Keep personal files and apps option greyed out when upgrading from Windows Server 2012 R2 to Windows Server 2019

Question

I'm trying to do an in-place upgrade to our Virtual Machine servers from Windows Server 2012 R2 Standard to Windows Server 2019 Standard. I'm using a licensed installation media ISO file downloaded from our MS Tenant's O365 Admin Center. During upgrade, the option to "Keep personal files and apps" is not available for selection. The error message is "Your files, apps and settings can't be kept because you're installing an edition of Windows that's different than the one you're currently using". This is happening even when I tried upgrading to Windows Server 2016 as well (as a troubleshooting test).

I've checked from SysInfo.exe that the Edition of Windows installed on the current environment is Windows Server 2012 R2 Standard.

From Registry path "HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion", the BuildLabEx key has the value "9600.20625.amd64fre.winblue_ltsb_escrow.221003-0335" and the EditionID key has the value "ServerStandard".

I've also tried running PowerShell commands DISM /Online /cleanup-image /scanhealth & /chechhealth & /restorehealth. All has completed successfully without any corruption component store detected.

The "C:\Windows\Panther\setup.evtx" Event Logs file also contains no errors or warnings regarding the upgrade attempt.

I know that it is better to build a new fresh install VM and migrate the apps & files over. However, the servers I am trying to upgrade contains a collection of large DBs and apps that would take weeks to migrate. HELP!!!

Answer 1

Hello

There are two possible causes of "Keep data" is greyed out:

1. You are trying to upgrade using an ISO file that is not applicable to the current installed release.
2. You have redirected Program Files to a different directory using a Registry key. Undo the change in Registry and you would be able to keep the data.

Hope that helps.

Best Regards,

Hania Lian

Answer 2

I ran into this just night. I had a 2012 datacenter server (not R2) and I wanted to upgrade it to 2016 standard and then again to 2019 standard. It wasnt allowing me to choose the keeps personal files and apps. It said "Your files, apps and settings can't be kept because you're installing an edition of Windows that's different than the one you're currently using". I HAD to install 2016 datacenter and then 2019 datacenter to keep personal files and apps.

Answer 3

Hi Hania,

I have two servers, both domain controllers for separate domains and both are listed as ServerStandard in the registry. Both servers are currently updated and running 2012 R2. The program files directory is not redirected. The ISO I'm using is the Server 2019 image downloaded from the official Microsoft evaluation and I'm selecting Server Standard with the desktop experience when installing. Neither will let me preserve files and settings. Is there something else I can look for?

Thank you in advance,

John

Answer 4

Do not upgrade Domain Controllers in place, rather, spin up a new VM, using OS version of your choosing and license of which you have, then promote to DC and migrate FSMO roles to it.

That is the way.

If those are your only DCs, spin up a fail-over VM in Azure with DC role, with s2s VPN, of course.

Answer 5

Hi John,

Not sure if you already have a solution but I was having the same issue and found a post on Server Fault that had the answer.

All credit goes to joat

The original post is on Server Fault.
Here is the URL. Upgrade windows server 2016 to 2019 , Evaluation ISO is not prompt for a license key during the installation - Server Fault

“Winning Response” by joat

I had the same issue and I resolved it by mounting the ISO and changing the edition.

After copying the ISO files to a folder I ran the following:

dism /mount-wim /wimfile:c:\ISO\sources\install.wim /mountdir:c:\mount /index:2

dism /image:c:\mount /get-currentedition

dism /image:c:\mount /get-targeteditions

dism /image:c:\mount /set-edition:ServerStandard

dism /unmount-wim /mountdir:c:\mount /commit

Then I ran the setup file and it still listed eval under the options, but then it allowed me to choose to keep my files.

Commands 1, 4 and 5 took several minutes to complete.
Also, the directory (c:\mount in the example) needs to exist. dism won’t create it.
If you want to verify, run dism /image:c:\mount /get-currentedition again before running the last command.

To make an ISO I used Imgburn but you should be able to do it with just about any (quality) disc burning software.

This worked like a charm for me. Hope it helps you too.