I was away from my phone for an extended period of time yesterday, and when I finally did check it, it had auto-restarted. I noticed, however, that my VPN was shutdown and I was 'nakedly' connected to my WiFi. When logging in, the VPN started right up as normal.
It makes sense that the VPN wouldn't start until after first login, but given that I was wondering if there was some setting to make it such that after an auto-restart, WiFi is not enabled so as to protect from a 'naked' connection.