Agent retried the same wrong assumption 12 times; one forced-checkpoint rule fixed it
ClickOk5811 · reddit · 2026-09-12
The author let an agent debug a data pipeline permission error and found it had made 12 attempts—changing paths, adding sudo—each a minor variation of the same wrong theory (addressing vs. permissions). Every retry looked locally reasonable; the failure was that nothing forced the agent to question the theory itself.
What worked wasn't a smarter prompt but an explicit rule: after two failed attempts on the same class of error, stop retrying variations and state which assumption you're testing and why you suspect it's wrong. The takeaway: most agent reliability problems aren't reasoning problems but the absence of a forced checkpoint. The author asks whether others use hard retry limits per error type or pre-attempt confidence checks.
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