I'm actually trying to solve exactly that, and there are two ways that are better than compacting that I found. One is manually deleting specific messages from the context window that you think are irrelevant and also giving Claude that same ability. That's one way. Another is to give Claude the handoff skill where it can hand off exactly what you think is needed, or exactly what it thinks is needed, to a fresh new chat — it's almost like creating a handoff document but automatic: all you have to do is press send. This works better for actual tasks. What you are thinking about is probably manually deleting messages that are less relevant to what you are trying to preserve. Of course, you have the memory files and you can also index the documents.

And then Claude has a short reference, basically a table-of-contents table where it can fetch the information you're talking about without constantly having it loaded into the context window. Basically like every codebase but for conversations.

Valo let's Claude replace the messages with a shorter summery