I spent a weekend building a webhook debugger and lost sleep over a silent Stripe failure

Here is the thing nobody tells you about Stripe webhooks: they look simple until they are not. It was a Friday night. I had just shipped a new feature. Everything worked in development. In production? Silent failure. The payment succeeded, but my database never updated. No error. No warning. Just... nothing. Three hours of debugging later, I found the problem: my webhook handler was crashing on a malformed payload edge case, Stripe was retrying silently, and by the time I checked, the original event had long expired from the retry queue. Sound familiar? It turns out this is the most common webhook problem developers face. What I Built I stopped that night and built Hooklog — a webhook proxy that gives you full visibility into what is actually hitting your endpoints. With Hooklog: Live payload inspection — see every webhook as it arrives, headers and body Failure alerting — get emailed the moment a webhook returns 4xx or 5xx Replay — re-send any captured webhook to debug your fix No sig