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I'm using OpenVPN on Windows and it installs a TAP-adapter with the ip 10.x.x.x while my local adapter is on 192.x.x.x

Now I know you can redirect traffic to IP addresses via route add dst-ip 192.x.x.x but I need something that works for DNS names such as www.google.com for example.

Basically I want the VPN to encrypt all my connections except when I make requests to www.google.com and as such I figure I’ll need to run a local proxy since it’s a layer above route.

I chose Squid but I don’t really see how I can achieve what I want in Squid’s configuration. Can someone point me in the right direction here?

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There is a Firefox addon called "Foxy Proxy" that supports pattern matching. You could use that to redirect all traffic except that to google.com to the proxy. Similar addons exists for other browsers as well.

I am not aware of a method to instruct the proxy to tell your browser it should make a direct connection for specific domains.

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