Maybe the UI could do that for sessions that the user hasn't left yet, when the deadline comes near.
You ideally want to compact before the conversation is evicted from cache. If you knew you were going to use the conversation again later after cache expiry, you might do this deliberately before leaving a session.
Anthropic could do this automatically before cache expiry, though it would be hard to get right - they'd be wasting a lot of compute compacting conversations that were never going to be resumed anyway.
This feature has been live for a few days/weeks now, and with that knowledge I try remember to a least get a process report written when I'm for example close to the quota limit and the context is reasonably large. Or continue with a /compact, but that tends to lead to be having to repeat some things that didn't get included in the summary. Context management is just hard.
I think the best option would be tell a user who is about to resurrect a conversation that has been evicted from cache that the session is not cached anymore and the user will have to face a full cost of replaying a session, not only the incremental question and answer.
(In understand under the hood that llms are n^2 by default but it's very counter intuitive - and given how popular cc is becoming outside of nerd circles, probably smaller and smaller fraction of users is aware of it)
I would like to decide on it case by case. Sometimes the session has some really deep insight I want to preserve, sometimes it's discardable.