So you either need to be very explicit about starting a NEW plan if you want to do more than one plan in a session, or close and start a new session between plans.
Hopefully this new feature will get less buggy. Previously the plan was only in context and not written to disk.
For example making a computer use agent… Made the plan, implementation was good, now I want to add a new tool for the agent, but I want to discuss best way to implement this tool first.
Clearing context means Claude forgets everything about what was just built.
Asking to discuss this new tool in plan mode makes Claude rewrite entire spec for some reason.
As workaround, I tell Claude “looks good, delete the plan” before doing anything. I liked the old way where once you exit plan mode the plan is done, and next plan mode is new plan with existing context.
Now it has a file it can refer to (call it "memory" to be fancy) without having to keep everything in context. The plan in the file survives over autocompact a lot better and it can just copy it to the project directory without rewriting it from memory.