Spent 11 hours last week chasing a webhook retry loop that turned out to be one wrong status code

Tessa Foster · 2026-10-25T00:10:02.992896+00:00

Our billing sync started double-charging a small handful of accounts, maybe 6 out of 400, and I figured it was a race condition in our job queue. I went down that path for most of Tuesday and Wednesday, added logging everywhere, even rebuilt part of the queue config. Turned out a downstream API was returning 200 on a partial failure, so our retry logic kept firing because it never saw an error. One line fix. The logging I added is still running in prod and honestly I might keep it. Has anyone else gotten burned by a vendor sending a 200 when they really meant 500?

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Spent 11 hours last week chasing a webhook retry loop that turned out to be one wrong status code | B2b Saas Ops - Free To Speak