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Ah yes, the autoproxy .pac file config file. I have a few that we toyed with using at work if it helps.
The question then becomes: is it more of a PITA to change IE proxy settings (unless you have an automated way [GPO] of doing this) on all PC's instead of doing something on the server side?
I'd look into the firewall on your OS as that might be easier. eg: Just setup some rules that look for outbound traffic to the target IP's then redirect the requests to your gateway.
-r
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