diff --git a/apps/vscode/webview-ui/src/components/ActionMenu.tsx b/apps/vscode/webview-ui/src/components/ActionMenu.tsx
index 01420879d4..f6ee7a2c9e 100644
--- a/apps/vscode/webview-ui/src/components/ActionMenu.tsx
+++ b/apps/vscode/webview-ui/src/components/ActionMenu.tsx
@@ -5,6 +5,7 @@ import { Button } from "@/components/ui/button";
 import { Separator } from "@/components/ui/separator";
 import { useSettingsStore } from "@/stores";
 import { bridge } from "@/services";
+import { toast } from "@/components/ui/sonner";
 import { cn } from "@/lib/utils";
 
 interface ActionMenuProps {
@@ -71,16 +72,23 @@ export function ActionMenu({ className, onAuthAction }: ActionMenuProps) {
   };
 
   const handleAuthAction = async () => {
-    if (isLoggedIn) {
-      setLoading(true);
-      try {
+    setLoading(true);
+    try {
+      if (isLoggedIn) {
         await bridge.logout();
         setIsLoggedIn(false);
-      } finally {
-        setLoading(false);
+      } else {
+        const result = await bridge.login();
+        if (result.success) {
+          setIsLoggedIn(true);
+        } else {
+          toast.error(result.error ?? "Sign-in failed. Check the logs for details.");
+        }
       }
+    } finally {
+      setLoading(false);
+      setOpen(false);
     }
-    setOpen(false);
     onAuthAction?.();
   };