I’ve been having decent luck telling it to keep track of itself in a .plan file, not foolproof, of course, but it has some ability to “preserve context” between contexts.

Right now I’m experimenting with using separate .plan files for tracking key instructions across domains like architecture and feature decisions.

> I’ve been having decent luck telling it to keep track of itself in a .plan file, not foolproof, of course, but it has some ability to “preserve context” between contexts.

This is the way. Not only have I had good luck with both a TASKS.md and TASKS-COMPLETE.md (for history), but I have an .llm/arch full of AI-assisted, for-LLM .md files (auth.md, data-access.md, etc.) that document architecture decisions made along the way. They're invaluable for effectively and efficiently crossing context chasms.

Yeah, this. Each project I work on has it's own markdown file named for the ticket or the project. Committed on the branch, and I have claude rewrite it with the "current understanding" periodically. After compacting, I have it re-read the MD file and we get started again. Quite nice.