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From the information scattered around the Internet, it seems that running Windows as a host OS and also installing it as a guest OS somewhere using the same key is okay so long you don't use both at the same time.

I'm looking to migrate to Linux and I'd like my host OS to be say Ubuntu for starters and my guest OS to be Windows. My computer came with Windows 8.1 Home OEM licence and I clean installed Windows 10 Home when it came by which I got the free upgrade and the Windows 10 install was activated just by the virtue of running on the same hardware, I didn't have to enter my key again and a generic key is shown in Windows 10.

Given that I upgraded the OS and that the host OS I aim for will not be Windows, can I use Windows 10 Home with my original key and use it in the VM? Or will I need to install Windows 8.1, activate it with the original key, then upgrade it to Windows 10 and get a free update for the guest OS install again? Do I install Windows 10 straight away and expect it to be automagically activated like my host OS install was? (I expect not, since the HW ID will not be the same.) Can I use Windows with a OEM licence which is for older version as a guest OS when not on Windows host OS at all?

  • Technically it will work and activate legally and per the TOS is an entirely different story – Ramhound Aug 31 '15 at 10:03
  • I assume you mean installing Windows 8 with the original OEM key and then upgrading to Windows 10 will work, right? Since Microsoft said they'll go easy even on people with unlicenced installations and since this is just for personal use, I think I'll be okay with breaking the TOS. – Tomáš Hübelbauer Aug 31 '15 at 12:23
  • Windows 10 license is still going to be an OEM license, locked to the machine the original Windows 8 OEM license cam on it, I simply provided the answer to your question. Due to concerns for being helpful to the entire community I won't actually answering the question. – Ramhound Aug 31 '15 at 12:29
  • Thanks for your comments. I'm not yet privileged to upvote them, will do that once I can. – Tomáš Hübelbauer Aug 31 '15 at 12:32
  • I'm still wondering why licensing and legal questions are not closed as OT Where can I ask about Software Licenses/Licensing? What is the place to ask about legal issues associated with using software? – bummi Dec 18 '15 at 23:34
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In short; It will work, but is not allowed:

As stated on Microsoft.com:

You are required to support the license on that original PC, but you cannot support a license that has been moved from a PC that you manufactured to one that you did not. This is one of the key reasons why an OEM System Builder License can’t be transferred.​​​​​​​​​​​​​​​​​​

If you had a non OEM license it would have been OK to virtualize your Windows, so long as you deactivate the old one.

source: http://www.microsoft.com/OEM/en/licensing/sblicensing/Pages/transfer_oem_licenses.aspx

  • 1
    You can find loyers that support the statement that it is the original computer... those are things that should convince people to run far far away from windows. – Hastur Dec 19 '15 at 6:37
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    It worked for me. I had an OEM Win7-64, upgraded to Win10 and had 'Win10 upgrader's remorse' (Win10 ran slow). So, I duel-booted to Ubuntu, installed VirtualBox, installed Win10. After installing the new Win10, I ran the 'Activation' app and entered the Win7 key printed on the sticker on the bottom of the PC/laptop. Now the Activation app says "Windows 10 on this device is activated with a digital entitlement". – JimFred Jun 25 '16 at 22:28
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    @kazaamjt Hmm, not a lawyer myself, but how does the Microsoft's statement forbid the use of the OEM Windows system inside a VM running on exactly the same machine? Here microsoft.com/en-us/Useterms/Retail/Windows/10/… they say in point 2.d.iv Use in a virtualized environment. This license allows you to install only one instance of the software for use on one device, whether that device is physical or virtual. If you want to use the software on more than one virtual device, you must obtain a separate license for each instance. – racic Nov 4 '17 at 19:42
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    @Racic as the bold part states. The License can't be transfered. If you move to a VM it is still counts as transfering the license. – kazaamjt Feb 23 '18 at 15:02

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