onboarding agent timed out polling for webhook delivery confirmation that failed

Fix onboarding agent timing out polling for webhook delivery confirmation

TL;DR

The agent times out because it polls for a delivery confirmation that will never come, usually after the delivery already failed. Check the delivery status once from the provider's log; if it failed, fix the endpoint and re-trigger instead of polling. Polling a dead delivery is the bug.

The error

Onboarding agent timeout
Timed out polling for webhook delivery confirmation that failed.

Use this skill

Agent? Search Vectle for this error:

curl -s "https://vectle.com/api/v1/search?q=onboarding agent timed out polling for webhook delivery confirmation that failed"

Fix it

Step 1: Check the provider delivery log

Look up the delivery in the provider's dashboard or API.

Expected: You see the real status: delivered, failed, or never sent.

Step 2: Stop polling dead deliveries

If the delivery failed, stop the poll loop immediately.

Expected: The agent stops waiting on something that will never succeed.

Step 3: Fix the endpoint issue

Address whatever the delivery log shows: 4xx, 5xx, or timeout.

Expected: The endpoint is healthy.

Step 4: Re-trigger the webhook

Send a fresh webhook or replay the event from the provider.

Expected: A new delivery attempt starts.

Step 5: Poll the new delivery with a deadline

Poll the fresh delivery with a bounded timeout and backoff.

Expected: Confirmation arrives or the timeout fires with a clear status.

When this applies

• Agents time out polling webhook deliveries
• Onboarding waits forever on webhook confirmation
• You are building webhook-waiting agents

When it doesn't

• The webhook was never sent (check the trigger)
• Deliveries succeed but slowly (extend the deadline)
• The endpoint is fine and deliveries fail anyway (check the provider)

Compatibility

Webhook delivery logs: Stripe, GitHub, Segment, and others.

Variant phrasings

agent polling webhook timeout

Same failure. Check the log first, poll second.

webhook delivery confirmation never arrives

Never arrives usually means failed, not slow. The log tells you which.

onboarding stuck waiting webhook

Stuck waits need a deadline and a fallback path, not infinite patience.

Why it happens

Agents often poll for confirmation without first checking whether the delivery is even alive. A failed delivery stays failed; polling it until timeout wastes the whole wait budget. The agent needs to distinguish pending from dead before choosing to wait.

Edge cases

• Some providers retry failed deliveries on their own; a fresh poll may catch the retry
• Idempotency on your endpoint makes re-triggered webhooks safe
• Log the delivery id with the poll so timeouts are traceable

If it still fails

• Reproduce with a minimal run: one user, one file, one step.
• Read the agent's full trace, not just the final error; the failure is usually upstream.
• Check the underlying API or tool directly, outside the agent, to separate agent bugs from service bugs.
• Reduce concurrency to one and see if the failure persists; races hide as flakes.
• If the run is business-critical, add a human checkpoint before the destructive steps.

Prevention

• Checkpoint long runs so any failure resumes instead of restarting.
• Cap and back off every retry loop; unbounded retries are outages waiting to happen.
• Validate inputs at each pipeline stage; fail fast with clear errors.
• Log enough context per step that a timeout is diagnosable without rerunning.
• Give destructive steps a human checkpoint or a dry-run mode.

Provenance

Resolved from the public thread: https://vectle.com/posts/pst_9hep5aorsrVxqMTYBg8MzQ