diff --git a/src/App.tsx b/src/App.tsx
index a04c3cd9..c1f3719c 100644
--- a/src/App.tsx
+++ b/src/App.tsx
@@ -916,6 +916,7 @@ export default function App({ onLogout }: AppProps) {
               <FileTreePanel
                 workspaceAgentId={workspaceAgentId}
                 onOpenFile={openFile}
+                onAddToChat={(path, kind) => chatPanelRef.current?.addWorkspacePath(path, kind)}
                 lastChangedEvent={lastChangedEvent}
                 revealRequest={revealRequest}
                 onRemapOpenPaths={remapOpenPaths}
@@ -942,6 +943,7 @@ export default function App({ onLogout }: AppProps) {
                   <FileTreePanel
                     workspaceAgentId={workspaceAgentId}
                     onOpenFile={openFile}
+                    onAddToChat={(path, kind) => chatPanelRef.current?.addWorkspacePath(path, kind)}
                     lastChangedEvent={lastChangedEvent}
                     revealRequest={revealRequest}
                     onRemapOpenPaths={remapOpenPaths}
diff --git a/src/features/chat/ChatPanel.tsx b/src/features/chat/ChatPanel.tsx
index 65e65018..380fb9d1 100644
--- a/src/features/chat/ChatPanel.tsx
+++ b/src/features/chat/ChatPanel.tsx
@@ -49,6 +49,7 @@ interface ChatPanelProps {
 
 export interface ChatPanelHandle {
   focusInput: () => void;
+  addWorkspacePath: (path: string, kind: 'file' | 'directory') => Promise<void>;
 }
 
 /** Main chat panel with message list, infinite scroll, search, and input bar. */
@@ -119,7 +120,10 @@ export const ChatPanel = forwardRef<ChatPanelHandle, ChatPanelProps>(function Ch
 
   // Expose focusInput to parent
   useImperativeHandle(ref, () => ({
-    focusInput: () => inputBarRef.current?.focus()
+    focusInput: () => inputBarRef.current?.focus(),
+    addWorkspacePath: async (path: string, kind: 'file' | 'directory') => {
+      await inputBarRef.current?.addWorkspacePath(path, kind);
+    },
   }), []);
 
   // Clean up stale messageRefs when messages change
diff --git a/src/features/file-browser/FileTreePanel.test.tsx b/src/features/file-browser/FileTreePanel.test.tsx
index 5841740d..8e514c8f 100644
--- a/src/features/file-browser/FileTreePanel.test.tsx
+++ b/src/features/file-browser/FileTreePanel.test.tsx
@@ -53,6 +53,7 @@ function createDeferred<T>() {
 }
 
 const mockOnOpenFile = vi.fn();
+const mockOnAddToChat = vi.fn();
 const mockOnRemapOpenPaths = vi.fn();
 const mockOnCloseOpenPaths = vi.fn();
 
@@ -193,6 +194,50 @@ describe('FileTreePanel', () => {
     });
   });
 
+  describe('context menu add to chat', () => {
+    it('shows "Add to chat" for files and calls the callback', async () => {
+      render(
+        <FileTreePanel
+          onOpenFile={mockOnOpenFile}
+          onAddToChat={mockOnAddToChat}
+          onRemapOpenPaths={mockOnRemapOpenPaths}
+          onCloseOpenPaths={mockOnCloseOpenPaths}
+          collapsed={false}
+        />
+      );
+
+      fireEvent.contextMenu(screen.getByText('package.json'), new MouseEvent('contextmenu', { bubbles: true }));
+
+      await waitFor(() => {
+        expect(screen.getByText('Add to chat')).toBeInTheDocument();
+      });
+
+      fireEvent.click(screen.getByText('Add to chat'));
+
+      await waitFor(() => {
+        expect(mockOnAddToChat).toHaveBeenCalledWith('package.json', 'file');
+      });
+    });
+
+    it('does not show "Add to chat" for directories', async () => {
+      render(
+        <FileTreePanel
+          onOpenFile={mockOnOpenFile}
+          onAddToChat={mockOnAddToChat}
+          onRemapOpenPaths={mockOnRemapOpenPaths}
+          onCloseOpenPaths={mockOnCloseOpenPaths}
+          collapsed={false}
+        />
+      );
+
+      fireEvent.contextMenu(screen.getByText('src'), new MouseEvent('contextmenu', { bubbles: true }));
+
+      await waitFor(() => {
+        expect(screen.queryByText('Add to chat')).not.toBeInTheDocument();
+      });
+    });
+  });
+
   describe('context menu for deletion', () => {
     it('shows "Move to Trash" for default workspace', async () => {
       render(
diff --git a/src/features/file-browser/FileTreePanel.tsx b/src/features/file-browser/FileTreePanel.tsx
index e3661147..efcfe40a 100644
--- a/src/features/file-browser/FileTreePanel.tsx
+++ b/src/features/file-browser/FileTreePanel.tsx
@@ -6,7 +6,7 @@
  */
 
 import { useRef, useState, useCallback, useEffect } from 'react';
-import { PanelLeftClose, RefreshCw, Pencil, Trash2, RotateCcw, X } from 'lucide-react';
+import { PanelLeftClose, RefreshCw, Pencil, Trash2, RotateCcw, X, Paperclip } from 'lucide-react';
 import { FileTreeNode } from './FileTreeNode';
 import { useFileTree } from './hooks/useFileTree';
 import { ConfirmDialog } from '../../components/ConfirmDialog';
@@ -58,6 +58,7 @@ export interface FileTreeChangeEvent {
 interface FileTreePanelProps {
   workspaceAgentId: string;
   onOpenFile: (path: string) => void;
+  onAddToChat?: (path: string, kind: 'file' | 'directory') => Promise<void> | void;
   onRemapOpenPaths?: (fromPath: string, toPath: string, targetAgentId?: string) => void;
   onCloseOpenPaths?: (pathPrefix: string, targetAgentId?: string) => void;
   /** Called externally when a file changes (SSE) — refreshes affected directory. */
@@ -99,6 +100,7 @@ function isSameScopedSession<T extends ScopedSessionState>(current: T | null, ta
 export function FileTreePanel({
   workspaceAgentId = 'main',
   onOpenFile,
+  onAddToChat,
   onRemapOpenPaths,
   onCloseOpenPaths,
   lastChangedEvent,
@@ -667,6 +669,7 @@ export function FileTreePanel({
   const menuPath = menuEntry?.path || '';
   const menuInTrash = isTrashItemPath(menuPath);
   const showRestore = menuInTrash;
+  const showAddToChat = Boolean(onAddToChat && menuEntry?.type === 'file' && !menuPath.startsWith('.trash') && menuPath !== '.trash');
   const showRename = Boolean(menuEntry && menuPath !== '.trash');
   const showTrashAction = Boolean(menuEntry && !menuPath.startsWith('.trash') && menuPath !== '.trash');
 
@@ -791,6 +794,19 @@ export function FileTreePanel({
             </button>
           )}
 
+          {showAddToChat && (
+            <button
+              className="w-full px-3 py-1.5 text-left text-xs text-foreground hover:bg-muted/60 flex items-center gap-2"
+              onClick={() => {
+                setContextMenu(null);
+                void onAddToChat?.(menuEntry.path, 'file');
+              }}
+            >
+              <Paperclip size={12} />
+              Add to chat
+            </button>
+          )}
+
           {showRename && (
             <button
               className="w-full px-3 py-1.5 text-left text-xs text-foreground hover:bg-muted/60 flex items-center gap-2"
@@ -811,7 +827,7 @@ export function FileTreePanel({
             </button>
           )}
 
-          {!showRestore && !showRename && !showTrashAction && (
+          {!showRestore && !showAddToChat && !showRename && !showTrashAction && (
             <div className="px-3 py-1.5 text-xs text-muted-foreground">
               No actions
             </div>