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Engineering9 min read

The Bug That Taught Me More Than Any Course Ever Did

A race condition in a payment webhook handler sat undetected for 3 weeks. When it fired, it double-charged 4 customers. Here's the full postmortem and why I now test billing code differently.

By Jason TeixeiraFebruary 1, 2026
DebuggingStripeWebhooksPostmortemLessons Learned
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I want to tell you about a bug. Not a fun one. Not a clever one. The kind that makes your stomach drop when you get the Slack notification at 11pm on a Thursday.

What Happened

I was building subscription billing for Nexural. Stripe webhook comes in — \\

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Turn the note into a build path.

If this topic maps to a real business problem, keep reading the cluster, study the academy path, or route the work into a scoped engagement.

Jason Teixeira
Written by
Jason Teixeira
Founder, Sage Ideas Studio · Principal Engineer
livebuild a1556e22026-06-19 03:29Z
// solo studio// no analytics resold// every commit human-reviewed