I was under the impression a compact resurrected the session anyway so it is not a good idea on a cold session. Is that true or is it actually cheaper?

Yes, it's better to compact before it gets out of cache. I think new versions of Claude Code can do that automatically. It can be cheaper if you switch to Haiku or something

Newer versions of CC do in fact compact when the cache is close to expiry. I haven’t seen it work 100% of the time but it does it most of the time

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You could use a dumber model (luna or haiku) for compact to get around this

I do this + caveman and my allowed usage lasts longer.

That’s forced refilling the cache under a different model.

You are correct, the first turn costs about the same either way, the difference comes after. Without compacting, every later turn re-reads the non-compacted context, and after compacting it reads a short summary.

So it only pays off if the session goes on. In my own dogfooding tests, I compacted 47 times out of 50 it had suggested.