Fix Keep personal files and apps option greyed out during Upgrade

The option to “Keep personal files and apps” during a Windows upgrade or reinstall means that the Server not permitting the user to retain their files and apps while transitioning to a new version of Windows. Therefore, I will show you the steps to fix Keep personal files and apps option greyed out” on Windows. Please see how to enable or disable automatic login on macOS, How to fix Task Scheduler Service Greyed Out in Service MMC, and Import certificates into Trusted Root and Personal certificate store.

To fix this issue, you would also need to meet the requirements for upgrading. Confirm that your current Windows version is eligible for the specific upgrade you are attempting. See this article on why Should you upgrade your Server, and perform upgrade over iDRAC.

Reason Why the Keep personal files and apps option is greyed out

As you can see from the image below, you can’t keep your files, apps, and settings because the version of Windows you’re installing is different from the one you’re currently using”.

There are two possible causes of “Keep personal files and apps” greyed out. Here is how to fix the request to add or remove features on the specified server failed.

• You are trying to upgrade using an ISO file that does not apply to the currently installed release.
• You have redirected Program Files to a different directory using a Registry key. Undo the change in Windows Registry and you will be able to keep the data. As you can see, this is not the case for me.

See how to Bypass unsupported CPU and Processor by upgrading to Windows 11 via Windows Update. And how to reinstall Server Manager and disable Server Manager at startup for all users and login users.

Resolution

The fix to this issue is similar to Performing an in-place upgrade from Windows Server 2016 to Windows Server 2019. Get a Retail version of your ISO as the evaluation ISO does not work for me.

Mount and run the setup file as shown below.

Enter the Product Key! Click on Next to continue.

Select your Operating Systems. See how to Make Your Taskbar Completely Transparent on Windows 11.

Accept the Applicable notices and License terms and click next to continue

As you can see, the option to keep personal files and apps are now available.

Upon clicking on next from the image above. Because we selected the option to check for updates, the system will begin this process.

At some point, it will fail due to these issues “Fix Windows 10 Setup 1809 build 10.0.17763.1 is not supported Error, and How to fix Windows update Install error 0x800700b7“.

But if you have a recent Installation Media, this will not happen. This is because, I am using the ISO image from 2019.

In my case only, upon fixing the above two issues, I have any of the two options to resolve this issue.

As you can see we are ready to install Windows Server 2019 and we have the option to keep our files and app. Isn’t this great? Click on Install

As you can see, the installation is in progress.

I hope you found this guide useful on how to Fix Keep personal files and apps option greyed out. Please feel free to leave a comment below.