This is a guest conversation episode of Ship It Weekly, separate from the weekly news recaps.

In this Ship It Conversations episode, I talk with Jay Lark of Hookbridge about webhook reliability, retries, idempotency, replay, security, local development, and what happens when a simple HTTP POST becomes production infrastructure.

Jay is a Principal DevOps Engineer and the founder of Hookbridge, a service focused on making webhook delivery more reliable and easier to operate.

We start with the basic model: one service sends an HTTP POST to another when something happens. The happy path is easy. The problems begin when an endpoint is unavailable, responds too slowly, receives duplicate events, or gets them out of order.

Jay explains what “at least once delivery” means and why receivers must expect duplicates.  ...