diff --git a/gui-js/apps/minsky-electron/src/app/managers/WindowManager.ts b/gui-js/apps/minsky-electron/src/app/managers/WindowManager.ts
index c7a1bdb89..a95f898dd 100644
--- a/gui-js/apps/minsky-electron/src/app/managers/WindowManager.ts
+++ b/gui-js/apps/minsky-electron/src/app/managers/WindowManager.ts
@@ -389,12 +389,14 @@ export class WindowManager {
     WindowManager._resolveAuthToken = resolve;
   });
 
+  const existingToken = StoreManager.store.get('authToken') || '';
+
   const loginWindow = WindowManager.createPopupWindowWithRouting({
     width: 420,
     height: 500,
     title: 'Login',
     modal: false,
-    url: '#/headless/login',
+    url: `#/headless/login?authToken=${encodeURIComponent(existingToken)}`,
   });
 
   // Resolve with null if the user closes the window before authenticating
diff --git a/gui-js/libs/core/src/lib/services/clerk/clerk.service.ts b/gui-js/libs/core/src/lib/services/clerk/clerk.service.ts
index e7544829c..e79e5d9ab 100644
--- a/gui-js/libs/core/src/lib/services/clerk/clerk.service.ts
+++ b/gui-js/libs/core/src/lib/services/clerk/clerk.service.ts
@@ -59,4 +59,18 @@ export class ClerkService {
     const token = await this.getToken();
     await this.electronService.invoke(events.SET_AUTH_TOKEN, token);
   }
+
+  async setSession(token: string): Promise<void> {
+    if (!this.clerk) throw new Error('Clerk not initialized');
+    // clerk.load() in initialize() restores the session from browser storage if still valid.
+    // If no session is active but sessions exist on the client, activate the first available one.
+    // The token parameter is a hint that the user previously authenticated.
+    if (!token) return;
+    if (!this.clerk.session && this.clerk.client?.sessions?.length > 0) {
+      await this.clerk.setActive({ session: this.clerk.client.sessions[0].id });
+    }
+    if (!this.clerk.session) {
+      throw new Error('Session expired or invalid');
+    }
+  }
 }
diff --git a/gui-js/libs/ui-components/src/lib/login/login.component.ts b/gui-js/libs/ui-components/src/lib/login/login.component.ts
index ecb275383..f9109f21e 100644
--- a/gui-js/libs/ui-components/src/lib/login/login.component.ts
+++ b/gui-js/libs/ui-components/src/lib/login/login.component.ts
@@ -1,4 +1,4 @@
-import { Component, OnInit } from '@angular/core';
+import { Component, OnInit, OnDestroy } from '@angular/core';
 import { CommonModule } from '@angular/common';
 import { FormControl, FormGroup, Validators, ReactiveFormsModule } from '@angular/forms';
 import { MatButtonModule } from '@angular/material/button';
@@ -7,6 +7,8 @@ import { MatFormFieldModule } from '@angular/material/form-field';
 import { MatProgressSpinnerModule } from '@angular/material/progress-spinner';
 import { ClerkService } from '@minsky/core';
 import { ElectronService } from '@minsky/core';
+import { ActivatedRoute } from '@angular/router';
+import { Subject, take } from 'rxjs';
 
 @Component({
   selector: 'minsky-login',
@@ -22,7 +24,7 @@ import { ElectronService } from '@minsky/core';
     MatProgressSpinnerModule,
   ],
 })
-export class LoginComponent implements OnInit {
+export class LoginComponent implements OnInit, OnDestroy {
   loginForm = new FormGroup({
     email: new FormControl('', [Validators.required, Validators.email]),
     password: new FormControl('', [Validators.required]),
@@ -32,17 +34,40 @@ export class LoginComponent implements OnInit {
   errorMessage = '';
   isAuthenticated = false;
 
-  constructor(private clerkService: ClerkService, private electronService: ElectronService) {}
+  private destroy$ = new Subject<void>();
+
+  constructor(
+    private clerkService: ClerkService,
+    private electronService: ElectronService,
+    private route: ActivatedRoute
+  ) {}
 
   async ngOnInit() {
+    this.route.queryParams.pipe(take(1)).subscribe((params) => {
+      this.initializeSession(params['authToken']);
+    });
+  }
+
+  private async initializeSession(authToken: string | undefined) {
     try {
       await this.clerkService.initialize();
+
+      if (authToken) {
+        await this.clerkService.setSession(authToken);
+      }
+
       this.isAuthenticated = await this.clerkService.isSignedIn();
     } catch (err) {
-      this.errorMessage = 'Failed to initialize authentication.';
+      this.errorMessage = 'Session expired. Please sign in again.';
+      this.isAuthenticated = false;
     }
   }
 
+  ngOnDestroy() {
+    this.destroy$.next();
+    this.destroy$.complete();
+  }
+
   get email() {
     return this.loginForm.get('email');
   }