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Webhooks fail every time we deploy. Fix it.
I read the webhook handler and last week's 41 failed deliveries. They all hit a 502 during a deploy. Here's the plan.
Plan modeRead 6 files
Ask for changes to the plan…
Plan · Revision 1
Retry Stripe webhooks during deploys
What will be built
A webhook that hits a 5xx mid-deploy retries with backoff instead of failing. Nothing is processed twice.
How it works
Stripe sends eventAPI returns 5xx?Retry with backoffProcessed once
1 Add a retry helper with backoff
3 Make processing idempotent
2 Wrap the webhook handler
4 Test a deploy in a preview
2 files · checked against 41 real failuresChange the planApprove and start work
Task
Retry Stripe webhooks
✓Plan approved
✓Started an agent machine
✓Added the retry helper
Wrapping the handler
Run the tests
Preview a deploy
webhook.pyretry.pytest_webhook.py
1 from app.billing.retry import with_backoff2 3 @router.post("/stripe/webhook")4 async def stripe_webhook(request: Request):5 event = await verify_signature(request)6+ result = await with_backoff(7+ lambda: process(event),8+ retry_on=(UpstreamUnavailable,),9+ attempts=5, base_delay=0.5,10+ )11+ log.info("webhook processed", id=event.id,12+ attempts=result.attempts)13 return {"ok": True}
agent machine · writing+38−42 files
Preview · agent machine · localhost:3000/billing/webhooks
Billing / Webhooks
Deliveries during deploy
Delivered
41 / 41
Recovered by retry
12
Processed twice
0
evt_3PqZ…a91invoice.paidRecovered · 2 retries
evt_3PqZ…c07customer.updatedDelivered
evt_3PqZ…e44charge.refundedRecovered · 1 retry
evt_3PqZ…f18invoice.payment_failedRecovered · 3 retries
Ready to ship
Retry Stripe webhooks
✓7 tests passed
✓Simulated a deploy in the preview
✓41 of 41 deliveries landed
Deploying to staging
✓Live on staging
Pull request #412
Waiting on your review
Review the change
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Found in a PR thread from Oct 22
"We should retry the webhook when the API is mid-deploy"
Picked upRetry the Stripe webhook on 5xx
DonePull request opened, 7 tests passing
Backlog this week
MAG-205Tests for the billing retry pathAsked you a question
MAG-201Invite expiry testsDone
MAG-190Move to the new bundlerWorking
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