Topic pretty much says it...most sites work fine using my below set up, but some (Apple's app store) do not. I'm wondering if cert pinning is the issue? Since this set up is basically two separate sessions, I packet captured both. The side the I have control over gives me a TLS Record Layer Alert Close Notify. I am unable to decrypt the other side as the device in question is an iDevice and I can't capture the master secret. I've even tried to ACL certain sites to not bump, but they don't go through. Below is my complete setup. This is running the below: Squid Cache: Version 3.4.6 configure options: '--prefix=/opt' '--enable-icap-client' '--enable-ssl' '--enable-linux-netfilter' '--enable-follow-x-forwarded-for' '--with-large-files' '--sysconfdir=/opt/etc/squid' Any assistance with troubleshooting would be wonderful...thank you. James $IPTABLES -t nat -A PREROUTING -i eth0 -s 192.168.1.96/28 -p tcp --dport 80 -j REDIRECT --to-port 3128 $IPTABLES -t nat -A PREROUTING -i eth0 -s 192.168.1.96/28 -p tcp --dport 443 -j REDIRECT --to-port 3129 acl localnet src 192.168.1.0/24 acl SSL_ports port 443 acl Safe_ports port 80 # http acl Safe_ports port 21 # ftp acl Safe_ports port 443 # https acl Safe_ports port 70 # gopher acl Safe_ports port 210 # wais acl Safe_ports port 1025-65535 # unregistered ports acl Safe_ports port 280 # http-mgmt acl Safe_ports port 488 # gss-http acl Safe_ports port 591 # filemaker acl Safe_ports port 777 # multiling http acl CONNECT method CONNECT acl broken_sites dstdomain textnow.me acl broken_sites dstdomain akamaiedge.net acl broken_sites dstdomain akamaihd.net acl broken_sites dstdomain apple.com acl allowed_sites url_regex "/opt/etc/squid/url.txt" acl all_others dst all acl SSL method CONNECT http_access deny !Safe_ports http_access deny CONNECT !SSL_ports http_access allow manager localhost http_access deny manager http_access allow allowed_sites http_access deny all_others http_access allow localnet http_access allow localhost http_access deny all icp_access deny all sslproxy_cert_error allow broken_sites sslproxy_cert_error deny all sslproxy_options ALL ssl_bump none broken_sites ssl_bump server-first all http_port 192.168.1.253:3128 intercept https_port 192.168.1.253:3129 intercept ssl-bump generate-host-certificates=on cert=/opt/sslsplit/sslsplit.crt key=/opt/sslsplit/sslsplitca.key options=ALL sslflags=NO_SESSION_REUSE always_direct allow all hierarchy_stoplist cgi-bin ? access_log syslog:daemon.info common refresh_pattern ^ftp: 1440 20% 10080 refresh_pattern ^gopher: 1440 0% 1440 refresh_pattern -i (cgi-bin|\?) 0 0% 0 refresh_pattern . 0 20% 4320 icp_port 3130 coredump_dir /opt/var