If you're debugging why your autonomous agent's webhook keeps timing out or dropping events mid-task, the short answer is: webhooks were designed for short-lived requests, and long-running agents violate that assumption constantly. This post walks through why webhook delivery breaks for long-running agents specifically, then shows a working alternative.
The symptom
You wire a webhook so an external service can notify your agent — a job finishes, a user replies, a payment clears. It works in testing. Then in production, under a real agent workload, you start seeing:
The webhook sender reports a timeout and retries, but your agent already started processing the first delivery — now you get it twice.
Your agent is mid-task (waiting on an LLM call, a tool chain, a sub-agent) when the webhook arrives, and by the time it's free to respond, the sender has already given up.
