Why Your Stripe Webhooks Are Failing (And How to Fix It)

You're losing Stripe webhooks and you don't even know it. Stripe's webhook system is solid, but your receiving end isn't. Here are the 5 most common failure scenarios and exactly how to fix them. 1. Your Server Is Down During Deploys The most common cause. You deploy, your server restarts, and during that 10-30 second window, Stripe sends a webhook. Your server returns a 502. Stripe will retry, but if your deploys are frequent or your downtime is longer, you're in trouble. Stripe's retry behavior: 16 attempts over approximately 3 days, with exponential backoff. After that? The event is gone. You'd need to manually poll the Events API to recover it. Fix: Use a webhook proxy that accepts webhooks even when your server is down, then delivers them when it's back up. 2. Your Handler Times Out Stripe expects a response within 20 seconds . If your webhook handler does heavy processing (database writes, external API calls, email sends), you might exceed this. Stripe sees a timeout as a failure