VPN mobile phone to home, then VPN out?

VPN
1

Is this possible?

Would like to VPN to my home connection to access local files / jellyfin and have adblocking from my Virtualized PiHole, then leave to the internet using a paid VPN service.

I have a spare PC I can run any VMs on and could also setup pfsense on it if it helps.

2

It is all about what gateway you are telling your VPN clients to use. Theoretically, if you set the gateway for your VPN clients to use the second VPN tunnel as their gateway it should be doable. I am not a networking expert by trade but know enough to be dangerous and I tinker a lot. Easiest to probably do if you have separate IP space configured for the incoming VPN.

3

I’ve tried several:

  • PPTP/L2TP - easy to setup. Android & iOS easy handle it
  • OVPN - a bit complicated set-up, but very flexible in terms of available options. Very secure. Separate client for Android and iOS is required.
  • WireGuard - my preference. Easy to set-up and secure enough. If you would like to push routes over tunnel - unfortunately no possible.Separate client for Android and iOS is required.

All three option require to have “white IP” which is visible over internet. Be prepared to set-up strong firewall rules to avoid intrusions and attacks.

4

I have not tried that but I’m doubtful it would work on an iPhone - I’ve never been able to run two VPN configurations simultaneously. Can’t speak to Android though.

That being said, I’m accomplishing almost the same thing through a slightly different approach. I run OpenVPN server on my OPNsense gateway at home, as well as a permanent OpenVPN client connected to NordVPN (certain traffic is conditionally routed through Nord instead of my ISP, Comcast). When I connect from my phone to the OpenVPN server at my house, my phone gets all of it’s traffic routed to my home network (PiHole ad-blocking, Plex…etc. are available) and any Internet traffic is then routed through the NordVPN tunnel out to the internet.

Phone → Home OpenVPN → NordVPN via OpenVPN → Internet