Upgrade Windows Server 2012 to Server 2019

Reading Time: 3 minutes

Microsoft recommend upgrading your server OS to the latest version, but this is not always possible. Your business may be running third party applications that are not compatible with later Windows Server Operating Systems.

Before upgrading, always check whether the applications running on your current Operating System are supported. It will save you a lot of time and disappointment.

So let’s continue on the basis that you have carried out your checks and the applications currently running on your server supports Server 2019.

Firstly, ensure you have a full backup of your server, so in the event the upgrade goes horribly wrong, you have a backup.

Note: If you have Microsoft Endpoint Protection installed, you will be prompted to remove this app. This app is not compatible with server 2019

Now, that you are all set, you may be thinking, can I upgrade directly from server 2012 or server 2012 R2 to Server 2016? The answer is yes, you can and it’s a supported method. See support matrix from Microsoft below. So whether you decide to upgrade from Server 2012 to 2019 or from 2016 to 2019 a one hop in-place upgrade is supported.

Available in-place upgrade paths

Ok, so we now have a full system backup, and we know that third party apps are supported with server 2016/2019.

Before we get started with the upgrade, Microsoft recommend that you collect some information from your device, for diagnostic and troubleshooting purposes. Because this information is intended for troubleshooting purposes only, store the information at a location where it’s easy accessible and not on the server being upgraded.

To collect your info

  1. Open a command prompt, go to c:\Windows\system32, and then type systeminfo.exe.
  2. Copy, paste, and store the resulting system information somewhere off of your device.
  3. Type ipconfig /all into the command prompt, and then copy and paste the resulting configuration information into the same location as above.
  4. Open the Registry Editor, go to the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion hive, and then copy and paste the Windows Server BuildLabEx (version) and EditionID (edition) into the same location as above.

Upgrade Server 2012 to 2019

1) Patch your server with the latest windows updates if not already up to date
2) Locate the Windows Server 2019 Setup media, and then select setup.exe
3) Select the Windows Server version you wish to upgrade to

Screen to choose which Windows Server 2012 R2 edition to install

4) Accept the licensing terms

Screen to accept your license agreement

5) If you’re running Microsoft Endpoint Protection on your server, setup will prompt for this app to be removed as it isn’t compatible with Windows Server 2019

6) Select Keep personal files and apps, and then select Next

Screen to choose your installation type


7) After Setup analyses your server, setup will prompt you to proceed with your upgrade by clicking install

Screen showing you're ready to start the upgrade

8) Wait for the upgrade to complete

Screen showing your upgrade progress

9) To ensure the upgrade completed successfully

– Open the Registry Editor, go to the HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\WindowsNT\CurrentVersion hive, and view the ProductName. You should see your edition of Windows Server 2019, for example Windows Server 2019 Standard. Make sure all of your applications are running and that your client connections to the applications are successful.

If you think something might have gone wrong during your upgrade, copy and zip the %SystemRoot%\Panther (usually C:\Windows\Panther) directory and contact Microsoft support.


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