That said, compaction feels like an idea that should work reasonably well, but across all of the major providers and agent tools I've used has never actually produced compelling results, to where if I see I'm getting close to the token limit I prefer to start putting a bow on the project and readying it for a fresh start. Even when I provide a detailed compaction prompt it usually focuses on the wrong stuff.
Still works better than compaction.
On another environment I've been doing something roughly similar, but have integrated Hindsight as a kind of all-in-one of the above and am still trying to suss out the best compaction strategy.
Mentioned by the author in a recent HN thread, I'm also experimenting with automating this through a tiny issue tracker called epiq [1] that basically lets the agent sessions themselves file tickets with the follow-on tasks and relevant handoff right in them, and then a dispatcher automatically launches those tickets into new agent sessions.
I assume Anthropic & friends have noticed this as well and will change how they handle long running sessions, so the gap will likely close over time, but this is definitely where things stand today.
Same teamates also post 'Sol deleted my git repo!' or 'Sorry, ignore those 300 PR comments i was just looking!' ~once a month.