diff --git a/electron/handlers/update.ts b/electron/handlers/update.ts
index 690c36d517..5e2200e519 100644
--- a/electron/handlers/update.ts
+++ b/electron/handlers/update.ts
@@ -39,6 +39,7 @@ export function handleAppUpdates() {
     })
     if (action.response === 0) {
       trayManager.destroyCurrentTray()
+      windowManager.closeQuickAskWindow()
       waitingToInstallVersion = _info?.version
       autoUpdater.quitAndInstall()
     }
diff --git a/electron/main.ts b/electron/main.ts
index cdc001af4c..47d4f19f46 100644
--- a/electron/main.ts
+++ b/electron/main.ts
@@ -1,4 +1,4 @@
-import { app, BrowserWindow, Tray } from 'electron'
+import { app, BrowserWindow } from 'electron'
 
 import { join } from 'path'
 /**
@@ -11,7 +11,7 @@ import { getAppConfigurations, log } from '@janhq/core/node'
  * IPC Handlers
  **/
 import { injectHandler } from './handlers/common'
-import { handleAppUpdates, waitingToInstallVersion } from './handlers/update'
+import { handleAppUpdates } from './handlers/update'
 import { handleAppIPCs } from './handlers/native'
 
 /**
@@ -96,7 +96,11 @@ app.once('quit', () => {
 
 app.once('window-all-closed', () => {
   // Feature Toggle for Quick Ask
-  if (getAppConfigurations().quick_ask && !waitingToInstallVersion) return
+  if (
+    getAppConfigurations().quick_ask &&
+    !windowManager.isQuickAskWindowDestroyed()
+  )
+    return
   cleanUpAndQuit()
 })
 
diff --git a/electron/managers/window.ts b/electron/managers/window.ts
index f24d25c61a..2faa794c98 100644
--- a/electron/managers/window.ts
+++ b/electron/managers/window.ts
@@ -45,7 +45,7 @@ class WindowManager {
     windowManager.mainWindow?.on('close', function (evt) {
       // Feature Toggle for Quick Ask
       if (!getAppConfigurations().quick_ask) return
-      
+
       if (!isAppQuitting) {
         evt.preventDefault()
         windowManager.hideMainWindow()
@@ -93,10 +93,20 @@ class WindowManager {
     this._quickAskWindowVisible = true
   }
 
+  closeQuickAskWindow(): void {
+    this._quickAskWindow?.close()
+    this._quickAskWindow?.destroy()
+    this._quickAskWindowVisible = false
+  }
+
   isQuickAskWindowVisible(): boolean {
     return this._quickAskWindowVisible
   }
 
+  isQuickAskWindowDestroyed(): boolean {
+    return this._quickAskWindow?.isDestroyed() ?? true
+  }
+
   expandQuickAskWindow(heightOffset: number): void {
     const width = quickAskWindowConfig.width!
     const height = quickAskWindowConfig.height! + heightOffset
@@ -112,8 +122,12 @@ class WindowManager {
   }
 
   cleanUp(): void {
+    this.mainWindow?.close()
     this.mainWindow?.destroy()
+    this.mainWindow = undefined
+    this._quickAskWindow?.close()
     this._quickAskWindow?.destroy()
+    this._quickAskWindow = undefined
     this._quickAskWindowVisible = false
     this._mainWindowVisible = false
   }
diff --git a/web/screens/Chat/ErrorMessage/index.tsx b/web/screens/Chat/ErrorMessage/index.tsx
index 1aea38acdb..5567956bdf 100644
--- a/web/screens/Chat/ErrorMessage/index.tsx
+++ b/web/screens/Chat/ErrorMessage/index.tsx
@@ -48,7 +48,7 @@ const ErrorMessage = ({ message }: { message: ThreadMessage }) => {
           </span>
         )
       default:
-        return message.content[0]?.text?.value
+        return <AutoLink text={message.content[0]?.text?.value} />
     }
   }
 
@@ -113,7 +113,7 @@ const ErrorMessage = ({ message }: { message: ThreadMessage }) => {
               key={message.id}
               className="mx-6 flex flex-col items-center space-y-2 text-center text-sm font-medium text-gray-500"
             >
-              <AutoLink text={getErrorTitle()} />
+              {getErrorTitle()}
               <p>
                 Jan’s in beta. Access&nbsp;
                 <span