diff --git a/frontend/src/contexts/FileContext.tsx b/frontend/src/contexts/FileContext.tsx
index 05fdc9a9a..0698310b4 100644
--- a/frontend/src/contexts/FileContext.tsx
+++ b/frontend/src/contexts/FileContext.tsx
@@ -25,7 +25,7 @@ import {
 // Import modular components
 import { fileContextReducer, initialFileContextState } from './file/FileReducer';
 import { createFileSelectors } from './file/fileSelectors';
-import { addFiles, consumeFiles, createFileActions } from './file/fileActions';
+import { AddedFile, addFiles, consumeFiles, createFileActions } from './file/fileActions';
 import { FileLifecycleManager } from './file/lifecycle';
 import { FileStateContext, FileActionsContext } from './file/contexts';
 import { IndexedDBProvider, useIndexedDB } from './IndexedDBContext';
@@ -72,9 +72,21 @@ function FileContextInner({
     dispatch({ type: 'SET_UNSAVED_CHANGES', payload: { hasChanges } });
   }, []);
 
+  const selectFiles = (addedFilesWithIds: AddedFile[]) => {
+    const currentSelection = stateRef.current.ui.selectedFileIds;
+    const newFileIds = addedFilesWithIds.map(({ id }) => id);
+    dispatch({ type: 'SET_SELECTED_FILES', payload: { fileIds: [...currentSelection, ...newFileIds] } });
+  }
+
   // File operations using unified addFiles helper with persistence
-  const addRawFiles = useCallback(async (files: File[], options?: { insertAfterPageId?: string }): Promise<File[]> => {
+  const addRawFiles = useCallback(async (files: File[], options?: { insertAfterPageId?: string; selectFiles?: boolean }): Promise<File[]> => {
     const addedFilesWithIds = await addFiles('raw', { files, ...options }, stateRef, filesRef, dispatch, lifecycleManager);
+
+    // Auto-select the newly added files if requested
+    if (options?.selectFiles && addedFilesWithIds.length > 0) {
+      selectFiles(addedFilesWithIds);
+    }
+
     // Persist to IndexedDB if enabled
     if (indexedDB && enablePersistence && addedFilesWithIds.length > 0) {
       await Promise.all(addedFilesWithIds.map(async ({ file, id, thumbnail }) => {
@@ -94,8 +106,14 @@ function FileContextInner({
     return result.map(({ file }) => file);
   }, []);
 
-  const addStoredFiles = useCallback(async (filesWithMetadata: Array<{ file: File; originalId: FileId; metadata: any }>): Promise<File[]> => {
+  const addStoredFiles = useCallback(async (filesWithMetadata: Array<{ file: File; originalId: FileId; metadata: any }>, options?: { selectFiles?: boolean }): Promise<File[]> => {
     const result = await addFiles('stored', { filesWithMetadata }, stateRef, filesRef, dispatch, lifecycleManager);
+
+    // Auto-select the newly added files if requested
+    if (options?.selectFiles && result.length > 0) {
+      selectFiles(result);
+    }
+
     return result.map(({ file }) => file);
   }, []);
 
diff --git a/frontend/src/contexts/file/fileActions.ts b/frontend/src/contexts/file/fileActions.ts
index d0c565783..8d91f8855 100644
--- a/frontend/src/contexts/file/fileActions.ts
+++ b/frontend/src/contexts/file/fileActions.ts
@@ -88,6 +88,12 @@ interface AddFileOptions {
   insertAfterPageId?: string;
 }
 
+export interface AddedFile {
+  file: File;
+  id: FileId;
+  thumbnail?: string;
+}
+
 /**
  * Unified file addition helper - replaces addFiles/addProcessedFiles/addStoredFiles
  */
@@ -98,13 +104,13 @@ export async function addFiles(
   filesRef: React.MutableRefObject<Map<FileId, File>>,
   dispatch: React.Dispatch<FileContextAction>,
   lifecycleManager: FileLifecycleManager
-): Promise<Array<{ file: File; id: FileId; thumbnail?: string }>> {
+): Promise<AddedFile[]> {
   // Acquire mutex to prevent race conditions
   await addFilesMutex.lock();
 
   try {
   const fileRecords: FileRecord[] = [];
-  const addedFiles: Array<{ file: File; id: FileId; thumbnail?: string }> = [];
+  const addedFiles: AddedFile[] = [];
 
   // Build quickKey lookup from existing files for deduplication
   const existingQuickKeys = buildQuickKeySet(stateRef.current.files.byId);
diff --git a/frontend/src/hooks/useFileHandler.ts b/frontend/src/hooks/useFileHandler.ts
index 475affa6f..8c2a4e2a1 100644
--- a/frontend/src/hooks/useFileHandler.ts
+++ b/frontend/src/hooks/useFileHandler.ts
@@ -9,12 +9,12 @@ export const useFileHandler = () => {
 
   const addToActiveFiles = useCallback(async (file: File) => {
     // Let FileContext handle deduplication with quickKey logic
-    await actions.addFiles([file]);
+    await actions.addFiles([file], { selectFiles: true });
   }, [actions.addFiles]);
 
   const addMultipleFiles = useCallback(async (files: File[]) => {
     // Let FileContext handle deduplication with quickKey logic
-    await actions.addFiles(files);
+    await actions.addFiles(files, { selectFiles: true });
   }, [actions.addFiles]);
 
   // Add stored files preserving their original IDs to prevent session duplicates
@@ -25,7 +25,7 @@ export const useFileHandler = () => {
     });
 
     if (newFiles.length > 0) {
-      await actions.addStoredFiles(newFiles);
+      await actions.addStoredFiles(newFiles, { selectFiles: true });
     }
 
     console.log(`📁 Added ${newFiles.length} stored files (${filesWithMetadata.length - newFiles.length} skipped as duplicates)`);
diff --git a/frontend/src/types/fileContext.ts b/frontend/src/types/fileContext.ts
index 644b3dbfe..d9bd8751e 100644
--- a/frontend/src/types/fileContext.ts
+++ b/frontend/src/types/fileContext.ts
@@ -214,9 +214,9 @@ export type FileContextAction =
 
 export interface FileContextActions {
   // File management - lightweight actions only
-  addFiles: (files: File[], options?: { insertAfterPageId?: string }) => Promise<File[]>;
+  addFiles: (files: File[], options?: { insertAfterPageId?: string; selectFiles?: boolean }) => Promise<File[]>;
   addProcessedFiles: (filesWithThumbnails: Array<{ file: File; thumbnail?: string; pageCount?: number }>) => Promise<File[]>;
-  addStoredFiles: (filesWithMetadata: Array<{ file: File; originalId: FileId; metadata: FileMetadata }>) => Promise<File[]>;
+  addStoredFiles: (filesWithMetadata: Array<{ file: File; originalId: FileId; metadata: FileMetadata }>, options?: { selectFiles?: boolean }) => Promise<File[]>;
   removeFiles: (fileIds: FileId[], deleteFromStorage?: boolean) => Promise<void>;
   updateFileRecord: (id: FileId, updates: Partial<FileRecord>) => void;
   reorderFiles: (orderedFileIds: FileId[]) => void;