I have configured a Squid3 proxy server on Debian using WCCP to a Cisco 2821 router (via GRE tunnel). Regular HTTP traffic works just fine. Anytime I try to connect to HTTPS, it times out. I've compiled Squid with --enable-ssl. The squid configuration is as follows: #################################################################### # Squid3 Configuration # # # # Cisco Router at 10.50.40.1 # GRE tunnel to Ciso Router at 10.50.1.1 # # Local Squid3 server # name: wwifi-atl-squid1 # IP: 10.50.40.100 # WCCPv2 (Transparent mode) # #################################################################### visible_hostname wwifi-atl-squid1 # cache_effective_user squid squid http_port 10.50.40.100:3128 transparent hierarchy_stoplist cgi-bin ? acl QUERY urlpath_regex cgi-bin \? cache deny QUERY acl apache rep_header Server ^Apache refresh_pattern ^ftp: 1440 20% 10080 refresh_pattern ^gopher: 1440 0% 1440 refresh_pattern . 0 20% 4320 # Access Control List Definitions acl localnet src 10.50.10.0/24 10.50.20.0/24 10.50.30.0/24 10.50.40.0/24 10.50.100.0/24 10.50.201.0/24 acl manager proto cache_object acl localhost src 127.0.0.1/255.255.255.255 acl to_localhost dst 127.0.0.0/8 acl SSL_ports port 443 563 # https, snews acl SSL_ports port 873 # rsync acl Safe_ports port 80 # http acl Safe_ports port 21 # ftp acl Safe_ports port 443 563 # https, snews 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 Safe_ports port 631 # cups acl Safe_ports port 873 # rsync acl Safe_ports port 901 # SWAT acl purge method PURGE acl CONNECT method CONNECT # http allows/denies always_direct allow all http_access allow manager localhost http_access deny manager http_access deny !Safe_ports http_access deny CONNECT !SSL_ports http_access allow localhost http_access allow localnet http_reply_access allow all icp_access allow all debug_options ALL,1 # Following options are for transparent mode wccp2_router 10.50.40.1 wccp2_rebuild_wait on wccp2_forwarding_method 1 wccp2_return_method 1 wccp2_assignment_method 1 wccp2_service standard 0 wccp2_address 10.50.40.100