Whonix tunnel via pfSense

Hi all, am trying to configure Whonix Gateway to connect to Tor via a pfSense VPN internal network, as follows:

User → VPN → Tor → Internet

Have configured this as follows in Virtualbox:

pfSense VM (VPN) with Adapter 1: NAT and Adapter 2: Internal Network “pfSense”
Whonix Gateway with Adapter 1: Internal Network “pfSense” and Adapter 2: Internal Network “Whonix”
Whonix Workstation with Adapter 1: Internal Network “Whonix”

However, Whonix Gateway isn’t able to connect to the internet via the pfSense VM. Have tested the pfSense VM separately with an Ubuntu VM that connects to the pfSense VM’s internal network and that has no issues connecting.

First I thought it could be a LAN issue on the pfSense VM since it uses a DHCP server and Whonix does not, so I ran

sudo open /etc/network/interfaces.d/30_non-qubes-whonix

on Whonix Gateway and edited the static IP settings to the same gateway as the pfSense VPN and with an IP address outside the DHCP server range. However, that did not fix the problem.

Whonix Gateway/Workstation also works fine when Gateway is directly NAT’d to host internet (with original settings from the above config doc).

Good thinking.

Next step.Test static network. Can you configure the Ubuntu VM to use static networking with the pfSense VM?

…then use these settings for the gateway.

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