How to Fix Stripe Webhook Signature Failures When Replaying Dead-Letter Queue Events
Stripe webhook signature verification includes a 300-second replay protection window, which causes legitimate dead-letter queue replays to fail if the event is held longer than five minutes. The SDK checks both cryptographic authenticity and timestamp freshness, making delayed replays indistinguishable from malicious replay attacks. Common workarounds — such as skipping verification on retried events or extending the tolerance window to 72 hours — introduce serious security vulnerabilities that can be exploited to forge billing events. The recommended fix is a two-stage architecture that separates ingress verification from internal delivery: an ingress proxy verifies the original Stripe signature immediately and stores the payload durably, then re-signs it with a fresh timestamp before forwarding to downstream handlers. This approach preserves full replay protection while allowing delayed retries to pass standard signature verification without any code changes in the application layer.
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