diff --git a/frontend/src/contexts/FilesModalContext.tsx b/frontend/src/contexts/FilesModalContext.tsx
index 703c8b05c..e850fa4dd 100644
--- a/frontend/src/contexts/FilesModalContext.tsx
+++ b/frontend/src/contexts/FilesModalContext.tsx
@@ -2,6 +2,7 @@ import React, { createContext, useContext, useState, useCallback, useMemo } from
 import { useFileHandler } from '../hooks/useFileHandler';
 import { useFileActions } from './FileContext';
 import { StirlingFileStub } from '../types/fileContext';
+import { fileStorage } from '../services/fileStorage';
 
 interface FilesModalContextType {
   isFilesModalOpen: boolean;
@@ -47,23 +48,34 @@ export const FilesModalProvider: React.FC<{ children: React.ReactNode }> = ({ ch
     closeFilesModal();
   }, [addFiles, closeFilesModal, insertAfterPage, customHandler]);
 
-  const handleRecentFileSelect = useCallback((stirlingFileStubs: StirlingFileStub[]) => {
+  const handleRecentFileSelect = useCallback(async (stirlingFileStubs: StirlingFileStub[]) => {
     if (customHandler) {
-      // For custom handlers, we need to load the actual files first
-      // This is a bit complex - for now, let's not support custom handlers with stubs
-      console.warn('Custom handlers not yet supported for StirlingFileStub selection');
-      closeFilesModal();
-      return;
-    }
-
-    // Use the new addStirlingFileStubs action to preserve metadata
-    if (actions.addStirlingFileStubs) {
-      actions.addStirlingFileStubs(stirlingFileStubs, { selectFiles: true });
+      // Load the actual files from storage for custom handler
+      try {
+        const loadedFiles: File[] = [];
+        for (const stub of stirlingFileStubs) {
+          const stirlingFile = await fileStorage.getStirlingFile(stub.id);
+          if (stirlingFile) {
+            loadedFiles.push(stirlingFile);
+          }
+        }
+        
+        if (loadedFiles.length > 0) {
+          customHandler(loadedFiles, insertAfterPage);
+        }
+      } catch (error) {
+        console.error('Failed to load files for custom handler:', error);
+      }
     } else {
-      console.error('addStirlingFileStubs action not available');
+      // Normal case - use addStirlingFileStubs to preserve metadata
+      if (actions.addStirlingFileStubs) {
+        actions.addStirlingFileStubs(stirlingFileStubs, { selectFiles: true });
+      } else {
+        console.error('addStirlingFileStubs action not available');
+      }
     }
     closeFilesModal();
-  }, [actions.addStirlingFileStubs, closeFilesModal, customHandler]);
+  }, [actions.addStirlingFileStubs, closeFilesModal, customHandler, insertAfterPage]);
 
   const setModalCloseCallback = useCallback((callback: () => void) => {
     setOnModalClose(() => callback);
diff --git a/frontend/src/contexts/file/fileActions.ts b/frontend/src/contexts/file/fileActions.ts
index cd61f42e7..de5c32370 100644
--- a/frontend/src/contexts/file/fileActions.ts
+++ b/frontend/src/contexts/file/fileActions.ts
@@ -545,6 +545,31 @@ export async function addStirlingFileStubs(
         record.insertAfterPageId = options.insertAfterPageId;
       }
 
+      // Check if processedFile data needs regeneration for proper Page Editor support
+      if (stirlingFile.type.startsWith('application/pdf')) {
+        const needsProcessing = !record.processedFile || 
+                                !record.processedFile.pages || 
+                                record.processedFile.pages.length === 0 ||
+                                record.processedFile.totalPages !== record.processedFile.pages.length;
+        
+        if (needsProcessing) {
+          if (DEBUG) console.log(`📄 addStirlingFileStubs: Regenerating processedFile for ${record.name}`);
+          try {
+            // Generate basic processedFile structure with page count
+            const result = await generateThumbnailWithMetadata(stirlingFile);
+            record.processedFile = createProcessedFile(result.pageCount, result.thumbnail);
+            record.thumbnailUrl = result.thumbnail; // Update thumbnail if needed
+            if (DEBUG) console.log(`📄 addStirlingFileStubs: Regenerated processedFile for ${record.name} with ${result.pageCount} pages`);
+          } catch (error) {
+            if (DEBUG) console.warn(`📄 addStirlingFileStubs: Failed to regenerate processedFile for ${record.name}:`, error);
+            // Ensure we have at least basic structure
+            if (!record.processedFile) {
+              record.processedFile = createProcessedFile(1); // Fallback to 1 page
+            }
+          }
+        }
+      }
+
       existingQuickKeys.add(stub.quickKey || '');
       validStubs.push(record);
       loadedFiles.push(stirlingFile);
diff --git a/frontend/src/hooks/useFileHandler.ts b/frontend/src/hooks/useFileHandler.ts
index 5996b75fe..c29b5bd36 100644
--- a/frontend/src/hooks/useFileHandler.ts
+++ b/frontend/src/hooks/useFileHandler.ts
@@ -4,9 +4,11 @@ import { useFileActions } from '../contexts/FileContext';
 export const useFileHandler = () => {
   const { actions } = useFileActions();
 
-  const addFiles = useCallback(async (files: File[]) => {
+  const addFiles = useCallback(async (files: File[], options: { insertAfterPageId?: string; selectFiles?: boolean } = {}) => {
+    // Merge default options with passed options - passed options take precedence
+    const mergedOptions = { selectFiles: true, ...options };
     // Let FileContext handle deduplication with quickKey logic
-    await actions.addFiles(files, { selectFiles: true });
+    await actions.addFiles(files, mergedOptions);
   }, [actions.addFiles]);
 
   return {