Why Your API Webhook Delivery Guarantees Are a Lie episode artwork

EPISODE · Jun 2, 2026 · 10 MIN

Why Your API Webhook Delivery Guarantees Are a Lie

from The Developer Tools Podcast with Fexingo: APIs, Infrastructure, and Software for Engineers · host Fexingo

Lucas and Luna unpack the uncomfortable truth behind API webhook delivery guarantees. Most developers assume at-least-once delivery means reliability, but the real failure mode is silent duplication. Using Stripe's idempotency keys and GitHub's webhook retry logic as case studies, they dissect why exactly-once delivery is mathematically impossible over a network, and how to build idempotent receivers that survive replay attacks, network partitions, and lazy engineering. Specifics include: how Stripe's 2-second timeout window works, why GitHub's 'redeliver' button is a footgun, and the one logging pattern that catches double charges before customers do. For engineers building payment integrations, event-driven architectures, or any system where webhooks carry business-critical payloads. #Webhooks #API #Idempotency #EventDrivenArchitecture #Stripe #GitHub #RetryStrategy #ExactlyOnce #AtLeastOnce #NetworkReliability #APIDesign #SoftwareEngineering #DevTools #DeveloperExperience #Backend #FexingoBusiness #BusinessPodcast #TechPodcast Keep every episode free: buymeacoffee.com/fexingo

Lucas and Luna unpack the uncomfortable truth behind API webhook delivery guarantees. Most developers assume at-least-once delivery means reliability, but the real failure mode is silent duplication. Using Stripe's idempotency keys and GitHub's webhook retry logic as case studies, they dissect why exactly-once delivery is mathematically impossible over a network, and how to build idempotent receivers that survive replay attacks, network partitions, and lazy engineering. Specifics include: how Stripe's 2-second timeout window works, why GitHub's 'redeliver' button is a footgun, and the one logging pattern that catches double charges before customers do. For engineers building payment integrations, event-driven architectures, or any system where webhooks carry business-critical payloads. #Webhooks #API #Idempotency #EventDrivenArchitecture #Stripe #GitHub #RetryStrategy #ExactlyOnce #AtLeastOnce #NetworkReliability #APIDesign #SoftwareEngineering #DevTools #DeveloperExperience #Backend #FexingoBusiness #BusinessPodcast #TechPodcast Keep every episode free: buymeacoffee.com/fexingo

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Why Your API Webhook Delivery Guarantees Are a Lie

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This episode is 10 minutes long.

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This episode was published on June 2, 2026.

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Lucas and Luna unpack the uncomfortable truth behind API webhook delivery guarantees. Most developers assume at-least-once delivery means reliability, but the real failure mode is silent duplication. Using Stripe's idempotency keys and GitHub's...

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