Hello Everyone, I've successfully managed to configure sslbump with squid-3.HEAD-20121231-r12554. However, I am having troubles in configuring SslBump using Bump-Server-First in Transparent mode. Basically I don't think I have the correct set of directives/configuration parameters in squid.conf to check/test SslBump using Bump-Server-First in Transparent mode. Any help on making this work is much appreciated. Redirecting traffic on port 80 & 443 to squid via iptables, iptables -t nat -A PREROUTING -i $LAN_IN -p tcp --dport 80 -j DNAT --to 192.168.2.1:3128 #iptables -t nat -A PREROUTING -i $LAN_IN -p tcp --dport 443 -j DNAT --to 192.168.2.1:3129 Squid was compiled using the following flags, ./configure --enable-icap --enable-ssl --enable-ssl-crtd --enable-delay-pools --with-openssl=/usr/local/openssl-1.0.0g squid.conf visible_hostname server httpd_suppress_version_string on forwarded_for off acl allow_machine src 192.168.2.200 http_access allow allow_machine acl whitelist dstdomain "/usr/local/squid/etc/custom/whitelisted-domains" http_access deny !whitelist acl blockfiles urlpath_regex "/usr/local/squid/etc/custom/blacklisted-file-extensions" deny_info http://192.168.2.1/error.html blockfiles http_access deny blockfiles acl lan src 192.168.2.0/24 http_access allow lan 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 http_access allow manager localhost http_access deny manager http_access deny !Safe_ports http_access deny CONNECT !SSL_ports # And finally deny all other access to this proxy http_access deny all # Squid normally listens to port 3128 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 sslcrtd_program /usr/local/squid/libexec/ssl_crtd -s /usr/local/squid/var/lib/ssl_db -M 4MB sslcrtd_children 5 always_direct allow all ssl_bump client-first all sslproxy_flags DONT_VERIFY_PEER # Uncomment and adjust the following to add a disk cache directory. cache_dir ufs /usr/local/squid/var/spool 7000 16 256 # Leave coredumps in the first cache dir coredump_dir /usr/local/squid/var/coredumps # Add any of your own refresh_pattern entries above these. 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