The last two times I've reset this server, once via remote desktop and once via the Windows Update nag window (also over TS), according to the event log the shutdown has proceeded normally (up to the event logger shutting down), but then it never comes up again. Going to the console itself we find a black screen with a blinking cursor, and it stays that way overnight, until we finally pull the plug. Normal startup after that.
What sort of thing could cause this to start happening? I'm not aware of any major or deep changes to the system (the first time this happened was not on a Windows Update run.)