If you search on the forums you should be able to find more information, but 
basically you can't currently do this with pfSense because you can't do source 
based redirection.  The underlying firewall "pf" can do it just fine but the 
functionality is not exposed through the pfSense web gui.  I was going to work 
on that but I've been a little too busy lately.

> To: support@pfsense.com> From: [EMAIL PROTECTED]> Date: Wed, 28 Mar 2007 
> 12:50:52 -0400> Subject: [pfSense Support] Transparent proxy to a separate 
> Squid box.> > I'm in the process of (hopefully) migrating from a Linux router 
> running > Shorewall to a pfSense box. One of the things we were able to do on 
> our > Linux router was transparently proxy to a separate machine on our > 
> network running Squid.> > We accomplished this with a mix of iproute and 
> iptables. First, the web > packets on port 80 from any machine except the 
> Squid box are marked for > a separate routing table by an iptables rule:> > 
> iptables -t mangle -A PREROUTING -i eth0 -s ! 192.168.0.12 -p tcp > --dport 
> 80 -j MARK --set-mark 3> > > A routing table was set up for that mark, so the 
> result of "ip route > show table 3" is:> > default via 192.168.0.12 dev eth0> 
> > > On the Squid box, packets to port 80 are redirected to port 8080 with > 
> an iptables rule:> > iptables -t nat -A PREROUTING -i eth0 -d ! 165.78.125.12 
> -p tcp > --dport 80 -j REDIRECT --to-ports 8080> > > > What I have gotten to 
> work with pfSense is a NAT rule to redirect port > 80 to the Squid box. That 
> worked, but probably only because the Squid > box is still using our Linux 
> router as it's default gateway. Otherwise, > I think that once its gateway is 
> set to the new pfSense firewall, it > will try to redirect it's port 80 
> traffic back to itself.> > The other issue I found, is that by using NAT, the 
> Squid logs show the > "source" IP address of the web requests as the IP of 
> the pfSense > firewall - not the local client that is actually making the 
> request. > This will really throw off our usage reporting software, MySAR > 
> (http://giannis.stoilis.gr/software/mysar/). I'm also not sure how this > 
> will affect our MAC address-based ACLs in Squid.> > Being new to BSD and 
> pfSense, I'm not sure if it is even possible to > replicate the setup that we 
> currently have with Linux. Hoping that > someone here can give me some 
> insight on how I can accomplish this or > whether I need to use a Linux-based 
> router.> > Thanks,> > Dave> > > 
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