Looks like I spoke too soon... when tracing my nice new proxy on 24.69.177.112, it seems that it's actually going through the primary IP after all: curl --proxy 24.69.177.112:3128 --trace - www.ipaddressworld.com Your computer's IP address is: 24.69.160.243 Anyway, I changed to the previous method I was using, and it seems to report correctly: acl ip1 myip 24.69.160.243 acl ip2 myip 24.69.177.112 tcp_outgoing_address 24.69.160.243 ip1 tcp_outgoing_address 24.69.177.112 ip2 curl --proxy 24.69.177.112:3128 --trace - www.ipaddressworld.com Your computer's IP address is: 24.69.177.112 Much better. Now, if I could only convince my ISP to give me more than one proxy. Ack! Another barrier! thanks again, Amos. Cameron Knowlton At 10:30 AM -0800 09/11/18, Cameron Knowlton wrote: >Eureka! Finally found the problem, it was with a different setting within Squid (SquidMan, actually)... I've posted my squid.conf below in its entirety in hopes that it might help others. and, now the promised and updated squid.conf (I'm so excited, I forgot to include it): # ---------------------------------------------------------------------- # WARNING - do not edit this template unless you know what you are doing # ---------------------------------------------------------------------- cache_peer %PARENTPROXY% parent %PARENTPORT% 7 no-query no-digest no-netdb-exchange default cache_dir ufs %CACHEDIR% %CACHESIZE% 16 256 maximum_object_size %MAXOBJECTSIZE% http_port %PORT% visible_hostname %VISIBLEHOSTNAME% # http_port 24.69.160.243:3128 name=A # http_port 24.69.177.112:3128 name=B # acl fromA myportname A # tcp_outgoing_address 24.69.160.243 fromA # tcp_outgoing_address 24.69.160.243 !all # acl fromB myportname B # tcp_outgoing_address 24.69.177.112 fromB # tcp_outgoing_address 24.69.177.112 !all acl ip1 myip 24.69.160.243 acl ip2 myip 24.69.177.112 tcp_outgoing_address 24.69.160.243 ip1 tcp_outgoing_address 24.69.177.112 ip2 cache_access_log %ACCESSLOG% cache_log %CACHELOG% cache_store_log %STORELOG% pid_filename %PIDFILE% hierarchy_stoplist cgi-bin ? acl QUERY urlpath_regex cgi-bin no_cache deny QUERY # access control lists %ALLOWEDHOSTS% %DIRECTHOSTS% acl manager proto cache_object acl localhost src 127.0.0.1/255.255.255.255 acl SSL_ports port 443 563 8443 acl Safe_ports port 80 81 21 443 563 70 210 1025-65535 280 488 591 777 acl CONNECT method CONNECT # only allow cachemgr access from localhost http_access allow manager localhost http_access deny manager # deny requests to unknown ports http_access deny !Safe_ports # deny CONNECT to other than SSL ports http_access deny CONNECT !SSL_ports # client access http_access allow localhost %HTTPACCESSALLOWED% http_access deny all # direct access (bypassing parent proxy) %ALWAYSDIRECT% always_direct deny all