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At work we have a VPN solution that will only work on windows. I personally do not run Windows at home and run Linux (Ubuntu 14.04). I used Virtual Box to setup a Windows 7 virtual machine to run the vpn software. It works as expected.

My goal is to send my traffic on my main linux host through the windows vm so the proper traffic can be picked up by the vpn. Is this possible at all?

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    I have the same requirement. Because our checkpoint fails to provide a proper linux vpn client. – RobAu Jun 15 '17 at 15:01
  • same problem here - there's a windows only VPN client and I'm running Ubuntu 18.04. If anyone has information that would be hugely helpful. @RobAu – anon58192932 Feb 20 at 22:07
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    @anon58192932 see this answer: superuser.com/a/1219629/113324 – RobAu Feb 21 at 8:03
  • i'm gonna give this a whirl with W10 connection sharing and a second computer so I don't have to use a VM... – anon58192932 Feb 21 at 21:15
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On linux you can define very accurate routing tables that allow you to be connected with several VPN toghether.

I had this problem once, and was solved here.

The problem I see in your case is mainly: "how to use windows as a router?". And probably this is not the best forum where to ask such a question...

Anyway, there are a couple of advices that I guess could be useful: the first is related to Virtualbox networking. I highly suggest you to use 2 virtual ethernet interfaces on your virtual machine:

a) the first one can be a classical NAT interface (default virtualbox), you'll use it as outgoing interface, and will be used by your VPN client

b) a bridged interface on your virtual machine, which will have an IP in the same network as your host machine (i.e. your linux machine).

You should then write routing rules on your host machine that redirect the request on a given IP range (the ones of your corporation VPN) on the virtual machine's bridged interface, i.e. you will define this IP as the gateway for the requests on that IP range.

Then (and this is where I can't help you, sorry) you should write a routing table on your windows machine that redirects all the requests coming on eth1 toward your VNP interface, which is connected to eth0.

I hope this helps. Sorry, but I'm really not an expert on Windows...

Anyway, if you find a proper solution, PLEASE: write the solution here, as it may be useful to many other people.

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Normally not - once a machine (virtual or not) connects to a VPN it behaves as if it is physically connected to that VPN, it is no longer accessible from and can no longer access other machines on the local network (unless conections between the local network machines and any other machine inside the VPN is possible, which kinda defeats the whole purpose of the VPN).

Depending on the VPN implementation it could be technically allowed via config from the VPN server side, look for VPN split tunneling. I doubt a corporate IT would allow it as it's considered a security hole.

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