Just remember that "System Booting" is not defined by "when does my login prompt appear" but is active until all services have started on your windows box. Also i believe that Roaming VPN is using a dynamic application class that won't actually enforce the 5 minute rule, since it will just give you another 5 minutes if you close the application and open it again, since the "add process to class" rule is enabled in all system states.
