diff --git a/ui/desktop/src/main.ts b/ui/desktop/src/main.ts
index f33b6193..2384f258 100644
--- a/ui/desktop/src/main.ts
+++ b/ui/desktop/src/main.ts
@@ -266,6 +266,9 @@ const createChat = async (
   return mainWindow;
 };
 
+// Track tray instance
+let tray: Tray | null = null;
+
 const createTray = () => {
   const isDev = process.env.NODE_ENV === 'development';
   let iconPath: string;
@@ -276,7 +279,7 @@ const createTray = () => {
     iconPath = path.join(process.resourcesPath, 'images', 'iconTemplate.png');
   }
 
-  const tray = new Tray(iconPath);
+  tray = new Tray(iconPath);
 
   const contextMenu = Menu.buildFromTemplate([
     { label: 'Show Window', click: showWindow },
@@ -286,6 +289,11 @@ const createTray = () => {
 
   tray.setToolTip('Goose');
   tray.setContextMenu(contextMenu);
+
+  // On Windows, clicking the tray icon should show the window
+  if (process.platform === 'win32') {
+    tray.on('click', showWindow);
+  }
 };
 
 const showWindow = async () => {
@@ -336,16 +344,18 @@ const buildRecentFilesMenu = () => {
 
 const openDirectoryDialog = async (replaceWindow: boolean = false) => {
   const result = await dialog.showOpenDialog({
-    properties: ['openDirectory'],
+    properties: ['openFile', 'openDirectory'],
   });
 
   if (!result.canceled && result.filePaths.length > 0) {
     addRecentDir(result.filePaths[0]);
+    const currentWindow = BrowserWindow.getFocusedWindow();
+    const newWindow = await createChat(app, undefined, result.filePaths[0]);
     if (replaceWindow) {
-      BrowserWindow.getFocusedWindow().close();
+      currentWindow.close();
     }
-    createChat(app, undefined, result.filePaths[0]);
   }
+  return result;
 };
 
 // Global error handler
@@ -388,10 +398,15 @@ ipcMain.on('react-ready', (event) => {
   }
 });
 
+// Handle directory chooser
+ipcMain.handle('directory-chooser', (_, replace: boolean = false) => {
+  return openDirectoryDialog(replace);
+});
+
 // Add file/directory selection handler
 ipcMain.handle('select-file-or-directory', async () => {
   const result = await dialog.showOpenDialog({
-    properties: ['openFile', 'openDirectory'],
+    properties: process.platform === 'darwin' ? ['openFile', 'openDirectory'] : ['openFile'],
   });
 
   if (!result.canceled && result.filePaths.length > 0) {
@@ -539,9 +554,7 @@ app.whenReady().then(async () => {
     new MenuItem({
       label: 'Open Directory...',
       accelerator: 'CmdOrCtrl+O',
-      click() {
-        openDirectoryDialog();
-      },
+      click: () => openDirectoryDialog(),
     })
   );
 
@@ -614,10 +627,6 @@ app.whenReady().then(async () => {
     createChat(app, query, dir, version, resumeSessionId, botConfig);
   });
 
-  ipcMain.on('directory-chooser', (_, replace: boolean = false) => {
-    openDirectoryDialog(replace);
-  });
-
   ipcMain.on('notify', (event, data) => {
     console.log('NOTIFY', data);
     new Notification({ title: data.title, body: data.body }).show();
@@ -697,9 +706,10 @@ app.whenReady().then(async () => {
   });
 });
 
-// Quit when all windows are closed, except on macOS.
+// Quit when all windows are closed, except on macOS or if we have a tray icon.
 app.on('window-all-closed', () => {
-  if (process.platform !== 'darwin') {
+  // Only quit if we're not on macOS or don't have a tray icon
+  if (process.platform !== 'darwin' || !tray) {
     app.quit();
   }
 });
diff --git a/ui/desktop/src/preload.ts b/ui/desktop/src/preload.ts
index 8d91cca5..4809cb78 100644
--- a/ui/desktop/src/preload.ts
+++ b/ui/desktop/src/preload.ts
@@ -7,7 +7,7 @@ type ElectronAPI = {
   reactReady: () => void;
   getConfig: () => Record<string, any>;
   hideWindow: () => void;
-  directoryChooser: (replace: string) => void;
+  directoryChooser: (replace?: boolean) => Promise<Electron.OpenDialogReturnValue>;
   createChatWindow: (
     query?: string,
     dir?: string,
@@ -49,7 +49,7 @@ const electronAPI: ElectronAPI = {
   reactReady: () => ipcRenderer.send('react-ready'),
   getConfig: () => config,
   hideWindow: () => ipcRenderer.send('hide-window'),
-  directoryChooser: (replace: string) => ipcRenderer.send('directory-chooser', replace),
+  directoryChooser: (replace?: boolean) => ipcRenderer.invoke('directory-chooser', replace),
   createChatWindow: (
     query?: string,
     dir?: string,