Okay, I found a solution that works for me. This may not be the proper way to do it, but it is working. So here's the information I'm running OS X Server 3.0 on Mavericks First Under network settings I have 3 network interfaces 1.2.3.186 1.2.3.187 1.2.3.189 The .186 interface is the primary and active service. For all 3 of these network interfaces I click the advanced button, navigate to the proxies tab and enter the .186 address as the address and 3128 as the port. Now, I opened the Server Admin control panel, (the app called server) and created a website for each of the IPs. I called them proxyone, proxytwo and proxythree. Make sure that you assign the appropriate IP and that they are on port 80! Now this is the squid config setup I ended up going with acl ip1 myip 1.2.3.186/32 acl ip2 myip 1.2.3.187/32 acl ip3 myip 1.2.3.189/32 tcp_outgoing_address 1.2.3.189 ip1 tcp_outgoing_address 1.2.3.187 ip2 tcp_outgoing_address 1.2.3.189 ip3 If you make changes to squid while it's running, be sure to restart it. It's now working perfectly for me, finally. If someone has the "right" way or a smarter way to do this, please let me know. Thanks! -- View this message in context: http://squid-web-proxy-cache.1019090.n4.nabble.com/OS-X-Server-3-0-on-Mavericks-Squid-Multiple-Outgoing-IPs-tp4663002p4663003.html Sent from the Squid - Users mailing list archive at Nabble.com.