Windows Server 2012 to Windows Server 2019 Upgrade

Windows Server 2012 is in an Extended support period. The Extended support for Windows Server 2012 will end on 10th October 2023. That leaves us with a limited time to plan for migration, upgrade or extension of support for Windows Server 2012.

You may decide to extend support for Windows Server 2012 for up to 3 years. For this to happen, you will need to buy the Extended Security Updates (ESAs) for Windows Server 2012 from Microsoft. You could buy ESAs for a period between 1 year to 3 years. As part of the Extended Security Updates, you will be entitled to receive security updates. These ESAs will resolve vulnerabilities that have been rated as ‘Critical’ or ‘Important’ for Windows Server 2012.

You could also consider upgrading Windows Server 2012 to a newer version that is supported well at this point. Or, you could decide to bring up a new Windows Server 2022 and migrate your data and domain controller roles to the new server. For our study, we focus on the upgrade paths available for Windows Server 2012 as we write this.

Upgrade from Windows Server 2012 to Windows Server 2019

In-place upgrades allow the Windows Server 2012 to be upgraded to Windows Server 2019 or Windows Server 2016. This ensures that your server roles are retained. And, all the user data on the server is retained as well.

You can upgrade from Windows Server 2012 to Windows Server 2019. Before upgrading to Windows Server 2019, you will need to upgrade to Windows Server 2012 R2. There is no direct path for upgrading from Windows Server 2012 to Windows Server 2019. Windows Server 2012 R2 will have to be your focal point for upgrades to Windows Server 2016 or Windows Server 2019.

As for licensing, you can use the trial key to upgrade to Windows Server 2012 R2. From here on, you can upgrade to Windows Server 2019 and activate the server using the newly acquired license for Windows Server 2019 license.

The important thing to note over here is that the hardware requirements for Windows Server 2019 need to be taken into account before attempting an upgrade from Windows Server 2012 R2 to Windows Server 2019. There are no changes in hardware requirements between Windows Server 2012 and Windows Server 2019. But, the Windows Server 2019 with Desktop Experience does need 2 GB RAM. Windows Server 2019 needs 512 MB RAM for installation or upgrade.

License Keys – Windows Server 2012 to Windows Server 2019

The upgrade from Windows Server 2019 to Windows Server 2019 needs to be split into two steps:

  • Upgrade from Windows Server 2012 to Windows Server 2012 R2 on a trial key.
  • Upgrade from Windows Server 2012 R2 to Windows Server 2019. You can continue to run on the trial key. Once you are set, you can activate the Windows Server 2019 by purchasing the server licenses.
  • Aside from buying the server licenses, you will also need the new Device CALs or client licenses to work with Windows Server 2019.

If you follow the upgrade plan stated above, you will need the license keys once the server has been upgraded to Windows Server 2019.

Windows Server 2012 to Windows Server 2019 Upgrade Checklist

Before attempting an upgrade from Windows Server 2012, it would be appropriate to perform some basic checks:

  • Ensure that the server hardware is compatible with the requirements for Windows Server 2019.
  • Take backups of the Windows Server 2012 and user data before initiating the upgrade.
  • Plan for the DEVICE CALs or the client licenses needed to work with Windows Server 2019 upgrade.
  • A fresh or clean install needs 32 GB of available disk space. For performing an in-place upgrade, you should plan for at least 60 GB of available disk space. Since you are performing an in-place upgrade, you need to make sure that the disk space availability does not become a constraint. The more disk space, the better it is for the upgrade to Windows Server 2019.
  • Download the ISO image of Windows Server 2019 from the Microsoft site for an in-place upgrade. Do not use the DVD ISO image to attempt an in-place upgrade, unless it is a certified Windows Server 2019 installation media. It will not complete if you are using a DVD image to try an in-place upgrade.
  • Most issues in performing an in-place upgrade from Windows Server 2012 R2 to Windows Server 2019 would be on account of lack of disk space or issues with the ISO image of the Windows Server 2019 files.
  • At a bare minimum, we suggest that you should have 2 domain controllers for the in-place upgrades to be successful. Running in place upgrades on a single domain controller installation is a pretty risky proposition. Obviously, you could take domain controller backups on the cloud. But, single domain controller setups should be evaluated against in-place server upgrades.

It may be a good idea to speak to your MSP and arrive at the best strategy for upgrading Windows Server 2012 to Windows Server 2019 through Windows Server 2012 R2.

Summary

Windows Server 2012 can be upgraded to Windows Server 2016 or Windows Server 2019 or Windows Server 2022. Most companies are happy to upgrade to Windows Server 2019 as it has a proven record. Windows Server 2022 is a new server, and most system administrators are happy to wait until the server has a longer track record of performance and stability.

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