Until it sits there and retires till hell freezes over and you don't realize anything is wrong.

And that's the problem with timeouts, everyone has different expectations.

It's hard to go wrong by telling people what's happening and why. "it's taking longer than usual to X" is a fine thing to expose in a UI.

I should have stated my implicit assumption, that the program will tell me that it’s retrying. If I decide it’s not worthwhile I can stop it, sure.

For any user-initiated action, automatic retry seems strictly better than failing on a single timeout.