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02 MAY 2026

David's problem: Calendar agents failing silently for multiple new signups

David traced a pattern of calendar agents failing for new users across multiple courses and directed an investigation into each agent turn to find the root cause.


After reviewing bootstrap results for new signups, David found calendar agents consistently failing.

calendar is failed on 5 and running on 2... go find out why the calendar agents are failing. go through each turn of the calendar agents to see, at the lowest level, exactly whats happening, what tools are being called etc and trace where the errors are

The investigation found calendar agents were hitting context window limits when fed massive topicId lists (17+ topics + attachments + announcements for a single course). David then asked whether the solution was smaller batches rather than shorter prompts, which led to a plan for splitting large calendar delegation into multiple agent calls.


kerracalendar-agentbootstrapcontext-windowdebugcodex