Multiple VPN's Simultaneously

Hey all,

I already know I can run multiple VPN's through each other. so VPN through a VPN essentially but what I would like to do is set up an edge device (pfSense or something similar) that allows me to have multiple VPN's running at the same time for different networks that allows all PC's on my internal network the same connectivity.

I already know I can do this for internal user like satellite offices connecting to a HQ but I'm looking to be able to do it where I have an external IP in destination countries. So where I want to browse to a specific UK based site all traffic goes through UK VPN. Where I browse to a specific US based site all traffic goes through US VPN and where I want to go to a local site I don't use any VPN's.

Is this something that can be done?

So what you want is for certain websites to use a certain VPN connection automatically? That would be pretty difficult to set up I think. In pfsense you can make firewall rules which will force traffic matching that rule to use a certain gateway. I've used this so that my gaming pc and mail server would use the normal internet connection and everything else used the VPN. I imagine you could do the same thing with external IPs too but most websites have multiple IP addresses so unless you knew all of the IPs for a website it wouldn't work all of the time.

The hard part about this is that you have to know what sites are hosted where before you know where they are...

You can do a geoip lookup to tell where in the world an IP address is physically located. But to get that IP address, you have to do a DNS lookup. The DNS servers tell you a different IP based on where you are asking from. But you don't know where to ask from yet...

I don't see how you could do this unless you have a simple set of rules you would like to use; for example: *.co.uk uses UK VPN, everything else uses a US VPN; or something to that effect.

This is just a guess so I don't know if it's actually possible, but you could try setting up a proxy server and getting it to direct traffic to certain URLs to the different gateways. The trouble with using Pfsense or something like that is that it only deals with things on the IP level, so you can't tell it to send YouTube to the us VPN unless you know every IP that YouTube uses. Whereas a proxy server looks at the URL so if you can get it to send traffic to a certain connection then that might be a good way of doing it.