The Webhook Failure Modes Nobody Warns You About

The Webhook Failure Modes Nobody Warns You About Until you're staring at a 78-hour Stripe retry schedule wondering why your handler never fired. Webhook integrations look simple. You point Stripe at your endpoint, you get a 200 OK, you're done. Then something breaks in production — and you have no idea what. Was it the payload? The signature? Your server? Stripe's retry queue? Something downstream? This isn't a guide to building webhook endpoints. It's a field guide to the failures developers actually hit — and how to debug them faster. Failure Mode 1: The Silent Drop Your endpoint returns 200 OK to Stripe. But your handler never fires. What actually happened: your server accepted the request, but the payload was routed to a different part of your application that silently failed. Or the event was filtered by a middleware. Or the webhook was received but the database write failed and the error was swallowed. The classic debug move: pepper your handler with console.log(). Deploy. Wait f