Hi Brad, I had simliar problems, but I eventually managed to solve them (thx to Henrik) Try this for 2.6 (note I use client certs for authentication *before* the basic authentication starts off) https_port A.B.C.D:443 \ defaultsite=anyhost.anydomain.tld vhost \ cert=/usr/local/etc/squid/certs/anyhost.anydomain.tld.pem \ clientca=/etc/CA/ssl/public/ca.pem \ crlfile=/etc/CA/ssl/public/crl.pem \ options=ALL \ capath=/etc/CA/ssl/public cache_peer W.X.Y.Y parent 80 0 no-query originserver \ front-end-https proxy-only no-digest login=PASS connection-auth=off cache_peer_domain W.X.Y.Z anyhost.anydomain.tld /Cheers Bert.