While on campus, your computer is on the University network and the update happens automatically.
However, if you're using a managed device at home, you'll need to sign in to the UMD Virtual Private Network (VPN) service on a regular basis to make this connection.
If your computer nears 180 days without "phoning home" to the license server, you will begin to get a Windows popup message that states, "Your Windows license will expire soon." If this happens, sign in to and use the UMD VPN service for the day. When you next sign in to your computer, the pop-up should disappear.