Fix Stripe Payments, Subscriptions & Webhook Failures

Webhooks are where payment bugs live

Almost every serious payment problem traces back to webhook handling, because that is the only place where the payment provider's view of the world and your database can disagree.

The dangerous property is that they fail quietly. Money moves correctly, the customer is charged, and your system simply never learns about it — so the failure surfaces days later as a support complaint rather than as an error.

The rules that make webhooks reliable

Four properties, and implementations missing any of them will eventually drift.

• Verify the signature on every event, without exception.
• Handle repeats safely: the same event will arrive more than once, and processing it twice must change nothing.
• Reply quickly and do the work afterwards, or the provider will time out and retry.
• Treat the payment provider as the source of truth and reconcile against it, rather than assuming your database is correct.

Test the unhappy paths

Checkout is the path everyone tests, and it is the one that rarely breaks. The failures happen in the states nobody exercised: a card expiring mid-subscription, a refund, a plan change halfway through a period, a dispute, a retry after a failed renewal.

Stripe's test clocks make all of these reproducible without waiting a month. An integration that has not been through them is not finished, whatever the checkout page looks like.

Reconciliation is the safety net

Even a correct integration drifts occasionally — a webhook lost during an outage, a manual refund issued from the dashboard. A scheduled job that compares your records against the provider's and reports differences catches these before customers do.

It is a small amount of work and it is the difference between finding out from a report and finding out from an angry email.