diff --git a/ui/desktop/src/components/ChatInput.tsx b/ui/desktop/src/components/ChatInput.tsx
index 1f15d921a8db..13ab9b9de1e9 100644
--- a/ui/desktop/src/components/ChatInput.tsx
+++ b/ui/desktop/src/components/ChatInput.tsx
@@ -1239,7 +1239,7 @@ export default function ChatInput({
       {/* Secondary actions and controls row below input */}
       <div className="flex flex-row items-center gap-1 p-2 relative">
         {/* Directory path */}
-        <DirSwitcher hasMessages={messages.length > 0} className="mr-0" />
+        <DirSwitcher className="mr-0" />
         <div className="w-px h-4 bg-border-default mx-2" />
 
         {/* Attach button */}
diff --git a/ui/desktop/src/components/bottom_menu/DirSwitcher.tsx b/ui/desktop/src/components/bottom_menu/DirSwitcher.tsx
index c51bea91c9b7..4bf199988d39 100644
--- a/ui/desktop/src/components/bottom_menu/DirSwitcher.tsx
+++ b/ui/desktop/src/components/bottom_menu/DirSwitcher.tsx
@@ -3,22 +3,14 @@ import { FolderDot } from 'lucide-react';
 import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from '../ui/Tooltip';
 
 interface DirSwitcherProps {
-  hasMessages?: boolean;
   className?: string;
 }
 
-export const DirSwitcher: React.FC<DirSwitcherProps> = ({
-  hasMessages = false,
-  className = '',
-}) => {
+export const DirSwitcher: React.FC<DirSwitcherProps> = ({ className = '' }) => {
   const [isTooltipOpen, setIsTooltipOpen] = useState(false);
 
   const handleDirectoryChange = async () => {
-    if (hasMessages) {
-      window.electron.directoryChooser();
-    } else {
-      window.electron.directoryChooser(true);
-    }
+    window.electron.directoryChooser(true);
   };
 
   return (
diff --git a/ui/desktop/src/main.ts b/ui/desktop/src/main.ts
index 81e828610df2..589acd2d4b64 100644
--- a/ui/desktop/src/main.ts
+++ b/ui/desktop/src/main.ts
@@ -944,8 +944,60 @@ const buildRecentFilesMenu = () => {
 const openDirectoryDialog = async (
   replaceWindow: boolean = false
 ): Promise<OpenDialogReturnValue> => {
+  // Get the current working directory from the focused window
+  let defaultPath: string | undefined;
+  const currentWindow = BrowserWindow.getFocusedWindow();
+
+  if (currentWindow) {
+    try {
+      const currentWorkingDir = await currentWindow.webContents.executeJavaScript(
+        `window.appConfig ? window.appConfig.get('GOOSE_WORKING_DIR') : null`
+      );
+
+      if (currentWorkingDir && typeof currentWorkingDir === 'string') {
+        // Verify the directory exists before using it as default
+        try {
+          const stats = fsSync.lstatSync(currentWorkingDir);
+          if (stats.isDirectory()) {
+            defaultPath = currentWorkingDir;
+          }
+        } catch (error) {
+          if (error && typeof error === 'object' && 'code' in error) {
+            const fsError = error as { code?: string; message?: string };
+            if (
+              fsError.code === 'ENOENT' ||
+              fsError.code === 'EACCES' ||
+              fsError.code === 'EPERM'
+            ) {
+              console.warn(
+                `Current working directory not accessible (${fsError.code}): ${currentWorkingDir}, falling back to home directory`
+              );
+              defaultPath = os.homedir();
+            } else {
+              console.warn(
+                `Unexpected filesystem error (${fsError.code}) for directory ${currentWorkingDir}:`,
+                fsError.message
+              );
+              defaultPath = os.homedir();
+            }
+          } else {
+            console.warn(`Unexpected error checking directory ${currentWorkingDir}:`, error);
+            defaultPath = os.homedir();
+          }
+        }
+      }
+    } catch (error) {
+      console.warn('Failed to get current working directory from window:', error);
+    }
+  }
+
+  if (!defaultPath) {
+    defaultPath = os.homedir();
+  }
+
   const result = (await dialog.showOpenDialog({
     properties: ['openFile', 'openDirectory', 'createDirectory'],
+    defaultPath: defaultPath,
   })) as unknown as OpenDialogReturnValue;
 
   if (!result.canceled && result.filePaths.length > 0) {