I am not an expert on Windows Activation, but I think that this depends upon what kind of license you have. I know Technet/MSDN install keys allow you to use t

I am not an expert on Windows Activation, but I think that this depends upon what kind of license you have. I know Technet/MSDN install keys allow you to use the same key on up to X different machine "fingerprints" depending upon what type of subscription you have, so in this case I think he'd be OK. It should just look like 2 of X activations on different machines. If you tried doing the same with an off-the-shelf Windows 7 upgrade install or an OEM install, I'm pretty sure you'd run into problems, though, unless the two machines were identical from the point of view of Windows Activation.