The Undocumented Webhook Failures Haunting Production

Webhook integrations often fail silently in production without obvious error signals, and the standard retry cycles (up to 78 hours) make debugging painfully slow. This field guide maps the specific failure patterns developers actually encounter—from silent drops to signature validation loops—with practical debugging strategies that reduce mean-time-to-resolution. For any application handling critical integrations like Stripe payments, understanding these failure modes is essential to preventing transaction losses and data inconsistencies.