alt Hacker NewsI think the answer for both cases is supposed to be finishing a "good" session with "based on what you've learned about this project, please update the CLAUDE.md/AGENTS.md/README.md files."
Ideally that replaces the back and forth cycle of it's this, no it's that, it's that for reasons XYZ with a single ingestible blob that gets the agent up to speed.
I've actually had mixed results with that without some manual curation - sometimes by the time a session has gone on for a while (heaven forbid it go through multiple compactions), the agent has so much extraneous/incorrect context for docs that it can't write documentation effectively.
Sometimes it's better to dump context incrementally, reinitialize the agent with a subset of the context, or manually prime it, then ask it to write documentation as a focused task.