I am having problems getting through to Hotmail. It seems to happen only when squid is being used as transparent. When I configure browsers to go through the proxy directly, everything works great. It is Squid 2.6.STABLE9 (from source). It just hangs then times out on the following URLs: Mozilla 1.7.12 https://login.live.com/login.srf?id=2&svc=mail&cbid=24325&msppjph=1&tw=900&f s=1&lc=1033&_lang=EN&bk=72886070 IE6: https://login.live.com/ppsecure/post.srf?id=2&svc=mail&cbid=24325&msppjph=1& tw=900&fs=1&lc=4105&_lang=EN&bk=117381 squid -v: Squid Cache: Version 2.6.STABLE9 configure options: '--prefix=/usr' '--exec_prefix=/usr' '--bindir=/usr/bin' '--sbindir=/usr/sbin' '--libexecdir=/usr/lib/squid' '--sysconfdir=/etc/squid' '--localstatedir=/var/spool/squid' '--datadir=/usr/share/squid' '--enable-async-io' '--with-pthreads' '--enable-storeio=ufs,aufs,diskd,null' '--enable-linux-netfilter' '--enable-linux-proxy' '--enable-arp-acl' '--enable-epoll' '--enable-removal-policies=lru,heap' '--enable-snmp' '--enable-delay-pools' '--enable-htcp' '--enable-cache-digests' '--enable-underscores' '--with-large-files' '--enable-referer-log' '--enable-useragent-log' '--enable-auth=basic,digest,ntlm' '--enable-carp' 'amd64-debian-linux' '--build=amd64-debian-linux' 'host=amd64-debian-linux' '--target=amd64-debian-linux' 'build_alias=amd64-debian-linux' 'host_alias=amd64-debian-linux' 'target_alias=amd64-debian-linux' I added these lines to squid.conf and it did not help: acl hotmail dstdomain .live.com acl hotmail dstdomain .hotmail.com acl hotmail dstdomain .msn.com acl hotmail dstdomain .passport.com acl hotmail dstdomain .passport.net acl hotmail dstdomain .hotmail.msn.com header_access Accept-Encoding deny hotmail Other "https" websites work fine with squid, for example I can log in to banking and other webmail sites like gmail. I am routing to squid from the firewall like this: iptables -t nat -A PREROUTING -i eth1 -p tcp --dport 80 -j REDIRECT --to-port 3328 Thanks for any help.