diff --git a/frontend/src/components/pageEditor/PageEditor.tsx b/frontend/src/components/pageEditor/PageEditor.tsx
index 1711e5627..39c6c706b 100644
--- a/frontend/src/components/pageEditor/PageEditor.tsx
+++ b/frontend/src/components/pageEditor/PageEditor.tsx
@@ -385,6 +385,19 @@ const PageEditor = ({
     undoManagerRef.current.executeCommand(pageBreakCommand);
   }, [selectedPageNumbers, displayDocument]);
 
+  const handleInsertFiles = useCallback(async (files: File[], insertAfterPage: number) => {
+    if (!displayDocument || files.length === 0) return;
+
+    try {
+      const targetPage = displayDocument.pages.find(p => p.pageNumber === insertAfterPage);
+      if (!targetPage) return;
+      
+      await actions.addFiles(files, { insertAfterPageId: targetPage.id });
+    } catch (error) {
+      console.error('Failed to insert files:', error);
+    }
+  }, [displayDocument, actions]);
+
   const handleSelectAll = useCallback(() => {
     if (!displayDocument) return;
     const allPageNumbers = Array.from({ length: displayDocument.pages.length }, (_, i) => i + 1);
@@ -416,12 +429,7 @@ const PageEditor = ({
   const getSourceFiles = useCallback((): Map<string, File> | null => {
     const sourceFiles = new Map<string, File>();
 
-    // Check if we have multiple files by looking at active file IDs
-    if (activeFileIds.length <= 1) {
-      return null; // Use single-file export method
-    }
-
-    // Collect all source files
+    // Always include original files
     activeFileIds.forEach(fileId => {
       const file = selectors.getFile(fileId);
       if (file) {
@@ -429,6 +437,14 @@ const PageEditor = ({
       }
     });
 
+    // Use multi-file export if we have multiple original files
+    const hasInsertedFiles = false;
+    const hasMultipleOriginalFiles = activeFileIds.length > 1;
+    
+    if (!hasInsertedFiles && !hasMultipleOriginalFiles) {
+      return null; // Use single-file export method
+    }
+
     return sourceFiles.size > 0 ? sourceFiles : null;
   }, [activeFileIds, selectors]);
 
@@ -755,6 +771,7 @@ const PageEditor = ({
                 pdfDocument={displayDocument}
                 setPdfDocument={setEditedDocument}
                 splitPositions={splitPositions}
+                onInsertFiles={handleInsertFiles}
               />
             )}
           />
diff --git a/frontend/src/components/pageEditor/PageThumbnail.tsx b/frontend/src/components/pageEditor/PageThumbnail.tsx
index bc8d9c467..e988b1557 100644
--- a/frontend/src/components/pageEditor/PageThumbnail.tsx
+++ b/frontend/src/components/pageEditor/PageThumbnail.tsx
@@ -6,9 +6,11 @@ import RotateLeftIcon from '@mui/icons-material/RotateLeft';
 import RotateRightIcon from '@mui/icons-material/RotateRight';
 import DeleteIcon from '@mui/icons-material/Delete';
 import ContentCutIcon from '@mui/icons-material/ContentCut';
+import AddIcon from '@mui/icons-material/Add';
 import { draggable, dropTargetForElements } from '@atlaskit/pragmatic-drag-and-drop/element/adapter';
 import { PDFPage, PDFDocument } from '../../types/pageEditor';
 import { useThumbnailGeneration } from '../../hooks/useThumbnailGeneration';
+import { useFilesModalContext } from '../../contexts/FilesModalContext';
 import styles from './PageEditor.module.css';
 
 
@@ -35,6 +37,7 @@ interface PageThumbnailProps {
   pdfDocument: PDFDocument;
   setPdfDocument: (doc: PDFDocument) => void;
   splitPositions: Set<number>;
+  onInsertFiles?: (files: File[], insertAfterPage: number) => void;
 }
 
 const PageThumbnail: React.FC<PageThumbnailProps> = ({
@@ -60,6 +63,7 @@ const PageThumbnail: React.FC<PageThumbnailProps> = ({
   pdfDocument,
   setPdfDocument,
   splitPositions,
+  onInsertFiles,
 }: PageThumbnailProps) => {
   const [isDragging, setIsDragging] = useState(false);
   const [isMouseDown, setIsMouseDown] = useState(false);
@@ -67,6 +71,7 @@ const PageThumbnail: React.FC<PageThumbnailProps> = ({
   const dragElementRef = useRef<HTMLDivElement>(null);
   const [thumbnailUrl, setThumbnailUrl] = useState<string | null>(page.thumbnail);
   const { getThumbnailFromCache, requestThumbnail } = useThumbnailGeneration();
+  const { openFilesModal } = useFilesModalContext();
 
   // Calculate document aspect ratio from first non-blank page
   const getDocumentAspectRatio = useCallback(() => {
@@ -224,6 +229,27 @@ const PageThumbnail: React.FC<PageThumbnailProps> = ({
     onSetStatus(`Split marker ${action} after position ${index + 1}`);
   }, [index, splitPositions, onExecuteCommand, onSetStatus, createSplitCommand]);
 
+  const handleInsertFileAfter = useCallback((e: React.MouseEvent) => {
+    e.stopPropagation();
+    
+    if (onInsertFiles) {
+      // Open file manager modal with custom handler for page insertion
+      openFilesModal({ 
+        insertAfterPage: page.pageNumber,
+        customHandler: (files: File[], insertAfterPage?: number) => {
+          if (insertAfterPage !== undefined) {
+            onInsertFiles(files, insertAfterPage);
+          }
+        }
+      });
+      onSetStatus(`Select files to insert after page ${page.pageNumber}`);
+    } else {
+      // Fallback to normal file handling
+      openFilesModal({ insertAfterPage: page.pageNumber });
+      onSetStatus(`Select files to insert after page ${page.pageNumber}`);
+    }
+  }, [openFilesModal, page.pageNumber, onSetStatus, onInsertFiles]);
+
   // Handle click vs drag differentiation
   const handleMouseDown = useCallback((e: React.MouseEvent) => {
     setIsMouseDown(true);
@@ -509,6 +535,17 @@ const PageThumbnail: React.FC<PageThumbnailProps> = ({
               </ActionIcon>
             </Tooltip>
           )}
+
+          <Tooltip label="Insert File After">
+            <ActionIcon
+              size="md"
+              variant="subtle"
+              style={{ color: 'var(--mantine-color-dimmed)' }}
+              onClick={handleInsertFileAfter}
+            >
+              <AddIcon style={{ fontSize: 20 }} />
+            </ActionIcon>
+          </Tooltip>
         </div>
 
       </div>
diff --git a/frontend/src/components/pageEditor/commands/pageCommands.ts b/frontend/src/components/pageEditor/commands/pageCommands.ts
index c9364dc27..1b7cb0932 100644
--- a/frontend/src/components/pageEditor/commands/pageCommands.ts
+++ b/frontend/src/components/pageEditor/commands/pageCommands.ts
@@ -568,6 +568,268 @@ export class BulkPageBreakCommand extends DOMCommand {
   }
 }
 
+export class InsertFilesCommand extends DOMCommand {
+  private insertedPages: PDFPage[] = [];
+  private originalDocument: PDFDocument | null = null;
+  private fileDataMap = new Map<string, ArrayBuffer>(); // Store file data for thumbnail generation
+  private originalProcessedFile: any = null; // Store original ProcessedFile for undo
+  private insertedFileMap = new Map<string, File>(); // Store inserted files for export
+
+  constructor(
+    private files: File[],
+    private insertAfterPageNumber: number,
+    private getCurrentDocument: () => PDFDocument | null,
+    private setDocument: (doc: PDFDocument) => void,
+    private setSelectedPages: (pages: number[]) => void,
+    private getSelectedPages: () => number[],
+    private updateFileContext?: (updatedDocument: PDFDocument, insertedFiles?: Map<string, File>) => void
+  ) {
+    super();
+  }
+
+  async execute(): Promise<void> {
+    const currentDoc = this.getCurrentDocument();
+    if (!currentDoc || this.files.length === 0) return;
+
+    // Store original state for undo
+    this.originalDocument = {
+      ...currentDoc,
+      pages: currentDoc.pages.map(page => ({...page}))
+    };
+
+    try {
+      // Process each file to extract pages and wait for all to complete
+      const allNewPages: PDFPage[] = [];
+      
+      // Process all files and wait for their completion
+      const baseTimestamp = Date.now();
+      const extractionPromises = this.files.map(async (file, index) => {
+        const fileId = `inserted-${file.name}-${baseTimestamp + index}`;
+        // Store inserted file for export
+        this.insertedFileMap.set(fileId, file);
+        // Use base timestamp + index to ensure unique but predictable file IDs
+        return await this.extractPagesFromFile(file, baseTimestamp + index);
+      });
+      
+      const extractedPageArrays = await Promise.all(extractionPromises);
+      
+      // Flatten all extracted pages
+      for (const pages of extractedPageArrays) {
+        allNewPages.push(...pages);
+      }
+
+      if (allNewPages.length === 0) return;
+
+      // Find insertion point (after the specified page)
+      const insertIndex = this.insertAfterPageNumber; // Insert after page N means insert at index N
+
+      // Create new pages array with inserted pages
+      const newPages: PDFPage[] = [];
+      let pageNumberCounter = 1;
+
+      // Add pages before insertion point
+      for (let i = 0; i < insertIndex && i < currentDoc.pages.length; i++) {
+        const page = { ...currentDoc.pages[i], pageNumber: pageNumberCounter++ };
+        newPages.push(page);
+      }
+
+      // Add inserted pages
+      for (const newPage of allNewPages) {
+        const insertedPage: PDFPage = {
+          ...newPage,
+          pageNumber: pageNumberCounter++,
+          selected: false,
+          splitAfter: false
+        };
+        newPages.push(insertedPage);
+        this.insertedPages.push(insertedPage);
+      }
+
+      // Add remaining pages after insertion point
+      for (let i = insertIndex; i < currentDoc.pages.length; i++) {
+        const page = { ...currentDoc.pages[i], pageNumber: pageNumberCounter++ };
+        newPages.push(page);
+      }
+
+      // Update document
+      const updatedDocument: PDFDocument = {
+        ...currentDoc,
+        pages: newPages,
+        totalPages: newPages.length,
+      };
+
+      this.setDocument(updatedDocument);
+
+      // Update FileContext with the new document structure and inserted files
+      if (this.updateFileContext) {
+        this.updateFileContext(updatedDocument, this.insertedFileMap);
+      }
+
+      // Generate thumbnails for inserted pages (all files should be read by now)
+      this.generateThumbnailsForInsertedPages(updatedDocument);
+
+      // Maintain existing selection by mapping original selected pages to their new positions
+      const originalSelection = this.getSelectedPages();
+      const updatedSelection: number[] = [];
+      
+      originalSelection.forEach(originalPageNum => {
+        if (originalPageNum <= this.insertAfterPageNumber) {
+          // Pages before insertion point keep same number
+          updatedSelection.push(originalPageNum);
+        } else {
+          // Pages after insertion point are shifted by number of inserted pages
+          updatedSelection.push(originalPageNum + allNewPages.length);
+        }
+      });
+      
+      this.setSelectedPages(updatedSelection);
+
+    } catch (error) {
+      console.error('Failed to insert files:', error);
+      // Revert to original state if error occurs
+      if (this.originalDocument) {
+        this.setDocument(this.originalDocument);
+      }
+    }
+  }
+
+  private async generateThumbnailsForInsertedPages(updatedDocument: PDFDocument): Promise<void> {
+    try {
+      const { thumbnailGenerationService } = await import('../../../services/thumbnailGenerationService');
+      
+      // Group pages by file ID to generate thumbnails efficiently
+      const pagesByFileId = new Map<string, PDFPage[]>();
+      
+      for (const page of this.insertedPages) {
+        const fileId = page.id.substring(0, page.id.lastIndexOf('-page-'));
+        if (!pagesByFileId.has(fileId)) {
+          pagesByFileId.set(fileId, []);
+        }
+        pagesByFileId.get(fileId)!.push(page);
+      }
+      
+      // Generate thumbnails for each file
+      for (const [fileId, pages] of pagesByFileId) {
+        const arrayBuffer = this.fileDataMap.get(fileId);
+        
+        console.log('Generating thumbnails for file:', fileId);
+        console.log('Pages:', pages.length);
+        console.log('ArrayBuffer size:', arrayBuffer?.byteLength || 'undefined');
+        
+        if (arrayBuffer && arrayBuffer.byteLength > 0) {
+          // Extract page numbers for all pages from this file
+          const pageNumbers = pages.map(page => {
+            const pageNumMatch = page.id.match(/-page-(\d+)$/);
+            return pageNumMatch ? parseInt(pageNumMatch[1]) : 1;
+          });
+          
+          console.log('Generating thumbnails for page numbers:', pageNumbers);
+          
+          // Generate thumbnails for all pages from this file at once
+          const results = await thumbnailGenerationService.generateThumbnails(
+            fileId,
+            arrayBuffer,
+            pageNumbers,
+            { scale: 0.2, quality: 0.8 }
+          );
+          
+          console.log('Thumbnail generation results:', results.length, 'thumbnails generated');
+          
+          // Update pages with generated thumbnails
+          for (let i = 0; i < results.length && i < pages.length; i++) {
+            const result = results[i];
+            const page = pages[i];
+            
+            if (result.success) {
+              const pageIndex = updatedDocument.pages.findIndex(p => p.id === page.id);
+              if (pageIndex >= 0) {
+                updatedDocument.pages[pageIndex].thumbnail = result.thumbnail;
+                console.log('Updated thumbnail for page:', page.id);
+              }
+            }
+          }
+          
+          // Trigger re-render by updating the document
+          this.setDocument({ ...updatedDocument });
+        } else {
+          console.error('No valid ArrayBuffer found for file ID:', fileId);
+        }
+      }
+    } catch (error) {
+      console.error('Failed to generate thumbnails for inserted pages:', error);
+    }
+  }
+
+  private async extractPagesFromFile(file: File, baseTimestamp: number): Promise<PDFPage[]> {
+    return new Promise((resolve, reject) => {
+      const reader = new FileReader();
+      reader.onload = async (event) => {
+        try {
+          const arrayBuffer = event.target?.result as ArrayBuffer;
+          console.log('File reader onload - arrayBuffer size:', arrayBuffer?.byteLength || 'undefined');
+          
+          if (!arrayBuffer) {
+            reject(new Error('Failed to read file'));
+            return;
+          }
+
+          // Clone the ArrayBuffer before passing to PDF.js (it might consume it)
+          const clonedArrayBuffer = arrayBuffer.slice(0);
+          
+          // Use PDF.js via the worker manager to extract pages
+          const { pdfWorkerManager } = await import('../../../services/pdfWorkerManager');
+          const pdf = await pdfWorkerManager.createDocument(clonedArrayBuffer);
+          
+          const pageCount = pdf.numPages;
+          const pages: PDFPage[] = [];
+          const fileId = `inserted-${file.name}-${baseTimestamp}`;
+          
+          console.log('Original ArrayBuffer size:', arrayBuffer.byteLength);
+          console.log('Storing ArrayBuffer for fileId:', fileId, 'size:', arrayBuffer.byteLength);
+          
+          // Store the original ArrayBuffer for thumbnail generation
+          this.fileDataMap.set(fileId, arrayBuffer);
+          
+          console.log('After storing - fileDataMap size:', this.fileDataMap.size);
+          console.log('Stored value size:', this.fileDataMap.get(fileId)?.byteLength || 'undefined');
+          
+          for (let i = 1; i <= pageCount; i++) {
+            const pageId = `${fileId}-page-${i}`;
+            pages.push({
+              id: pageId,
+              pageNumber: i, // Will be renumbered in execute()
+              originalPageNumber: i,
+              thumbnail: null, // Will be generated after insertion
+              rotation: 0,
+              selected: false,
+              splitAfter: false,
+              isBlankPage: false
+            });
+          }
+          
+          // Clean up PDF document
+          pdfWorkerManager.destroyDocument(pdf);
+          
+          resolve(pages);
+        } catch (error) {
+          reject(error);
+        }
+      };
+      reader.onerror = () => reject(new Error('Failed to read file'));
+      reader.readAsArrayBuffer(file);
+    });
+  }
+
+  undo(): void {
+    if (!this.originalDocument) return;
+    this.setDocument(this.originalDocument);
+  }
+
+  get description(): string {
+    return `Insert ${this.files.length} file(s) after page ${this.insertAfterPageNumber}`;
+  }
+}
+
 // Simple undo manager for DOM commands
 export class UndoManager {
   private undoStack: DOMCommand[] = [];
@@ -585,6 +847,13 @@ export class UndoManager {
     this.onStateChange?.();
   }
 
+  // For async commands that need to be executed manually
+  addToUndoStack(command: DOMCommand): void {
+    this.undoStack.push(command);
+    this.redoStack = [];
+    this.onStateChange?.();
+  }
+
   undo(): boolean {
     const command = this.undoStack.pop();
     if (command) {
diff --git a/frontend/src/components/pageEditor/hooks/usePageDocument.ts b/frontend/src/components/pageEditor/hooks/usePageDocument.ts
index 837ac4720..5a9d13f9f 100644
--- a/frontend/src/components/pageEditor/hooks/usePageDocument.ts
+++ b/frontend/src/components/pageEditor/hooks/usePageDocument.ts
@@ -49,33 +49,41 @@ export function usePageDocument(): PageDocumentHook {
             .map(id => (selectors.getFileRecord(id)?.name ?? 'file').replace(/\.pdf$/i, ''))
             .join(' + ');
 
-    // Debug logging for merged document creation
-    console.log(`🎬 PageEditor: Building merged document for ${name} with ${activeFileIds.length} files`);
+    // Build page insertion map from files with insertion positions
+    const insertionMap = new Map<string, string[]>(); // insertAfterPageId -> fileIds
+    const originalFileIds: string[] = [];
     
-    // Collect pages from ALL active files, not just the primary file
+    activeFileIds.forEach(fileId => {
+      const record = selectors.getFileRecord(fileId);
+      if (record?.insertAfterPageId !== undefined) {
+        if (!insertionMap.has(record.insertAfterPageId)) {
+          insertionMap.set(record.insertAfterPageId, []);
+        }
+        insertionMap.get(record.insertAfterPageId)!.push(fileId);
+      } else {
+        originalFileIds.push(fileId);
+      }
+    });
+    
+    // Build pages by interleaving original pages with insertions
     let pages: PDFPage[] = [];
     let totalPageCount = 0;
     
-    activeFileIds.forEach((fileId, fileIndex) => {
+    // Helper function to create pages from a file
+    const createPagesFromFile = (fileId: string, startPageNumber: number): PDFPage[] => {
       const fileRecord = selectors.getFileRecord(fileId);
       if (!fileRecord) {
-        console.warn(`🎬 PageEditor: No record found for file ${fileId}`);
-        return;
+        return [];
       }
       
       const processedFile = fileRecord.processedFile;
-      console.log(`🎬 PageEditor: Processing file ${fileIndex + 1}/${activeFileIds.length} (${fileRecord.name})`);
-      console.log(`🎬 ProcessedFile exists:`, !!processedFile);
-      console.log(`🎬 ProcessedFile pages:`, processedFile?.pages?.length || 0);
-      console.log(`🎬 ProcessedFile totalPages:`, processedFile?.totalPages || 'unknown');
-      
       let filePages: PDFPage[] = [];
       
       if (processedFile?.pages && processedFile.pages.length > 0) {
         // Use fully processed pages with thumbnails
         filePages = processedFile.pages.map((page, pageIndex) => ({
           id: `${fileId}-${page.pageNumber}`,
-          pageNumber: totalPageCount + pageIndex + 1,
+          pageNumber: startPageNumber + pageIndex,
           thumbnail: page.thumbnail || null,
           rotation: page.rotation || 0,
           selected: false,
@@ -85,30 +93,62 @@ export function usePageDocument(): PageDocumentHook {
         }));
       } else if (processedFile?.totalPages) {
         // Fallback: create pages without thumbnails but with correct count
-        console.log(`🎬 PageEditor: Creating placeholder pages for ${fileRecord.name} (${processedFile.totalPages} pages)`);
         filePages = Array.from({ length: processedFile.totalPages }, (_, pageIndex) => ({
           id: `${fileId}-${pageIndex + 1}`,
-          pageNumber: totalPageCount + pageIndex + 1,
+          pageNumber: startPageNumber + pageIndex,
           originalPageNumber: pageIndex + 1,
           originalFileId: fileId,
           rotation: 0,
-          thumbnail: null, // Will be generated later
+          thumbnail: null,
           selected: false,
           splitAfter: false,
         }));
       }
       
-      pages = pages.concat(filePages);
-      totalPageCount += filePages.length;
+      return filePages;
+    };
+
+    // Collect all pages from original files (without renumbering yet)
+    const originalFilePages: PDFPage[] = [];
+    originalFileIds.forEach(fileId => {
+      const filePages = createPagesFromFile(fileId, 1); // Temporary numbering
+      originalFilePages.push(...filePages);
     });
+    
+    // Start with all original pages numbered sequentially  
+    pages = originalFilePages.map((page, index) => ({
+      ...page,
+      pageNumber: index + 1
+    }));
+    
+    // Process each insertion by finding the page ID and inserting after it
+    for (const [insertAfterPageId, fileIds] of insertionMap.entries()) {
+      const targetPageIndex = pages.findIndex(p => p.id === insertAfterPageId);
+      
+      if (targetPageIndex === -1) continue;
+      
+      // Collect all pages to insert
+      const allNewPages: PDFPage[] = [];
+      fileIds.forEach(fileId => {
+        const insertedPages = createPagesFromFile(fileId, 1);
+        allNewPages.push(...insertedPages);
+      });
+      
+      // Insert all new pages after the target page
+      pages.splice(targetPageIndex + 1, 0, ...allNewPages);
+      
+      // Renumber all pages after insertion
+      pages.forEach((page, index) => {
+        page.pageNumber = index + 1;
+      });
+    }
+    
+    totalPageCount = pages.length;
 
     if (pages.length === 0) {
-      console.warn('🎬 PageEditor: No pages found in any files');
       return null;
     }
 
-    console.log(`🎬 PageEditor: Created merged document with ${pages.length} total pages`);
-
     const mergedDoc: PDFDocument = {
       id: activeFileIds.join('-'),
       name,
diff --git a/frontend/src/components/tools/shared/FileStatusIndicator.tsx b/frontend/src/components/tools/shared/FileStatusIndicator.tsx
index 20e7c4d7a..f54f66219 100644
--- a/frontend/src/components/tools/shared/FileStatusIndicator.tsx
+++ b/frontend/src/components/tools/shared/FileStatusIndicator.tsx
@@ -25,7 +25,7 @@ const FileStatusIndicator = ({
         {t("files.noFiles", "No files uploaded. ")}{" "}
         <Anchor
           size="sm"
-          onClick={openFilesModal}
+          onClick={() => openFilesModal()}
           style={{ cursor: 'pointer', display: 'inline-flex', alignItems: 'center', gap: '4px' }}
         >
           <FolderIcon style={{ fontSize: '14px' }} />
@@ -42,7 +42,7 @@ const FileStatusIndicator = ({
         {t("files.selectFromWorkbench", "Select files from the workbench or ") + " "}
         <Anchor
           size="sm"
-          onClick={openFilesModal}
+          onClick={() => openFilesModal()}
           style={{ cursor: 'pointer', display: 'inline-flex', alignItems: 'center', gap: '4px' }}
         >
           <FolderIcon style={{ fontSize: '14px' }} />
diff --git a/frontend/src/contexts/FileContext.tsx b/frontend/src/contexts/FileContext.tsx
index 44adf6b28..285291539 100644
--- a/frontend/src/contexts/FileContext.tsx
+++ b/frontend/src/contexts/FileContext.tsx
@@ -73,8 +73,8 @@ function FileContextInner({
   }, []);
 
   // File operations using unified addFiles helper with persistence
-  const addRawFiles = useCallback(async (files: File[]): Promise<File[]> => {
-    const addedFilesWithIds = await addFiles('raw', { files }, stateRef, filesRef, dispatch, lifecycleManager);
+  const addRawFiles = useCallback(async (files: File[], options?: { insertAfterPageId?: string }): Promise<File[]> => {
+    const addedFilesWithIds = await addFiles('raw', { files, ...options }, stateRef, filesRef, dispatch, lifecycleManager);
     
     // Persist to IndexedDB if enabled
     if (indexedDB && enablePersistence && addedFilesWithIds.length > 0) {
diff --git a/frontend/src/contexts/FilesModalContext.tsx b/frontend/src/contexts/FilesModalContext.tsx
index d7183eabf..2b210ce89 100644
--- a/frontend/src/contexts/FilesModalContext.tsx
+++ b/frontend/src/contexts/FilesModalContext.tsx
@@ -4,7 +4,7 @@ import { FileMetadata } from '../types/file';
 
 interface FilesModalContextType {
   isFilesModalOpen: boolean;
-  openFilesModal: () => void;
+  openFilesModal: (options?: { insertAfterPage?: number; customHandler?: (files: File[], insertAfterPage?: number) => void }) => void;
   closeFilesModal: () => void;
   onFileSelect: (file: File) => void;
   onFilesSelect: (files: File[]) => void;
@@ -19,30 +19,55 @@ export const FilesModalProvider: React.FC<{ children: React.ReactNode }> = ({ ch
   const { addToActiveFiles, addMultipleFiles, addStoredFiles } = useFileHandler();
   const [isFilesModalOpen, setIsFilesModalOpen] = useState(false);
   const [onModalClose, setOnModalClose] = useState<(() => void) | undefined>();
+  const [insertAfterPage, setInsertAfterPage] = useState<number | undefined>();
+  const [customHandler, setCustomHandler] = useState<((files: File[], insertAfterPage?: number) => void) | undefined>();
 
-  const openFilesModal = useCallback(() => {
+  const openFilesModal = useCallback((options?: { insertAfterPage?: number; customHandler?: (files: File[], insertAfterPage?: number) => void }) => {
+    setInsertAfterPage(options?.insertAfterPage);
+    setCustomHandler(() => options?.customHandler);
     setIsFilesModalOpen(true);
   }, []);
 
   const closeFilesModal = useCallback(() => {
     setIsFilesModalOpen(false);
+    setInsertAfterPage(undefined); // Clear insertion position
+    setCustomHandler(undefined); // Clear custom handler
     onModalClose?.();
   }, [onModalClose]);
 
   const handleFileSelect = useCallback((file: File) => {
-    addToActiveFiles(file);
+    if (customHandler) {
+      // Use custom handler for special cases (like page insertion)
+      customHandler([file], insertAfterPage);
+    } else {
+      // Use normal file handling
+      addToActiveFiles(file);
+    }
     closeFilesModal();
-  }, [addToActiveFiles, closeFilesModal]);
+  }, [addToActiveFiles, closeFilesModal, insertAfterPage, customHandler]);
 
   const handleFilesSelect = useCallback((files: File[]) => {
-    addMultipleFiles(files);
+    if (customHandler) {
+      // Use custom handler for special cases (like page insertion)
+      customHandler(files, insertAfterPage);
+    } else {
+      // Use normal file handling
+      addMultipleFiles(files);
+    }
     closeFilesModal();
-  }, [addMultipleFiles, closeFilesModal]);
+  }, [addMultipleFiles, closeFilesModal, insertAfterPage, customHandler]);
 
   const handleStoredFilesSelect = useCallback((filesWithMetadata: Array<{ file: File; originalId: string; metadata: FileMetadata }>) => {
-    addStoredFiles(filesWithMetadata);
+    if (customHandler) {
+      // Use custom handler for special cases (like page insertion)
+      const files = filesWithMetadata.map(item => item.file);
+      customHandler(files, insertAfterPage);
+    } else {
+      // Use normal file handling
+      addStoredFiles(filesWithMetadata);
+    }
     closeFilesModal();
-  }, [addStoredFiles, closeFilesModal]);
+  }, [addStoredFiles, closeFilesModal, insertAfterPage, customHandler]);
 
   const setModalCloseCallback = useCallback((callback: () => void) => {
     setOnModalClose(() => callback);
diff --git a/frontend/src/contexts/file/fileActions.ts b/frontend/src/contexts/file/fileActions.ts
index 948b4f011..c8efac3db 100644
--- a/frontend/src/contexts/file/fileActions.ts
+++ b/frontend/src/contexts/file/fileActions.ts
@@ -84,6 +84,9 @@ interface AddFileOptions {
   
   // For 'stored' files
   filesWithMetadata?: Array<{ file: File; originalId: FileId; metadata: FileMetadata }>;
+  
+  // Insertion position
+  insertAfterPageId?: string;
 }
 
 /**
@@ -164,6 +167,11 @@ export async function addFiles(
           }
         }
         
+        // Store insertion position if provided
+        if (options.insertAfterPageId !== undefined) {
+          record.insertAfterPageId = options.insertAfterPageId;
+        }
+        
         // Create initial processedFile metadata with page count
         if (pageCount > 0) {
           record.processedFile = createProcessedFile(pageCount, thumbnail);
diff --git a/frontend/src/types/fileContext.ts b/frontend/src/types/fileContext.ts
index 0425031c5..653909568 100644
--- a/frontend/src/types/fileContext.ts
+++ b/frontend/src/types/fileContext.ts
@@ -55,6 +55,7 @@ export interface FileRecord {
   blobUrl?: string;
   createdAt?: number;
   processedFile?: ProcessedFileMetadata;
+  insertAfterPageId?: string; // Page ID after which this file should be inserted
   isPinned?: boolean;
   // Note: File object stored in provider ref, not in state
 }
@@ -216,7 +217,7 @@ export type FileContextAction =
 
 export interface FileContextActions {
   // File management - lightweight actions only
-  addFiles: (files: File[]) => Promise<File[]>;
+  addFiles: (files: File[], options?: { insertAfterPageId?: string }) => 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) => Promise<void>;