How to replay a failed Stripe webhook without causing duplicate side effects

Replay is useful when a Destination was unavailable or a delivery needs to be tried after a fix. It is also a new attempt, not a time machine. Replaying an Event cannot make a partial downstream side effect disappear, and it cannot guarantee that the next attempt is safe.

Inspect before replaying

Start with the original Event identity, verification evidence, and delivery history. Identify which attempts were made, which responses were received, and whether the Destination might have processed the request before failing or timing out. If you cannot answer that question, treat replay as potentially duplicating work.

Keep original and replay history separate

A replay should append a new activity record while preserving the original delivery outcome. Changing the original attempt to look successful would make the historical record untrustworthy. A separate replay provenance record lets an operator see what happened first and what was tried later.

Webhook Handoff separates replay activity from the original delivery history. A replay can be controlled and visible, but it remains at-least-once delivery and does not remove your Destination's idempotency responsibility.

Make the repeated operation safe

• Use a stable provider Event or business key for deduplication.
• Make state transitions conditional on the expected current state.
• Record the result of a completed operation so a duplicate can reuse it.
• Do not assume an HTTP 500 means no side effect occurred.
• Confirm the Destination is healthy and configured for the intended Event.

When replay is the right tool

Replay is most useful when you have fixed a transient failure, confirmed what the original attempt did, and know the consumer can handle a repeated identity. If the failure is a deterministic code bug or the side effect is irreversible, fix the consumer and use its own reconciliation process before replaying broadly.

Further reading: Stripe's manual retry guidance and Stripe's duplicate Event guidance.