Ok, I have been banging my head against a few issues so I'll start with this one. I read on http://wiki.squid-cache.org/ConfigExamples/Chat where I can make MSN Messenger work through Squid. I am trying to allow MSN Messenger (Live) to work through Squid. I believe the issue is around this 502 error... I don't know, completely stumped. My Squid.conf is the following & the access.log error message: ================ BEGIN squid.conf BEGIN ================ acl manager proto cache_object acl localhost src 127.0.0.1/32 acl to_localhost dst 127.0.0.0/8 acl TestPoolIPs src 10.211.213.135 10.211.212.40 acl localnet src 10.0.0.0/8 # RFC1918 possible internal network acl localnet src 172.16.0.0/12 # RFC1918 possible internal network acl localnet src 192.168.0.0/16 # RFC1918 possible internal network acl sclthdq01w src 10.211.194.187/32 # custom acl for apache/cache manager acl SSL_ports port 443 acl Safe_ports port 80 # http acl Safe_ports port 21 # ftp acl Safe_ports port 443 # https acl Safe_ports port 70 # gopher acl Safe_ports port 210 # wais acl Safe_ports port 1025-65535 # unregistered ports acl Safe_ports port 280 # http-mgmt acl Safe_ports port 488 # gss-http acl Safe_ports port 591 # filemaker acl Safe_ports port 777 # multiling http acl CONNECT method CONNECT http_access allow manager localhost http_access allow manager sclthdq01w http_access deny manager http_access deny !Safe_ports http_access deny CONNECT !SSL_ports #http_access allow localnet http_access allow localhost http_access allow TestPoolIPs # MSN Messenger acl msn urlpath_regex -i /gateway/gateway.dll acl msnd dstdomain messenger.msn.com gateway.messenger.hotmail.com acl msn1 req_mime_type ^application/x-msn-messenger$ http_access allow msnd http_access allow msn http_access allow msn1 http_access deny all http_port 3128 hierarchy_stoplist cgi-bin ? coredump_dir /usr/local/squid/var/cache cache_mem 512 MB refresh_pattern ^ftp: 1440 20% 10080 refresh_pattern ^gopher: 1440 0% 1440 refresh_pattern -i (/cgi-bin/|\?) 0 0% 0 refresh_pattern . 0 20% 4320 ================ END squid.conf END ================ ================ BEGIN access.log snippet BEGIN ================ 1249333460.877 167 10.211.212.40 TCP_MISS/502 4074 POST http://gateway.messenger.hotmail.com/gateway/gateway.dll? - DIRECT/65.54.239.21 text/html ================ END access.log snippet END ================ I don't believe that this has anything to do with it now, but just as an FYI I tried to use another 'regex' command: acl msn url_regex -i gateway.dll