How to automatically assign a route to client in Windows Server PPTP VPN?

Solution 1:

I haven't actually tried it, but I believe this should do what you want if you're using a windows (?2003+) domain.

At the bottom of the 'Dial-in' tab of the active directory user properties for the user you want to enable it for there's an 'Apply static routes' checkbox, and a button for entering those routes.

Solution 2:

I'd recommend you configure your DHCP server to provide the proper routes to the client via option 121, "Classless Static Routes". The VPN client's DHCP client will send a DHCPINFORM after connecting to the VPN and should receive the routes from the DHCP server. This works in Windows 7 and, if memory serves, in both Vista and XP as well.