Susan Bradley has a great tip on her SBS (Small Business Server) Diva Blog for patching, especially in remote operations, but it's more than just patching. Sometimes when you work remotely, over a Terminal Server connection typically for Windows servers, and you apply a complicated install or patch, the operation will break the network connection. Then you need to reboot to finish the patch, but you're stuck because you can't get on.

The answer is to schedule a reboot for an hour or so away before you start the operation. If you're still online in time to reboot manually you can delete the scheduled task, but if it disconnects it should force a reboot, and you'll know when.

I would do this with a command line like this one (and assuming it's 12:30 now):

AT \\servername 123 13:30 "shutdown -r -t 5 -f -d p:99:88"

This says at 13:30 on servername to perform a shutdown and reboot, with a 5 second delay, to force all applications to quit, and to put major code 99 and minor code 88 into the event log for a planned shutdown, and to assign an id of 123 to the task. If you want to subsequently abort the timed shutdown enter "AT 123 /delete"

Obviously you need sufficient privileges on the local and remote computers to do this, but you'd need them to perform the update that causes the whole mess anyway.