Comment by enraged_camel

This does not match my experience. I use long-running orchestrator sessions. Each orchestrator is in charge of planning, writing kick-off prompts for implementers, answering questions from those implementers, doing code reviews and providing feedback, and answering side questions from me when I have them.

Depending on the initiative I might compact a session a dozen times, sometimes more. It is lossy, and the session certainly tends to forget earlier bits as more compactions happen, but overall it's a much better experience than starting fresh and having to re-explain everything.

The only time I compact is if the session goes wildly off-course and the context gets polluted with off-topic conversations.

Also worth noting: with Claude Code you can provide custom instructions when compacting, and instruct the LLM that is in charge of compacting the session to prioritize the retention of specific bits. It can help a lot.