<snip> When debugging a Bittorrent problem, I have happened to notice that the XP box is sending port 80 traffic directly to the firewall, where it is being dropped (as it should). This only seems to happen with Bittorrent, as the rest of the time web browsing from the XP box seems to correctly use the proxy. Any idea how/why this might be happening? Any other information that I could provide that might be useful? <snip> This is not a squid problem. The problem is that Bittorrent doesn't know about the proxy server and hence tries to make a direct connection to the website, where it gets blocked by your firewall. Perhaps to force all 80 traffic via the proxy (transparent proxying) and then any traffic on port 80 traffic gets cached? You will have to setup your proxy server differently though and play around with your firewall rules. Cheers Nolan