What’s the Most Painful Webhook Bug You’ve Faced?

I want to ask the Dev.to community something real.

We all know webhooks are powerful — they connect Stripe payments, GitHub events, Shopify orders, Razorpay transactions. But they also break in the most frustrating ways.

For me, the worst was when Stripe kept throwing ‘Invalid Signature’ errors. Hours wasted, only to realize Express body‑parser was silently altering the raw payload.

Other times, retries created duplicate database entries or events arrived out of order, breaking my logic.

I’m curious: What’s the most painful webhook bug you’ve faced?

Signature mismatches?

Retries & duplicates?

Payload parsing errors?

Provider changes that broke your handler overnight?

I’m building Hookmetry, a free webhook tester and debugging tool, to make these problems easier to solve. You can generate endpoints instantly, inspect payloads, replay requests, and catch issues faster.

But more importantly — I want to learn from your stories. Drop your worst webhook debugging nightmare in the comments.

Let’s turn this into a community thread of real fixes and lessons learned.