SERIES

Building with AI task windows

Running real work through Cowork and Claude task windows: the runtime modes, the failures, and the protocols that make them reliable.

  1. 1Five hours to figure out the JSONL was always on diskI opened the RAG Factory task window with a one-line ask. Six task windows, delta RAG each, remind me which skill to trigger. What followed was five hours of trust breaking down between me, the skill I built, and the task windows themselves. I want to walk through what happened, because the failure mode is not a bug in any single piece. It is the assumptions each piece carries about the others. If you run Cowork task windows for anything more than throwaway chats, you are going to hit this. Here is what I got wrong, what I finally got right, and the protocol I now use to make sure the next delta RAG takes minutes instead of hours.Free