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I have a Server 2008 web server that has a single network card with a primary IP and several secondary IP's bound to it. When an application running on this server makes requests to the web it appears to be randomly picking one of the secondary IP's. I would have expected it to use the primary IP to make outbound HTTP requests. How do I force it to always use the primary IP address when making requests?

(The application that is making the outbound requests is an ASP.NET web site.)

Please note that I really do mean outbound requests from the web app to other web servers and not inbound requests from a browser.

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I'm not really up-to-scratch on all this, but have you set the 'routes' correctly? howtogeek.com/howto/windows/… –  phalacee Oct 12 '10 at 7:29
    
Also, do these other secondary IP addresses have Primary Gateways set in config? –  phalacee Oct 12 '10 at 7:48
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