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I have a VPN connection on a Windows 7 machine. It's set up to connect to a server in US. Is it possible, and if so how, to setup so that .com destinations uses the vpn interface and .se destinations uses the "normal" connection?

Edit (clarification): This is for outbound connections. I.e. the machine conencts to a server on and uses the VPN and the machine connects to and uses the "normal" interface.

Let's say has an IP filter that ensures users are located in USA, if I go through the VPN I get a US ip and everything is fine. But tif all traffic goes this way the server that has a IP filter ensuring users are in Sweden will complain. So I want to route the traffic depending on server location. US servers through VPN and others through the normal interface.

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The problem is that normal routing tables use IP addresses, while you're trying to make the decision based on the domain name. I don't believe there is anything built into Windows that can do what you want. Perhaps, if you're just trying to access web pages, try setting up a proxy which will send traffic out the VPN tunnel and then configure your browser to only use the proxy for certain addresses (.com in this instance), and then the rest go out your normal default gateway.

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How would I add the routes to only use the VPN if I find out all the ip addresses used then? i.e (just a bogus ip) – inquam Jan 3 '11 at 21:35
In most browsers, you have the ability to set a proxy server to only be used for certain addresses, and the rest to be direct connections. What I was proposing is that you set your browser to use direct connection for one set of URLs and then proxy for the other. Then either make the proxy or the direct connect use your local default gateway, and then the other one use the PPTP as the gateway. Not sure how well it will actually work in practice, but I don't know of any other way to do what you're looking for. – Dan Jan 4 '11 at 17:28

I assume that you have setup PPTP VPN and that you configured your router to forward the 1723 port to your machine. If you use two domain names that will be pointing to the same public IP you won't be able to do much. Only chance you got is to use different ports in your router forwarding configuration. Also you should try looking into TeamViewer

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I don't mean that the machine will listen to different connections, it will make connections to different servers. – inquam Jan 3 '11 at 9:04
up vote 0 down vote accepted

I ended up using a specially configured dns server to forward some traffic to a overseas vpn to accomplish this.

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