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Date: Sat, 14 Jul 2012 19:58:32 +0200 (CEST)
From: Wojciech Puchar <wojtek@wojtek.tensor.gdynia.pl>
To: Graeme Dargie <arab@tangerine-army.co.uk>
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Cc: "freebsd-questions@freebsd.org" <freebsd-questions@freebsd.org>
Subject: Re: Squid issue
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> Firstly I know this is a bit off topic for this list, please accept my apologies in advance. I have tried asking in more relevant circles but I have had no responses at all.
>
> Under pfSense I have openVPN running and Squid, the vpn has rules to route traffic on ports 119 and 563 via the
> VPN connection and everything else should route via the normal WAN 
> connection and this works as expected until I introduced Squid to the 
> mix, now web traffic is being routed via the VPN and I can see no obvious 
>options in Squid to force it to use the WAN gateway. If anyone has any 
> ideas or solutions feel free to contact me off list.

tcpdump is your friend

and check

tcp_outgoing_address

in squid config.

it may make difference.

For sure SOMETHING is wrong with your firewall rules, not in squid.

i don't use pfSense (don't even know what it is), but ipfw and mpd, so i 
cannot help you more