This can go both ways though. I've had instances where after a long somewhat tedious back and forth with Claude Code what I'm looking for finally "clicks" and it starts one-shotting requests left and right. But then after coming up to the end of the context window, I compact or ask it to update CLAUDE.md with what it learned and it loses the nuanced understanding it built up through trial and error and starts screwing up in the exact same ways again with fresh context.

And then I waste 20 minutes bashing my head against the wall trying to write three paragraphs meticulously documenting all the key gotchas and lessons from the "good" context window with the magic combination of words needed to get Claude back in the right head space to one-shot again.

At least if I pull that off I can usually ask Claude to use it as documentation for the project CLAUDE.md with a pretty good success rate. But man it leaves a bad taste in my mouth and makes me question whether I'm actually saving time or well into sunk cost territory...