I've been experimenting with s3 caching and ran into this issue.
Turns out it's not new, and there is even a ticket for it: https://github.com/dagger/dagger/issues/11328.
In my experiments caching seems pretty effective, and if it wasn't for this timeout failure would make selling dagger to other teams a lot easier.
I created a PR https://github.com/dagger/dagger/pull/11585, which would help address the problem. It simply introduces yet another EXPERIMENTAL_... variable for shutdown timeout, so it's a safe change.
It'd be very nice to see a fix in the next release, whether it's this or something else.