Can I install my copy of Windows 7 into a virtual machine running that same copy?

In this excerpt from
Answercast #86, I look at possible problems in trying to do a double-install
of Windows onto one machine using Virtual Machine technology.

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Re-install a copy of Windows 7?

Unfortunately, there’s no clear answer to this particular situation that you find yourself in. The best I can say is, “Maybe.”

There are two components to that “maybe.” One is technical; one is legal.

Driver problems

So you’ve got a DVD installation that came with your OEM system. If that DVD has been configured specifically for Dell machines, it is possible that it may not have the right drivers to work in a virtual machine. The virtual machine even though it’s running on your Dell machine, won’t be actually appearing as a Dell machine to the software that runs in it. It appears as a generic virtualized PC that has generic drivers.

It may work; it may not work. It is possible that it may not work because it’s a Dell specific installation media being installed on something other than a Dell; a virtual machine.

License agreement

The other aspect of this, of course, is the legal one. This is where I would have you take a look at the license agreement that we all love to skip over when you’re installing software. It is possible that the license agreement specifically calls out installing it on exactly one and only one computer.

Now, what does that mean when it comes to virtual machines?

I honestly don’t know.

Is a virtual machine another computer? Well, technically it kind of is – and technically it kind of isn’t. It’s a second installation of Windows, from the same copy, simultaneous with the original installation of Windows.

That’s probably in violation of a one-install license agreement.

Try and see

Again, I’m not a lawyer; I can’t say for sure. What I would probably do is have you try it and see how it works, to begin with. As far as the legal side of things are concerned, I really don’t think that this is one of those things that’s going to get you into any trouble.

I can’t promise it obviously. Again, I’m not a lawyer; I have to cover my butt on that – but it’s the kind of a thing that I would feel comfortable trying.

Licensed copies

Now, as to what I specifically do? I have the luxury of actually installing separately licensed editions of the various versions of Windows in virtual machines.

So on my Windows 7 machine, which came with a pre-installed copy of Windows, I have installed Parallels, the virtual machine technology – and have several different virtual machines that I can run: Windows XP; a couple of copies of Windows 7; a copy of Windows Vista; a copy of Windows 8.

Those are all separately licensed copies. Usually they’re licenses that I reused over the years.

For example, the copy of Windows XP that I currently run in a virtual machine might actually be a license from a machine that I had up to 10 years ago – that I no longer have. The license in that particular case, is transferable so I can use it on another machine.

In this case, the “other machine” is one of my virtual machines.

So there’s really no clear answer. Ultimately, I would personally feel comfortable just trying it and seeing what works.

(Transcript lightly edited for readability.)