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OS X Server 3.0 on Mavericks -> Squid -> Multiple Outgoing IPs

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Hi guys, I'm attempting to run squid as a proxy server on my OS X Server 3.0
installation. I have 3 IPs assigned to the machine. I've tried a couple of
different options as seen below to get multiple outgoing IPs to work. What I
would like to happen is if a request comes to 1.2.3.187 then the outgoing
address is 1.2.3.187. So on and so forth with the 3 IPs I have. Here are the
2 configurations I have tried. 

-----Configuration 1------ 

http_port 50.20.213.187:3129 name=3129 
http_port 50.20.213.189:3130 name=3130 

acl tasty3129 myportname 3129 src 127.0.0.1/8 
http_access allow tasty3129 
tcp_outgoing_address 1.2.3.187 tasty3129 

acl tasty3130 myportname 3130 src 127.0.0.1/8 
http_access allow tasty3130 
tcp_outgoing_address 1.2.3.189 tasty3130 

--In the above I'm not sure what src should actually be--- 
If I have source as localhost or the ip of my computer that I'm testing from
ipchicken tells me that my IP is the base IP of the machine .186. 

----Configuration 2--------- 

acl ip1 myip 1.2.3.186 
acl ip2 myip 1.2.3.187 
acl ip3 myip 1.2.3.189 
tcp_outgoing_address 1.2.3.186 ip1 
tcp_outgoing_address 1.2.3.187 ip2 
tcp_outgoing_address 1.2.3.189 ip3 

---In config 2 if I use .186 as my proxy (the base machine address) it works
like a charm via proxy settings thru another computer's firefox or if I do
something like curl --proxy 1.2.3.186:3128 --trace - www.whatsmyip.us 

However if I try to replace .186 with .187 I get a weird index of html page
via a browser or via terminal with curl I get a message that says:
Connection #0 to host 1.2.3.187 left intact 

I'm new to this so I'm probably missing something so basic it's laughable.
But if anyone out there has an idea of what I could be doing wrong, I would
greatly appreciate it. I haven't been able to find a guide for the mac
that's complete but I assume in network I would need an ethernet interface
for each IP. (Which I have) Not sure what other settings need to be setup
there though. Proxy Settings? If so what should the settings be? 

Thanks in advance



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