I'm going to second seanmcdirmid here, a quick trick is to have Claude write a "remaining.md" if you know you have to do something that will end the session.

Example from this morning, I have to recreate the EFI disk of one of my dev vm's, it means killing the session and rebooting the vm. I had Claude write itself a remaining.md to complement the overall build_guide.vm I'm using so I can pick up where I left off. It's surprisingly effective.