Ship It Conversations: Jay Lark of Hookbridge on Webhook Reliability, Retries, Idempotency, Replay, HMAC Security, Local Testing, and Operating Webhooks in Production
About this episode
In this episode, Jay Lark discusses webhook reliability and the challenges of operating webhooks in production.
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. We talk about idempotency, event IDs, retry behavior, availability during deployments, and why returning a 200 does not prove downstream processing succeeded. We also dig into observability and security. Teams need enough visibility to know whether a webhook arrived, whether signature verification passed, what response was returned, and where processing failed. Jay breaks down…
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