While running VPN1 on the host and VPN2 on a VM linked to the bridged adapter I cannot add a third VPN on a pfsense client linked to the internal network of VPN2 - in that case the Workstation at the end of the chain does not work. In that case, I can finally get two nested VPN's while at home, but I cannot understand why NAT doesn't work if I'm running a VPN on the host, while 'Bridged Adapter' does work. The weirdest thing of all is that at home I cannot even run VPN1 on the host together with a VPN2 on a pfsense VM attached to the Virtualbox's NAT interface - it does work ONLY if I attach the VPN2 pfsense to Virtualbox's bridged adapter. Connecting the Workstation VM to only one pfsense VPN does work, but VPN1 -> VPN2 doesn't.Īs a side note, VPN1 -> Whonix Gateway -> Whonix Workstation does work both on my home and my office networks. It doesn't seem like a DNS only problem, as I cannot open webs even if I type the IP directly. On the contrary, at home I cannot get VPN1 -> VPN2 -> Workstation to work - I can ping IPs (and with a decent latency) but the browser is stuck forever.

When I'm on my office network, the set up works like a charm: pfsense VPN1 is attached to the host NAT pfsense VPN2 is attached to the pfsense VPN1 internal network, and the Workstation VM is attached to the pfsense VPN2 internal network and has full connectivity.

I've set up two nested pfsense VPN clients following step by step mirimir's privacy guides, and I'm facing a very weird problem:

Pfsense vbox