diff --git a/.github/workflows/main.yml b/.github/workflows/main.yml
index 4fc508e..66d3cce 100644
--- a/.github/workflows/main.yml
+++ b/.github/workflows/main.yml
@@ -38,7 +38,7 @@ env:
 jobs:
   deploy:
     runs-on: ubuntu-latest
-    timeout-minutes: 20
+    timeout-minutes: 35
     permissions:
       contents: read
       id-token: write
diff --git a/scripts/wait_for_ib_gateway_ready.sh b/scripts/wait_for_ib_gateway_ready.sh
index 49840f4..cc363f1 100644
--- a/scripts/wait_for_ib_gateway_ready.sh
+++ b/scripts/wait_for_ib_gateway_ready.sh
@@ -32,6 +32,7 @@ check_api_handshake() {
 import os
 import socket
 import struct
+import sys
 import time
 
 
@@ -51,16 +52,24 @@ except ImportError:
 if IB is not None:
     ib = IB()
     try:
-        ib.connect(host, port, clientId=client_id, timeout=timeout_seconds)
-        accounts = ib.managedAccounts()
-        if not accounts:
-            raise RuntimeError("IB API healthcheck did not receive managed accounts")
-        print(
-            "IB API ib_insync healthcheck ready: "
-            f"server_version={ib.client.serverVersion()} "
-            f"client_id={client_id} "
-            f"accounts={','.join(accounts)}"
-        )
+        try:
+            ib.connect(host, port, clientId=client_id, timeout=timeout_seconds)
+            accounts = ib.managedAccounts()
+            if not accounts:
+                raise RuntimeError("IB API healthcheck did not receive managed accounts")
+            print(
+                "IB API ib_insync healthcheck ready: "
+                f"server_version={ib.client.serverVersion()} "
+                f"client_id={client_id} "
+                f"accounts={','.join(accounts)}"
+            )
+        except Exception as exc:
+            print(
+                "IB API ib_insync healthcheck not ready: "
+                f"{type(exc).__name__}: {exc}",
+                file=sys.stderr,
+            )
+            raise SystemExit(1)
     finally:
         if ib.isConnected():
             ib.disconnect()
diff --git a/tests/test_workflow_shared_config.sh b/tests/test_workflow_shared_config.sh
index 2541498..5870859 100644
--- a/tests/test_workflow_shared_config.sh
+++ b/tests/test_workflow_shared_config.sh
@@ -8,7 +8,7 @@ grep -Fq 'GCP_PROJECT_ID: interactivebrokersquant' "$workflow_file"
 grep -Fq 'providers/github-ibkr-gateway-main' "$workflow_file"
 grep -Fq 'ibkr-gateway-deploy@interactivebrokersquant.iam.gserviceaccount.com' "$workflow_file"
 grep -Fq 'id-token: write' "$workflow_file"
-grep -Fq 'timeout-minutes: 20' "$workflow_file"
+grep -Fq 'timeout-minutes: 35' "$workflow_file"
 grep -Fq 'sync_github_secrets_to_secret_manager:' "$workflow_file"
 grep -Fq 'deploy_mode:' "$workflow_file"
 grep -Fq 'workload_identity_provider: ${{ env.GCP_WORKLOAD_IDENTITY_PROVIDER }}' "$workflow_file"