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area: agentClaude agent loopClaude agent loopenhancementNew feature or requestNew feature or requestpriority: highBlocks users or degrades experienceBlocks users or degrades experiencesize: mediumA few files, clear scopeA few files, clear scope
Description
Context
Chief currently uses a global max iterations counter (NUMBER_OF_TASKS + 5) to limit the total number of agent loop cycles.
Problem
- Exhausting iterations stops Chief entirely — when max iterations is reached, Chief stops instead of flagging the stuck task for human review and moving on to other unblocked tasks
- Max iterations is the wrong abstraction — completing 10 tasks successfully is not the same as completing 1 task and failing 9 times. A user with 290 tasks hits the limit after ~10 tasks
- Existing bug: max iterations is calculated from the task count of the first PRD in the list, not the currently selected one
Suggested solution
- Track retry count per task, not globally
- When a task fails repeatedly (e.g. 3 times), mark it as needing human review and move on to other unblocked tasks
- Consider whether failed tasks could be unblocked by completing other tasks or refactoring tasks first
- Fix the bug where iteration count uses the wrong PRD's task count
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area: agentClaude agent loopClaude agent loopenhancementNew feature or requestNew feature or requestpriority: highBlocks users or degrades experienceBlocks users or degrades experiencesize: mediumA few files, clear scopeA few files, clear scope