Yes, it is possible to perform an in-place upgrade of Windows Server 2012 R2 to Windows Server 2019. An in-place upgrade involves installing a new operating system on top of the existing one, preserving the configuration, data, and applications.

To perform an in-place upgrade from Windows Server 2012 R2 to Windows Server 2019, you will need to follow these steps:

  1. Back up your server: Before starting the upgrade process, it is important to back up your server to protect against data loss in the event of any issues.
  2. Download and mount the Windows Server 2019 installation media: You will need to download the Windows Server 2019 installation media and mount it on your server.
  3. Run the setup program: Once the installation media is mounted, run the setup program to begin the upgrade process.
  4. Accept the license terms: You will need to accept the license terms before the upgrade can proceed.
  5. Choose the installation type: Select the “Upgrade: Install Windows and keep files, settings, and applications” option to perform an in-place upgrade.
  6. Follow the on-screen instructions: The setup program will guide you through the rest of the upgrade process.

It is important to note that an in-place upgrade may take some time to complete, and it is possible that some applications or hardware may not be compatible with the new operating system. You should carefully test and validate your applications and hardware after the upgrade to ensure that everything is functioning correctly.

The chart below details the operating system’s supported upgrade paths, as per Microsoft.


Remember to take into account the roles and applications that the servers have installed. You should check compatibility with your application developer to make sure that once upgraded, the applications will work correctly and be supported.

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