How can I make a Windows Server 2008 RC2 server, auto connect to a vpn when it boots?
Create a batch file/vbscript that automates a standardized VPN connection with given credentials. You can have the task run at boot so it auto starts.
If you have two factor authentication, it may be much trickier (ie: photo grid card, key chain dongle). If its the photo grid you could also code that into the batch file as static variables.