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I have a single license for Windows 8, which I installed within Parallels. I wondered if I am allowed to clone this VM, or create another using the same key, on the same Mac? I think cloning would work technically with problems since Windows would not think the hardware was different, but I'm not sure legally.

Does it make a difference if I run both VMs at once, or only allow one to be running at any time?

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I haven't tried this with Parallels, but I've cloned a VMWare Windows VM before. Before the clone, the VM was licensed. After the clone, the new machine worked, but was not licensed.

When you clone a machine, some of the VM's hardware IDs change. Mainly, the MAC address of the network adaptor is changed. This is a necessary change, otherwise network errors would occur. With these changes, Windows is able to detect that it's been moved/copied to a new machine.

If you were able to create an exact copy of your initial VM, you may be able to get around this. However, running both copies at the same time would cause errors and Parallels would probably not allow it.

Legally speaking, I would think you would need a separate license for each VM (exact copy or not).

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