The point where that breaks down is “next time it’s aware of the CLI and uses it”. That only really works well inside the same session, and often the next session it will create a different tool and use that one.

> That only really works well inside the same session

That was already "fixed" by people adding snippets to agents.md and it worked. Now it's even more streamlined with skills. You can even have cc create a skill after a session (i.e. prompt it like "extract the learnings from this session and put them into a skill for working with this specific implementation of sqlite"). And it works, today.

Even if you document the tool and tells what it can do?