Postmortem on Loop & Retry https://loopandretry.github.io/tags/postmortem/ Recent content in Postmortem on Loop & Retry Loop & Retry https://loopandretry.github.io/images/og-default.png https://loopandretry.github.io/images/og-default.png Hugo en-us Sun, 12 Jul 2026 09:00:00 -0400 Postmortem: the agent that spent $200 retrying a 400 https://loopandretry.github.io/posts/postmortem-200-dollars-retrying-a-400/ Sun, 12 Jul 2026 09:00:00 -0400 https://loopandretry.github.io/posts/postmortem-200-dollars-retrying-a-400/ An agent burned ~$200 overnight retrying an HTTP 400 — a request that was defined to fail. No component was buggy; each layer retried “reasonably.” The teardown: why retryability is a property of the error and not a default, how three nested retry caps multiply into 75 doomed attempts per item, and why per-step caps never bound a bill. With the two-line fix and a circuit breaker. Loop drift: how agents convince themselves they're making progress https://loopandretry.github.io/posts/loop-drift/ Tue, 07 Jul 2026 10:00:00 -0400 https://loopandretry.github.io/posts/loop-drift/ The worst agent failures don’t crash — they keep working. A postmortem on loop drift: an agent that stayed busy for 40 steps without getting closer to done, why the model’s own progress reports can’t catch it, and the external signals and evals that can.