Thanks for the previous post I made the suggested changes to squid.conf but I still can not connect. Now on the Web browser I am getting Failed to establish a secure connection to owaServer The system returned (71) Protocol error On the squid server I am seeing a bunch of the following fwdNegotiateSSL: Error negotiating SSL connection on FD 12: error: 14090086: SSL routines:SSL#_GET_SERVER_CERTIFICATE: certificate verify failed (1/-1/0) Is this a configuration error with Squid or an issue with my certificates. I have one SSL certificate for mail.myco.com which I purchased for the Exchange server. Following the instructions in a previous post I exported the certificate on the Exchange Server, copied the pfx file to the Squid server and used openSSL to convert it to a private pem file which I stored in etc/ssl/private , a public pem file which I stored in etc/ssl/certs and a server.key file is stored in etc/ssl below is the current squid.conf file acl manager proto cache_object acl localhost src 127.0.0.1/32 ::1 acl to_localhost dst 127.0.0.0/8 0.0.0.0/32 ::1 acl localnet src 25.0.0.0/8 # RFC1918 possible internal network acl SSL_ports port 443 acl Safe_ports port 80 # http acl Safe_ports port 443 # https acl Safe_ports port 25 # acl CONNECT method CONNECT http_access allow manager localhost http_access deny manager http_access deny !Safe_ports http_access deny CONNECT !SSL_ports https_port 25.36.2.33:443 accel cert=/etc/ssl/certs/mail.myco.com.pem key=/etc/ssl/server.key defaultsite=mail.myco.com cache_peer 25.36.2.32 parent 443 0 no-query originserver login=PASS ssl sslcert=/etc/ssl/certs/mail.myco.com.pem sslkey=/etc/ssl/server.key name=owaServer ** I tried the above line with connection-auth=on (and off) *** I tried both of the followin lines at different times *** acl OWA dstdomain mail.myco.com acl OWA dst 25.36.2.32/32 cache_peer_access owaServer allow OWA never_direct allow OWA http_access allow OWA http_access allow localnet http_access allow localhost # Squid normally listens to port 3128 http_port 3128 # Uncomment and adjust the following to add a disk cache directory. cache_dir ufs /var/cache/squid 100 16 256 # Leave coredumps in the first cache dir coredump_dir /var/cache/squid refresh_pattern -i (/cgi-bin/|\?) 0 0% 0 refresh_pattern . 0 20% 4320