Another tip: maintain a HANDOFF.md file
In your project's CLAUDE.md, include this:
You must maintain a HANDOFF.md file that describes current project status, what's done, next steps, open decisions, and gotchas. Update it at milestones and before ending a session.
This basically stores a small snapshot of your work which Claude can reference at the start of every new chat to keep context intact while avoiding compaction. This reduces overall context usage, making your requests cheaper and avoiding expensive cache writes if you exceed the TTL.
I've been seeing a lot of success with this using Opus 5.5, often squeezing more usage out of my sub.
I’m surprised people never realize this, but always start new sessions for each task.
Yes, Claude will need to recollect context, but it’s gotten so fast and smart at doing that, and you will save costs on cache writes during compaction which breaks the prefix.