diff --git a/packages/deploy/src/connect.test.ts b/packages/deploy/src/connect.test.ts
index a329526..b08c31b 100644
--- a/packages/deploy/src/connect.test.ts
+++ b/packages/deploy/src/connect.test.ts
@@ -148,6 +148,79 @@ test('relayfileIntegrationResolver isConnected accepts ready runtime status as c
   );
 });
 
+test('relayfileIntegrationResolver isConnected accepts canonical OAuth-connected status before initial sync is ready', async () => {
+  const resolver = relayfileIntegrationResolver({
+    apiUrl: 'https://cloud.example.test',
+    workspaceId: 'ws-1',
+    workspaceToken: 'tok',
+    fetch: async () => okJson({
+      provider: 'slack',
+      configKey: 'slack-relay',
+      ready: false,
+      state: 'pending',
+      connectionMatched: true,
+      currentConnectionId: 'conn-slack',
+      oauth: { connected: true }
+    })
+  });
+  assert.equal(
+    await resolver.isConnected({
+      workspace: 'ws-1',
+      provider: 'slack',
+      expectedConfigKey: 'slack-relay'
+    }),
+    true
+  );
+});
+
+test('relayfileIntegrationResolver isConnected rejects OAuth status for a mismatched requested connection', async () => {
+  const resolver = relayfileIntegrationResolver({
+    apiUrl: 'https://cloud.example.test',
+    workspaceId: 'ws-1',
+    workspaceToken: 'tok',
+    fetch: async () => okJson({
+      provider: 'slack',
+      configKey: 'slack-relay',
+      ready: false,
+      state: 'pending',
+      connectionMatched: false,
+      currentConnectionId: 'conn-other',
+      oauth: { connected: true }
+    })
+  });
+  assert.equal(
+    await resolver.isConnected({
+      workspace: 'ws-1',
+      provider: 'slack',
+      expectedConfigKey: 'slack-relay'
+    }),
+    false
+  );
+});
+
+test('relayfileIntegrationResolver isConnected ignores legacy connected fields without OAuth or ready status', async () => {
+  const resolver = relayfileIntegrationResolver({
+    apiUrl: 'https://cloud.example.test',
+    workspaceId: 'ws-1',
+    workspaceToken: 'tok',
+    fetch: async () => okJson({
+      provider: 'slack',
+      configKey: 'slack-relay',
+      connectionMatched: true,
+      connected: true,
+      active: true
+    })
+  });
+  assert.equal(
+    await resolver.isConnected({
+      workspace: 'ws-1',
+      provider: 'slack',
+      expectedConfigKey: 'slack-relay'
+    }),
+    false
+  );
+});
+
 test('relayfileIntegrationResolver isConnected falls back to workspace scope for legacy default personas', async () => {
   const urls: string[] = [];
   const resolver = relayfileIntegrationResolver({
@@ -474,11 +547,65 @@ test('relayfileIntegrationResolver connect resolves when OAuth completes at work
   assert.deepEqual(opened, ['https://connect.example.test/slack']);
   assert.deepEqual(statusUrls, [
     'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?connectionId=conn-slack&scope=deployer_user',
+    'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?scope=deployer_user',
     'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?connectionId=conn-slack&scope=workspace'
   ]);
 });
 
-test('relayfileIntegrationResolver connect ignores fallback rows with a different connectionId', async () => {
+test('relayfileIntegrationResolver connect reconciles canonical status when setup-session id differs', async () => {
+  const statusUrls: string[] = [];
+  const resolver = relayfileIntegrationResolver({
+    apiUrl: 'https://cloud.example.test',
+    workspaceId: 'ws-1',
+    workspaceToken: 'tok',
+    pollIntervalMs: 0,
+    timeoutMs: 100,
+    openUrl: () => undefined,
+    sleep: async () => undefined,
+    fetch: async (input, init) => {
+      const url = input.toString();
+      if (url.endsWith('/integrations/connect-session')) {
+        assert.equal(init?.method, 'POST');
+        return okJson({
+          sessionUrl: 'https://connect.example.test/slack',
+          connectionId: 'setup-session-id'
+        });
+      }
+      statusUrls.push(url);
+      if (url.includes('connectionId=setup-session-id')) {
+        return okJson({
+          provider: 'slack',
+          configKey: 'slack-relay',
+          ready: false,
+          state: 'pending',
+          connectionMatched: false,
+          currentConnectionId: 'conn-slack-final',
+          oauth: { connected: true }
+        });
+      }
+      return okJson({
+        provider: 'slack',
+        configKey: 'slack-relay',
+        ready: false,
+        state: 'pending',
+        connectionMatched: true,
+        currentConnectionId: 'conn-slack-final',
+        oauth: { connected: true }
+      });
+    }
+  });
+
+  assert.deepEqual(
+    await resolver.connect({ workspace: 'ws-runtime', provider: 'slack' }),
+    { connectionId: 'conn-slack-final' }
+  );
+  assert.deepEqual(statusUrls, [
+    'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?connectionId=setup-session-id&scope=deployer_user',
+    'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?scope=deployer_user'
+  ]);
+});
+
+test('relayfileIntegrationResolver connect rejects canonical status with a different configKey', async () => {
   const resolver = relayfileIntegrationResolver({
     apiUrl: 'https://cloud.example.test',
     workspaceId: 'ws-1',
@@ -487,6 +614,49 @@ test('relayfileIntegrationResolver connect ignores fallback rows with a differen
     timeoutMs: 1,
     openUrl: () => undefined,
     sleep: async () => undefined,
+    fetch: async (input) => {
+      const url = input.toString();
+      if (url.endsWith('/integrations/connect-session')) {
+        return okJson({
+          sessionUrl: 'https://connect.example.test/slack',
+          connectionId: 'setup-session-id',
+          configKey: 'slack-relay'
+        });
+      }
+      if (url.includes('connectionId=setup-session-id')) {
+        return okJson({
+          provider: 'slack',
+          configKey: 'slack-relay',
+          connectionMatched: false,
+          oauth: { connected: true }
+        });
+      }
+      return okJson({
+        provider: 'slack',
+        configKey: 'slack-ricky',
+        connectionMatched: true,
+        currentConnectionId: 'conn-slack-ricky',
+        oauth: { connected: true }
+      });
+    }
+  });
+
+  await assert.rejects(
+    resolver.connect({ workspace: 'ws-runtime', provider: 'slack' }),
+    /Timed out waiting for slack OAuth/
+  );
+});
+
+test('relayfileIntegrationResolver connect reconciles canonical fallback rows with a different connectionId', async () => {
+  const statusUrls: string[] = [];
+  const resolver = relayfileIntegrationResolver({
+    apiUrl: 'https://cloud.example.test',
+    workspaceId: 'ws-1',
+    workspaceToken: 'tok',
+    pollIntervalMs: 0,
+    timeoutMs: 100,
+    openUrl: () => undefined,
+    sleep: async () => undefined,
     fetch: async (input, init) => {
       const url = input.toString();
       if (url.endsWith('/integrations/connect-session')) {
@@ -496,6 +666,7 @@ test('relayfileIntegrationResolver connect ignores fallback rows with a differen
           connectionId: 'conn-slack-new'
         });
       }
+      statusUrls.push(url);
       if (url.includes('scope=deployer_user')) {
         return okJson({ provider: 'slack', status: 'pending' });
       }
@@ -507,14 +678,20 @@ test('relayfileIntegrationResolver connect ignores fallback rows with a differen
     }
   });
 
-  await assert.rejects(
-    resolver.connect({
+  assert.deepEqual(
+    await resolver.connect({
       workspace: 'ws-runtime',
       provider: 'slack',
       allowWorkspaceFallback: true
     }),
-    /Timed out waiting for slack OAuth/
+    { connectionId: 'conn-slack-other' }
   );
+  assert.deepEqual(statusUrls, [
+    'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?connectionId=conn-slack-new&scope=deployer_user',
+    'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?scope=deployer_user',
+    'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?connectionId=conn-slack-new&scope=workspace',
+    'https://cloud.example.test/api/v1/workspaces/ws-runtime/integrations/slack/status?scope=workspace'
+  ]);
 });
 test('relayfileIntegrationResolver connect sends scope=workspace and scopes status polls (workspace source)', async () => {
   const bodies: unknown[] = [];
diff --git a/packages/deploy/src/connect.ts b/packages/deploy/src/connect.ts
index c65921f..e9ec130 100644
--- a/packages/deploy/src/connect.ts
+++ b/packages/deploy/src/connect.ts
@@ -242,15 +242,18 @@ const fallbackSource = workspaceFallbackSource(
       while (Date.now() < deadline) {
         await sleepImpl(opts.pollIntervalMs ?? 2_000);
         const pollToken = await resolveWorkspaceToken(opts.workspaceToken);
-        const status = await fetchIntegrationStatusForScope({
+        const statusArgs = {
           fetchImpl,
           apiUrl,
           token: pollToken,
           workspaceId,
           provider,
           source: effectiveSource,
-          ...(sessionId ? { connectionId: sessionId } : {}),
           io
+        };
+        const status = await fetchIntegrationStatusForScope({
+          ...statusArgs,
+          ...(sessionId ? { connectionId: sessionId } : {})
         });
         if (statusIsConnectedForSource(status, provider, effectiveSource)) {
           const connectionId = readConnectionId(status)
@@ -260,7 +263,23 @@ const fallbackSource = workspaceFallbackSource(
           return { connectionId };
         }
 
-const fallbackSource = workspaceFallbackSource(
+        if (sessionId) {
+          const canonicalStatus = await fetchIntegrationStatusForScope(statusArgs);
+          if (statusIsConnectedForSource(
+            canonicalStatus,
+            provider,
+            effectiveSource,
+            sessionConfigKey
+          )) {
+            const connectionId = readConnectionId(canonicalStatus)
+              ?? sessionId
+              ?? provider;
+            io?.info(`${provider} connected.`);
+            return { connectionId };
+          }
+        }
+
+        const fallbackSource = workspaceFallbackSource(
           effectiveSource,
           allowWorkspaceFallback === true
         );
@@ -290,6 +309,31 @@ const fallbackSource = workspaceFallbackSource(
             io?.info(`${provider} connected.`);
             return { connectionId };
           }
+          if (sessionId) {
+            const canonicalFallbackStatus = await fetchIntegrationStatusForScope({
+              fetchImpl,
+              apiUrl,
+              token: pollToken,
+              workspaceId,
+              provider,
+              source: fallbackSource,
+              io
+            });
+            if (
+              statusIsConnectedForSource(
+                canonicalFallbackStatus,
+                provider,
+                fallbackSource,
+                sessionConfigKey
+              )
+            ) {
+              const connectionId = readConnectionId(canonicalFallbackStatus)
+                ?? sessionId
+                ?? provider;
+              io?.info(`${provider} connected.`);
+              return { connectionId };
+            }
+          }
         }
       }
 
@@ -966,25 +1010,29 @@ function statusMatchesExpectedConfigKey(value: unknown, expectedConfigKey?: stri
 }
 
 /**
- * A provider counts as connected for deploy only when the cloud's
- * runtime-visible status is ready. Pending/syncing rows mean the sandbox will
- * not see a ready mounted provider yet, so deploy must prompt/reconnect
- * instead of shipping a silently-dead proactive agent.
+ * A provider counts as connected for deploy when the cloud confirms the
+ * canonical credential row/backend connection exists. Top-level `ready` still
+ * means initial sync/writeback are healthy, but OAuth completion can precede
+ * that readiness and should not force deploy back through OAuth.
  *
- *   - `ready`     — sync complete, writeback healthy. Fully usable.
- *   - `pending`   — OAuth row exists but runtime-visible sync is not ready.
- *   - `syncing`   — initial sync is still running.
- *   - `degraded`  — sync/writeback is unhealthy enough not to trust deploy.
- *   - `error`     — sync failed or writeback errored. Treat as not-connected
- *                   so the user re-runs OAuth (or fixes the upstream cause).
- *
- * Legacy fields (`connected`, `active`, `state`, `ready: true`, `oauth.connected`)
- * are intentionally narrowed here; deploy is checking runtime readiness, not
- * merely OAuth existence.
+ * When the status route is asked about a specific setup-session id, it returns
+ * `connectionMatched:false` for a different final connection. Treat that as
+ * not connected for the exact poll; the caller also performs a canonical
+ * no-connectionId poll to reconcile successful OAuth completion.
  */
 function isConnectedStatus(value: unknown): boolean {
   if (!value || typeof value !== 'object' || Array.isArray(value)) return false;
   const record = value as Record<string, unknown>;
+  if (record.connectionMatched === false) {
+    return false;
+  }
+  const oauth = record.oauth;
+  if (oauth && typeof oauth === 'object' && !Array.isArray(oauth)) {
+    const oauthRecord = oauth as Record<string, unknown>;
+    if (oauthRecord.connected === true) {
+      return true;
+    }
+  }
   return record.status === 'ready'
     || record.state === 'ready'
     || record.ready === true;