To get around this, I was able to save the credentials prior to logging in, which allowed the Surface to connect to the Wireless before they actually go through the login process, and ensure that it has access to a Domain Controller.
Click on the 'WiFi' option from Network Settings
Click Wireless Properties
Click Advanced Settings
Note: this isn't a scalable solution, and merely designed to get one or two users up and running on wireless devices. This will cause problems if the user's password expires as well.
For a scalable solution, you will need to use Group Policy and define a Service Account username and password.