Design a webhook delivery system: retries, ordering, and debugging your customers can do themselves.

You control the sender; thousands of customer endpoints you've never seen control your fate. The rubric hides in three places: what 'ordering' really costs, why retries need the receiver's cooperation, and the debugging surface most designs forget.

Updated Aug 2026 · Grounded in real Forward Deployed Engineer interview loops and written to a senior-engineer editorial bar.