diff --git a/app/src/services/__tests__/socketService.test.ts b/app/src/services/__tests__/socketService.test.ts
index 462356a5e..352ae0126 100644
--- a/app/src/services/__tests__/socketService.test.ts
+++ b/app/src/services/__tests__/socketService.test.ts
@@ -275,6 +275,25 @@ describe('socketService — resolveCoreSocketBaseUrl uses getCoreRpcUrl', () =>
     );
     expect(latestSocket.once).not.toHaveBeenCalledWith('queued-on-event', expect.any(Function));
   });
+
+  it('reconnects when a stale disconnected socket exists for the same token', async () => {
+    const { io } = await import('socket.io-client');
+    const ioMock = vi.mocked(io);
+    ioMock.mockClear();
+
+    hoisted.getCoreRpcUrlMock.mockResolvedValue('http://127.0.0.1:7788/rpc');
+
+    const { socketService } = await import('../socketService');
+    socketService.disconnect();
+
+    socketService.connect('mock-jwt-stale-socket');
+    await pollUntil(() => expect(ioMock).toHaveBeenCalledTimes(1));
+
+    // Same token, previous socket is disconnected=true in our mock.
+    // We should still create a fresh socket instead of returning early.
+    socketService.connect('mock-jwt-stale-socket');
+    await pollUntil(() => expect(ioMock).toHaveBeenCalledTimes(2));
+  });
 });
 
 describe('socketService — connectivity dispatch on socket events (lines 164, 212, 230, 237, 240)', () => {
diff --git a/app/src/services/socketService.ts b/app/src/services/socketService.ts
index 57cde7af1..88e72b009 100644
--- a/app/src/services/socketService.ts
+++ b/app/src/services/socketService.ts
@@ -161,6 +161,13 @@ class SocketService {
       } else if (!this.socket.disconnected) {
         // Socket is connecting, wait for it
         return;
+      } else {
+        // Stale disconnected socket instance for the same token.
+        // Drop it so this connect attempt can create a fresh socket;
+        // otherwise the async stale-invocation guard below (`|| this.socket`)
+        // returns early and leaves connectivity stuck at "connecting".
+        this.socket = null;
+        this.mcpTransport = null;
       }
     }