Upgrading from Windows 10 Enterprise Evaluation After It Expires

We’re not ones to usually write DIY tech articles, but we encountered this scenario and it’s much more silly than you think it would be.

Can you upgrade or activate windows 10 enterprise evaluation after it expires? In short… No.


This scenario starts from using windows 10 enterprise evaluation edition as a fresh install without any prior windows versions installed. There is no simple activate even if you have already purchased windows 10.

  1. You’ll notice when you go into your settings, updates & security, and then the activate tab… you’ll find when you attempt to activate it, you simply won’t be able to. There will be no place to manually input a new product key. And even when we managed to get to the product key input through command prompt, it wouldn’t validate it. Reason by Microsoft is, is that it does not match the product even though you probably already purchased Windows 10 alone. We’ve confirmed this by calling their support team and through trial and error.
  2. If you haven’t already, you’ll want to SAVE all of your data that you had on your evaluation edition on a separate external hard drive or in the could. You should be able to do this even if your trial has expired. (usually windows will still boot for 15 days after but will shut down automatically within 2 hours)
  3. Purchase windows 10 home or pro edition off of Amazon if you still need it. You’ll want to then follow the directions to download to a USB and format it so that you can do a clean install once again.
  4. Once you’ve done that, you’ll want to insert your usb with windows 10 on it to the computer you wish to “reinstall” it on. Get to your BIOS menu on your computer which varies by brand. Usually with one of the f keys but we had to actually hold the delete key down. Once at the BIOS menu make sure to select that it boots from the usb that has windows 10 on it. Once selected it will restart and will run you through the installation process. You’ll actually be able to insert the product key and it will accept!
  5. After it is installed you’ll have to again access the bios menu. Select to boot from the hard drive instead.
  6. You’re finished! Enjoy Windows 10 or loathe it :p

We hope you found this information useful as we could not find this information on the web at time of need. There is a lot of information about upgrading from previous versions of windows but not a fresh install on the enterprise evaluation (and after it expires).

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