Stop-condition recipe · 2026-10-11
Three strikes, then stop: a retry-limit recipe
How to stop an agent from looping on a failing task and burning time and budget.
The most common agent failure isn't a dramatic mistake. It's a loop. The task fails, the agent tries again with a small change, fails again, and keeps going. Each attempt costs tokens, time and sometimes money. By morning you have forty versions of the same broken thing.
The fix is a hard retry limit with a clean handoff.
The recipe
RETRY LIMIT
- Any single task gets at most 3 attempts.
- Before attempt 2 and 3, write one line: what failed and what
you will change. If you can't name a change, stop now.
- After the 3rd failure, stop the task. Do not start a related
task as a workaround.
- Write a handoff note: the goal, the 3 attempts, the exact error
or check that failed, and your best guess at the cause.
- Mark the task "needs owner" and move to the next item in the
queue.Why three
One retry catches flukes: a timeout, a rate limit, a flaky network. A second retry catches a real fix. After three, the agent is guessing. Guessing is your job, not its job.
The two lines that matter most
"If you can't name a change, stop now." Retrying the same thing and hoping is the loop. Making the agent state the change first kills most loops at attempt two.
"Do not start a related task as a workaround." A blocked agent will find another path to the same goal, like a different tool, a different account or a quieter method. That's exactly the behaviour you don't want. Blocked means stop and tell me.
What the handoff note buys you
When you sit down, you don't need to reconstruct what happened. You read four lines, see the failing check, and either fix the input or change the rule. Most fixes take a minute when the note is good.
I run this on my own content writers. When a draft fails its checks three times, it parks and tells me which check it failed. Usually the check is right and the brief was wrong.
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