diff --git a/apps/macos/Sources/Clawdis/ConnectionsSettings.swift b/apps/macos/Sources/Clawdis/ConnectionsSettings.swift
index 85a0acb6e8..d992546189 100644
--- a/apps/macos/Sources/Clawdis/ConnectionsSettings.swift
+++ b/apps/macos/Sources/Clawdis/ConnectionsSettings.swift
@@ -84,12 +84,6 @@ struct ConnectionsSettings: View {
                     .buttonStyle(.bordered)
                     .disabled(self.store.whatsappBusy)
 
-                    Button("Wait for scan") {
-                        Task { await self.store.waitWhatsAppLogin() }
-                    }
-                    .buttonStyle(.bordered)
-                    .disabled(self.store.whatsappBusy)
-
                     Spacer()
 
                     Button("Logout") {
diff --git a/apps/macos/Sources/Clawdis/ConnectionsStore.swift b/apps/macos/Sources/Clawdis/ConnectionsStore.swift
index 59f98b77f4..e57b981838 100644
--- a/apps/macos/Sources/Clawdis/ConnectionsStore.swift
+++ b/apps/macos/Sources/Clawdis/ConnectionsStore.swift
@@ -158,10 +158,11 @@ final class ConnectionsStore {
         }
     }
 
-    func startWhatsAppLogin(force: Bool) async {
+    func startWhatsAppLogin(force: Bool, autoWait: Bool = true) async {
         guard !self.whatsappBusy else { return }
         self.whatsappBusy = true
         defer { self.whatsappBusy = false }
+        var shouldAutoWait = false
         do {
             let params: [String: AnyCodable] = [
                 "force": AnyCodable(force),
@@ -174,12 +175,16 @@ final class ConnectionsStore {
             self.whatsappLoginMessage = result.message
             self.whatsappLoginQrDataUrl = result.qrDataUrl
             self.whatsappLoginConnected = nil
+            shouldAutoWait = autoWait && result.qrDataUrl != nil
         } catch {
             self.whatsappLoginMessage = error.localizedDescription
             self.whatsappLoginQrDataUrl = nil
             self.whatsappLoginConnected = nil
         }
         await self.refresh(probe: true)
+        if shouldAutoWait {
+            Task { await self.waitWhatsAppLogin() }
+        }
     }
 
     func waitWhatsAppLogin(timeoutMs: Int = 120_000) async {
diff --git a/src/web/login-qr.ts b/src/web/login-qr.ts
index 486b2deb6d..f12466d57c 100644
--- a/src/web/login-qr.ts
+++ b/src/web/login-qr.ts
@@ -1,5 +1,7 @@
 import { randomUUID } from "node:crypto";
 
+import { DisconnectReason } from "@whiskeysockets/baileys";
+
 import { danger, info, success } from "../globals.js";
 import { logInfo } from "../logger.js";
 import { defaultRuntime, type RuntimeEnv } from "../runtime.js";
@@ -7,6 +9,8 @@ import { renderQrPngBase64 } from "./qr-image.js";
 import {
   createWaSocket,
   formatError,
+  getStatusCode,
+  logoutWeb,
   readWebSelfId,
   waitForWaConnection,
   webAuthExists,
@@ -22,6 +26,7 @@ type ActiveLogin = {
   qrDataUrl?: string;
   connected: boolean;
   error?: string;
+  errorStatus?: number;
   waitPromise: Promise<void>;
 };
 
@@ -127,6 +132,7 @@ export async function startWebLoginWithQr(
     .catch((err) => {
       if (activeLogin?.id === login.id) {
         activeLogin.error = formatError(err);
+        activeLogin.errorStatus = getStatusCode(err);
       }
     });
 
@@ -186,6 +192,14 @@ export async function waitForWebLogin(
   }
 
   if (login.error) {
+    if (login.errorStatus === DisconnectReason.loggedOut) {
+      await logoutWeb(runtime);
+      const message =
+        "WhatsApp reported the session is logged out. Cleared cached web session; please scan a new QR.";
+      await resetActiveLogin(message);
+      runtime.log(danger(message));
+      return { connected: false, message };
+    }
     const message = `WhatsApp login failed: ${login.error}`;
     await resetActiveLogin(message);
     runtime.log(danger(message));