diff --git a/packages/deploy/src/connect.test.ts b/packages/deploy/src/connect.test.ts
index 4bad3a3..8c6c5cd 100644
--- a/packages/deploy/src/connect.test.ts
+++ b/packages/deploy/src/connect.test.ts
@@ -1,6 +1,6 @@
 import test from 'node:test';
 import assert from 'node:assert/strict';
-import { relayfileIntegrationResolver } from './connect.js';
+import { connectIntegrations, relayfileIntegrationResolver } from './connect.js';
 import { createBufferedIO } from './io.js';
 
 function okJson(body: unknown, status = 200): Response {
@@ -100,3 +100,50 @@ test('relayfileIntegrationResolver connect times out clearly', async () => {
     /Timed out waiting for github OAuth/
   );
 });
+
+test('connectIntegrations fails fast on auth errors without prompting to connect', async () => {
+  const io = createBufferedIO();
+  let connectCalled = false;
+  let confirmCalled = false;
+  io.confirm = async () => {
+    confirmCalled = true;
+    return true;
+  };
+
+  const result = await connectIntegrations({
+    persona: {
+      id: 'essay',
+      intent: 'essay',
+      description: 'test persona',
+      tags: ['implementation'],
+      integrations: { notion: {} }
+    } as never,
+    workspace: 'ws-1',
+    noConnect: false,
+    io,
+    integrations: {
+      async isConnected() {
+        throw new Error(
+          'cloud integration request failed: unauthorized. Open https://origin.agentrelay.cloud/cloud to verify your cloud session, then run `agent-relay cloud whoami` and `agentworkforce login` to refresh the active workspace.'
+        );
+      },
+      async connect() {
+        connectCalled = true;
+        throw new Error('connect should not be called after auth failure');
+      }
+    }
+  });
+
+  assert.equal(confirmCalled, false);
+  assert.equal(connectCalled, false);
+  assert.deepEqual(result.outcomes, [
+    {
+      provider: 'notion',
+      status: 'failed',
+      message:
+        'cloud integration request failed: unauthorized. Open https://origin.agentrelay.cloud/cloud to verify your cloud session, then run `agent-relay cloud whoami` and `agentworkforce login` to refresh the active workspace.'
+    }
+  ]);
+  assert.ok(io.messages.some((message) => message.level === 'warn' && message.message.includes('failed to check connection status for notion')));
+  assert.ok(io.messages.some((message) => message.level === 'error' && message.message.includes('auth failed')));
+});
diff --git a/packages/deploy/src/connect.ts b/packages/deploy/src/connect.ts
index 7f4b4a5..31a1620 100644
--- a/packages/deploy/src/connect.ts
+++ b/packages/deploy/src/connect.ts
@@ -183,11 +183,13 @@ export async function connectIntegrations(input: ConnectAllInput): Promise<Conne
   const outcomes: IntegrationConnectOutcome[] = [];
 
   for (const provider of Object.keys(integrations)) {
+    let statusCheckFailure: string | undefined;
     const connected = await input.integrations
       .isConnected({ workspace: input.workspace, provider })
       .catch((err) => {
+        statusCheckFailure = err instanceof Error ? err.message : String(err);
         input.io.warn(
-          `failed to check connection status for ${provider}: ${err instanceof Error ? err.message : String(err)}`
+          `failed to check connection status for ${provider}: ${statusCheckFailure}`
         );
         return false;
       });
@@ -198,6 +200,16 @@ export async function connectIntegrations(input: ConnectAllInput): Promise<Conne
       continue;
     }
 
+    if (statusCheckFailure && isIntegrationAuthFailure(statusCheckFailure)) {
+      input.io.error(`integrations.${provider}: auth failed while checking connection status`);
+      outcomes.push({
+        provider,
+        status: 'failed',
+        message: statusCheckFailure
+      });
+      continue;
+    }
+
     if (input.noConnect) {
       input.io.error(
         `integrations.${provider}: not connected, and prompts are disabled`
@@ -285,7 +297,14 @@ async function requestJson(
     }
   });
   if (res.status === 401) {
-    throw new Error('cloud integration request failed: unauthorized. Run `agentworkforce login` and retry.');
+    throw new Error(
+      'cloud integration request failed: unauthorized. Open https://origin.agentrelay.cloud/cloud to verify your cloud session, then run `agent-relay cloud whoami` and `agentworkforce login` to refresh the active workspace.'
+    );
+  }
+  if (res.status === 403) {
+    throw new Error(
+      'cloud integration request failed: forbidden. The active account is not authorized for this workspace; open https://origin.agentrelay.cloud/cloud to verify account/workspace access, then run `agent-relay cloud whoami` and `agentworkforce login` to refresh the active workspace.'
+    );
   }
   if (!res.ok) {
     throw new Error(`cloud integration request failed: ${res.status} ${await res.text().catch(() => '')}`.trim());
@@ -293,6 +312,10 @@ async function requestJson(
   return await res.json();
 }
 
+function isIntegrationAuthFailure(message: string): boolean {
+  return /cloud integration request failed: (unauthorized|forbidden)\b/i.test(message);
+}
+
 function listHasConnectedProvider(body: unknown, provider: string): boolean {
   const candidates = Array.isArray(body)
     ? body