A Guide to Long-Running Tasks with Bots (October 2026)
Good bots love long-running work. They also wander. This guide shows how to break a long job into checkpoints the bot can resume without guessing. Done, checkpoints, stop rules, and a resume brief are the whole system.
Write the finish line first
Define done in one paragraph before the bot starts: outputs, folders, and what not to touch. Put that in standing rules. Define Done Before the Bot Starts is the tip. Share that paragraph with anyone who will review the output. If done is fuzzy, the bot will invent a finish that looks busy and misses the point.
Checkpoint every slice
Ask for a short status at each milestone: what finished, what is next, and what blocked. Save status notes with clear names. Checkpoint Notes Every Slice is the habit. Use the naming convention guide so checkpoint files sort in order instead of becoming status2-final.md.
Stop rules
Tell the bot when to pause: budget hit, third failure, missing credential, or unclear requirement. Pausing is success when it protects the run. Write the stop rules next to done so the bot does not treat silence as permission to keep spending tokens.
Handoff for tomorrow
End each session with a resume brief. The next run should start from that file, not from chat memory. Write a Resume Brief is the short template: done so far, next slice, open questions, files touched.
Keep evidence with the work
For research or buying jobs, save sources and the buy brief beside the checkpoints (see the buying with bots guide). For code or site work, pair with Getting Your Bot to Do Better QA so each slice has a failing case and a checklist line.
When to kill the run
Kill it when stop rules fire twice on the same blocker, when the resume brief contradicts done, or when a human cannot say what success looks like anymore. Discuss patterns through the Links discussion for this guide.
Short checklists live under Tips. Browse Guides for related how-tos.
Timebox each slice before the bot starts it. A three-hour blob with no checkpoint is where drift hides. Smaller slices make resume briefs shorter and more honest.
When you hand a long job to a different bot mid-stream, the resume brief is the whole briefing. Do not rely on chat scrollback.
Related Tips: Define Done Before the Bot Starts, Checkpoint Notes Every Slice, Write a Resume Brief. Join the discussion through the Links discussion for this guide.
Long jobs still need a person checking in. A Guide to Managing Your Bots: Human in the Loop covers working in small batches and why you don't set it and forget it.