I am running OSX with a windows server 2008 guest in Virtualbox. My goal is to route some of the network traffic in the host through the server guest. This is because the win2008 server has a VPN connection to my workplace using a Smartcard solution which can not operate on OSX.

My current set-up is like this:

1. OSX (Host):

   • connected to the internet via en01

2. Win2008 (Guest):

   • connected to the internet using NAT (lan1 in guest)
   • has a SSTP VPN connection to my workplace
   • is connected to the guest using an Host Only Adapter vboxnet0 (LAN2 in guest)

The important part is about the host (OSX). Primarily I want all network traffic to just go through en01. However, all traffic which can only be accessed through the VPN must go through the guest and through the VPN. I have one specific FQDN which can only be accessed through the VPN (say corp.mycompany.com).

I do not know much about networking. I thought I would be able to get it to work by

• bridging together LAN2 and LAN1 but this didn't seem to work
• this: http://archives.aidanfindlater.com/blog/2010/02/03/use-vpn-for-specific-sites-on-mac-os-x/
• using a loopback adapter on WinXP (when I did not have win2008 yet, but this doesn't work because I can't create a PPTP connection)

And I've also read about Routing and Remote Access but I have no idea on how to use this.

Can someone help me in the right direction?