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My brother has a laptop (using Windows 7) that he really wants to keep secure. Originally, he was not going to connect it to the Internet, but I suggested that I could probably set up a Ubuntu virtual machine for him so that he could still browse the Internet and have the files on the host machine protected. I am planning to use either Virtual Box or VMWare for the virtual machine. Is there anyway that I can restrict internet connections so that traffic is only to either Windows Update or the Virtual Machine?

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For VMWare you can disable IPv4 and IPv6 under the adapter settings this will disable the network on the host but still allow it to be accessed by the VM if it is set to Bridged. You can re-check IPv4 to temporarily enable the internet to allow updates if you are having an issue an update fixes.

Why not just use Ubuntu as the main OS? If you need Windows you should consider running the browser in Sandboxie and/or using something like Rollback rx because a VM will be cumbersome.

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This actually works surprisingly well due to VMWare Unity. You can create a shortcut on the desktop and you can have a running program integrate in with your Windows tasks –  Casebash May 19 '11 at 12:15

There are a few different things that you can do. To distinguish between windows and the virtual machine you can give each system a different static IP address, and then the firewall can assign rules to each of those IP address. You could for example assign Windows 192.168.1.50 and Ubuntu 192.168.5.50. In any case, I wouldn't imagine that you could use the same IP address in both as it would cause problems.

Additionally you can combine IP address information with OS packet fingerprinting. Originally this was done only with pf on the BSD platforms, but it looks like there is support for iptables today.

Furthermore to generate rules for only the Windows Update systems it is possible to use a firewall creation script called mason. It generates firewall rules based on traffic. Although, I suspect that there are many servers involved here and as a result it may be best to just enable all outgoing traffic destined to microsoft.com, unless you have the drive to find all of them.

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