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I have Windows 8.1 Enterprise and I wanted to install the Windows 10 Enterprise evaluation (from https://www.microsoft.com/en-us/evalcenter/evaluate-windows-10-enterprise). I don't want to wait until the IT team at our company decides to give us the official update and I rather just install it and in a few weeks I'll get the key from them.

Now, I downloaded the evaluation version ISO but when trying to install it (mounting the ISO file and double clicking setup.exe) it tells me that the versions are different and that I cannot keep any of my files or apps if I continue.

Both versions are Enterprise 64bits and both are in English (US).

Any idea of why that might happen?

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  • "I have Windows 10 Enterprise and I wanted to install the Windows 10 Enterprise evaluation"??? This doesn't make any sense. Please correct your question.
    – DavidPostill ♦
    Jul 30, 2015 at 17:27
  • @DavidPostill Done, I meant Windows 8.1. I know it was very hard to figure out the question with that mistake. Ramhouhd I want to do the opposite, upgrade a Windows Enterprise 8.1 non-trial to Windows 10 Enterprise trial and then enter the key to the evaluation. And the official version has been released: msdn.microsoft.com/subscriptions/securedownloads/?#FileId=64780
    – willvv
    Jul 30, 2015 at 17:34
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    You can't upgrade an evaluation installation. I seem to recall their being something important about next week in connection with Enterprise version. I can't seem to find that article though.
    – Ramhound
    Jul 30, 2015 at 17:38

1 Answer 1

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Updated: Misread the earlier version; updating to reflect further research.

According to the Windows 10 Enterprise FAQ for IT Professionals, you should be able to perform an in-place upgrade:

Can I upgrade computers from Windows 7 or Windows 8.1 without deploying a new image?

Computers running Windows 7 or Windows 8.1 can be upgraded directly to Windows 10 through the in-place upgrade process without a need to reimage the device. You can use System Center Configuration Manager to manage this upgrade automatically through an Operating System Deployment task sequence. See How to upgrade to Windows 10 using the task sequence in System Center 2012 R2 Configuration Manager on the System Center Configuration Manager Team Blog.

(See the second question in the Administration section)

I've looked at a few different public support forums for related reports and there do not seem to be a widespread problems with inline updates for Win10 Enterprise evaluation. I did find one report mentioning that it seems to occur when choosing different country/locale settings than were originally selected.

Traditionally, in-place updates become possible later in the development cycle. Depending on when you downloaded your .ISO (or when it was last updated on your source), it's possible that in-place upgrade is not fully complete.

Since a new evaluation version is either imminent or shortly to be released, perhaps trying again later will provide a cleaner experience.

For those attempting to install the "free upgrade" binaries, per the Windows 10 FAQ:

"Some editions are excluded: Windows 7 Enterprise, Windows 8/8.1 Enterprise, and Windows RT/RT 8.1. Active Software Assurance customers in volume licensing have the benefit to upgrade to Windows 10 enterprise offerings outside of this offer.

(See the answer to "What edition of Windows will I get as part of this free upgrade?")

In other words, I don't think you'll be able to upgrade Enterprise using the free upgrade installation binaries.

Hope this helps...

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  • Yep, that's why I wanted to use the evaluation version of Windows 10 Enterprise. I never intended to get the free upgrade.
    – willvv
    Jul 30, 2015 at 17:31
  • Updated the earlier answer to reflect additional research. Sorry for the earlier confusion.
    – Lance Leonard
    Jul 30, 2015 at 18:05

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