Microsoft is doing cool things with Windows Server with what was originally server core and is now the base version of Windows Server. Combined with Powershell remoting and there’s a lot of power from the command line. Unfortunately, is surprisingly difficult to tell if updates are available and to trigger their installation. If you’re not using SCCM, you can run sconfig.exe and select option 6 to manage your updates but packages and applications pushed through SCCM don’t show up there.