Stripe Webhooks Not Working
Stripe webhooks stop working in 2026 for five main reasons: your endpoint URL changed after deployment (DNS or path update broke the registered URL), your server is returning non-2xx responses (Stripe marks delivery as failed), webhook signature verification is rejecting valid events (wrong secret, double-decoding the body), the endpoint is not subscribed to the right event types, or you are testing in production with sandbox events (or vice versa).
Why This Happens
- Configuration gaps between tools or services
- Missing integrations or manual workarounds that weren't designed to scale
- Changes in vendor behavior, pricing, or API that weren't communicated clearly
What To Check First
- Verify your current setup matches the vendor's latest documentation
- Look for recent changes — platform updates, new team members, configuration drift
- Check if the problem is consistent or intermittent (different root causes, different fixes)
When To Escalate
- The problem is costing you money or customers per week
- You've spent more than 2 hours on it without progress
- A vendor quoted you more than $500 and you're not sure if it's necessary
Dealing with this right now?
The fastest debug path: go to Stripe Dashboard → Developers → Webhooks → [your endpoint] → Recent deliveries. Find a failed delivery and read the response your server returned. A 500 means your handler is crashing — add error logging around the webhook processing code. A 401 or 403 means your server is blocking the request — check if you have authentication middleware that runs before the webhook handler. A timeout means your handler takes more than 30 seconds — move processing to a background queue and return 200 immediately.
