I am going from Windows 8.1 enterprise to Windows 10 enterprise with the same language and both are x64. I don't get the option to keep applications when running the setup.exe. What other things could prevent the keep application options from showing up?

• Edited by ToddAdmin 11 hours 35 minutes ago

Hi,

What's the language? Based on the official information:

If youre running Windows 8.1 Enterprise, Windows 8 Enterprise, or Windows 7 Enterprise and your system language isn't English, Chinese (Simplified or Traditional), French, German, Italian, Japanese, Korean, Russian, Spanish, or Brazilian Portuguese, you can only keep your personal files when you upgrade. You won't be able to keep your apps or Windows settings.

And if the language is fit, it should has the option for you to choose which you want to keep.

To do an in-place upgrade from Enterprise versions of Windows 8 or Windows 8.1

1.Download the Windows 10 Enterprise Insider Preview ISO file for your operating system from the  TechNet Evaluation Center and transfer the file to installation media, like a USB flash drive or DVD.

2.Log on as an administrator to the PC you want to upgrade, right-click the ISO file, and then click Mount.

3.Double-click setup from the mounted ISO file and follow all of the prompts, including choosing what you want to keep and running the upgrade.

4.Sign up for the  Windows Insider Program to stay informed about future preview builds and features.

More information, please read this article:

https://technet.microsoft.com/en-us/windows/dn783436.aspx