Thanks for the quick reply Yuri, I made a few changes to make sure that I was doing the right thing with respect what port I'm using, and this is my current configuration. Both my certificate as well as my key are in the same file, which from my understanding should work, however I'm sure I'm missing something # Squid normally listens to port 3128 http_port 3127 http_port 3128 intercept https_port 3129 intercept ssl-bump generate-host-certificates=on dynamic_cert_mem_cache_size=4MB cert=/usr/local/squid/ssl_cert/myCA.pem #enables SSL Bumping always_direct allow all ssl_bump client-first all #the following options are dangerous and shouldn't always be used sslproxy_cert_error allow all sslproxy_flags DONT_VERIFY_PEER sslcrtd_program /usr/local/squid/libexec/ssl_crtd -s /usr/local/squid/var/lib/ssl_db -M 4MB sslcrtd_children 5 -- View this message in context: http://squid-web-proxy-cache.1019090.n4.nabble.com/Help-getting-Squid-3-4-Transparent-Proxy-to-Work-tp4669007p4669011.html Sent from the Squid - Users mailing list archive at Nabble.com. _______________________________________________ squid-users mailing list squid-users@xxxxxxxxxxxxxxxxxxxxx http://lists.squid-cache.org/listinfo/squid-users