Ask any AI coding agent to write a Stripe webhook handler and it will produce something reasonable in thirty seconds. Ask it to verify that handler actually works and it hits a wall.
The problem isn't intelligence. It's plumbing. To debug a webhook you need to receive a real event on a public URL, check its signature, look at what actually arrived, fix your code, and run the same event again. Every step traditionally involves a human: clicking around a provider dashboard, copying a signing secret, pressing "resend event", eyeballing a request log in a browser.
An agent can do none of that. So it writes the handler, says "you should test this with a real event", and moves on. The one part of the integration that actually breaks in production is the one part the agent never touched.
What the loop should look like
The debugging loop for a webhook is mechanical: get an endpoint, trigger an event, inspect what arrived, verify the signature, fix the handler, replay the request. Every step is automatable. It just needs tools that speak exit codes and JSON instead of dashboards.
