.lastModified === 'number' &&
+         typeof obj.arrayBuffer === 'function';
+}
+
 // Validate that a string is a proper FileId (has UUID format)
 export function isValidFileId(id: string): id is FileId {
   // Check UUID v4 format: 8-4-4-4-12 hex digits
@@ -257,7 +264,7 @@ export interface FileOperation {
   id: string;
   type: OperationType;
   timestamp: number;
-  fileIds: string[];
+  fileIds: FileId[];
   status: 'pending' | 'applied' | 'failed';
   data?: any;
   metadata?: {
@@ -271,7 +278,7 @@ export interface FileOperation {
 }
 
 export interface FileOperationHistory {
-  fileId: string;
+  fileId: FileId;
   fileName: string;
   operations: (FileOperation | PageOperation)[];
   createdAt: number;
@@ -286,7 +293,7 @@ export interface ViewerConfig {
 }
 
 export interface FileEditHistory {
-  fileId: string;
+  fileId: FileId;
   pageOperations: PageOperation[];
   lastModified: number;
 }
@@ -369,26 +376,19 @@ export interface FileContextActions {
   
   // Resource management
   trackBlobUrl: (url: string) => void;
-  scheduleCleanup: (fileId: string, delay?: number) => void;
-  cleanupFile: (fileId: string) => void;
+  scheduleCleanup: (fileId: FileId, delay?: number) => void;
+  cleanupFile: (fileId: FileId) => void;
 }
 
 // File selectors (separate from actions to avoid re-renders)
 export interface FileContextSelectors {
-  // File access - now returns FileWithId for safer type checking
   getFile: (id: FileId) => FileWithId | undefined;
   getFiles: (ids?: FileId[]) => FileWithId[];
-  
-  // Record access - uses normalized state
   getFileRecord: (id: FileId) => FileRecord | undefined;
   getFileRecords: (ids?: FileId[]) => FileRecord[];
-  
-  // Derived selectors - now return FileWithId
   getAllFileIds: () => FileId[];
   getSelectedFiles: () => FileWithId[];
   getSelectedFileRecords: () => FileRecord[];
-  
-  // Pinned files selectors - now return FileWithId
   getPinnedFileIds: () => FileId[];
   getPinnedFiles: () => FileWithId[];
   getPinnedFileRecords: () => FileRecord[];
diff --git a/frontend/src/types/fileIdSafety.d.ts b/frontend/src/types/fileIdSafety.d.ts
index cbe41a56c..897dcf6c9 100644
--- a/frontend/src/types/fileIdSafety.d.ts
+++ b/frontend/src/types/fileIdSafety.d.ts
@@ -2,7 +2,7 @@
  * Type safety declarations to prevent file.name/UUID confusion
  */
 
-import { FileId, FileWithId } from './fileContext';
+import { FileId, FileWithId, OperationType, FileOperation } from './fileContext';
 
 declare global {
   namespace FileIdSafety {
@@ -31,14 +31,8 @@ declare global {
   }
 }
 
-// Module augmentation for stricter type checking on dangerous functions
-declare module '../utils/toolOperationTracker' {
-  export const createOperation: <TParams = void>(
-    operationType: string,
-    params: TParams,
-    selectedFiles: FileWithId[] // Must be FileWithId, not File[]
-  ) => { operation: FileOperation; operationId: string; fileId: string };
-}
+// Note: Module augmentation removed to prevent duplicate declaration
+// The actual implementation in toolOperationTracker.ts enforces FileWithId usage
 
 // Augment FileContext types to prevent bypassing FileWithId
 declare module '../contexts/FileContext' {
diff --git a/frontend/src/utils/toolOperationTracker.ts b/frontend/src/utils/toolOperationTracker.ts
deleted file mode 100644
index c58e3bf57..000000000
--- a/frontend/src/utils/toolOperationTracker.ts
+++ /dev/null
@@ -1,31 +0,0 @@
-import { FileOperation, FileWithId, safeGetFileId, FileId } from '../types/fileContext';
-
-/**
- * Creates operation tracking data for FileContext integration
- */
-export const createOperation = <TParams = void>(
-  operationType: string,
-  params: TParams,
-  selectedFiles: FileWithId[]
-): { operation: FileOperation; operationId: string; fileId: string } => {
-  const operationId = `${operationType}-${Date.now()}-${Math.random().toString(36).substr(2, 9)}`;
-  
-  // Use proper FileIds instead of file.name - fixed dangerous pattern
-  const fileIds = selectedFiles.map(file => file.fileId);
-  const fileId = fileIds.join(',');
-
-  const operation: FileOperation = {
-    id: operationId,
-    type: operationType,
-    timestamp: Date.now(),
-    fileIds, // Now properly uses FileId[] instead of file.name[]
-    status: 'pending',
-    metadata: {
-      originalFileName: selectedFiles[0]?.name,
-      parameters: params,
-      fileSize: selectedFiles.reduce((sum, f) => sum + f.size, 0)
-    }
-  };
-
-  return { operation, operationId, fileId };
-};