Just seems odd. I have put in the following cache_peer <upstream proxy name> parent 8080 7 no-digest no-query no-netdb-exchange default login=<username>:<password> name=proxy cache_peer <upstream proxy name> parent 443 7 no-digest no-query no-netdb-exchange default login=<username>:<password> name=proxyssl and then further down: cache_peer_access proxyssl allow CONNECT cache_peer_access proxyssl deny all cache_peer_access proxy deny CONNECT cache_peer_access proxy allow all So browsing through Squid, onto the upstream proxy on port 8080 works fine. When I try and access login.live.com on port 443/https then I get challenged for my upstream details again - . These details have been confirmed as correct and are the same <username> and <password> as they always have been. I must be missing something simple then if there is no bug. GJE