Comment by CGamesPlay

That's fair (although it doesn't have anything to do with getting "real root" in a userns in that case). I guess one approach would be something like modifying the host's logrotate binary and waiting for it to trigger, or something like that. Would escape the container to root on the host directly. I imagine it wouldn't be a sure thing to pull off, either, but definitely straightforward enough that any APT should be asking Claude to develop it.