I guess I have to start by apologising for the title pun there, but I have been able to hook up Tor with pfSense – in a way – in order to access system in the UK while looking like my connection is in the UK. Unfortunatly, it’s just not as neat as I would like.

I have a very minimal Damn Small Linux virtual machine with Tor and Polipo installed, with Tor configured to use strict exit nodes in the UK (this website helps find some good exit nodes and google can help you modify your torrc file). I can now manually set any machine on my LAN to use the polipo server as a SOCKS proxy server (default port 8118) and it works like a charm.

I have also been able to enable Squid on my pfSense router to use the Polipo server as a parent proxy. This then means I can switch Squid into transparent mode (also known as intercepting mode) to automatically push HTTP and HTTPS connections through to Polipo and then on to Tor. Unfortunately, Squid doesn’t work with SOCKS and so cannot use Tor as a direct parent proxy.

This is still missing my goal by a bit, but is sufficient enough for my purposes for now. Getting Tor to run directly on the pfSense box, and setting up so that only some connections (via a pre-defined list) are automatically forwarded to it, are still the the end-game.