I'm trying to transparently proxy HTTP requests in a LAN that is served by a pfSense router over SSH.
So far, I've tried setting up an Ubuntu box outside that network and forwarding everything going outward that's HTTP to redsocks on the outside Ubuntu box which is forwarding to RedSOCKS which then points to a SOCKS server provided by a SSH connection to a box that's also outside the network. This does not work and I am not sure why. Connecting to the socks server directly on an internal machine works but I need the traffic transparently forwarded.
Rough diagram of how I am thinking it is setup.
Client -> Router(pfSense) -> RedSOCKS -> SSH SOCKS -> Outside Internet
Help would be much appreciated.
As for searches I've done: I'm kinda doing what this guy wants to do. I don't want to resort to his solution of installing a proximity on every client computer as that would be a extraordinary massive hassle/compatibility issue for me. http://forum.pfsense.org/index.php/topic,20294.0.html