Windows Server Upgrade Paths for All Versions 2022, 2019, 2016

Prajwal Desai
Posted by Prajwal Desai
Windows Server Upgrade Paths

This article will provide a list of Windows Server upgrade paths for each server version, which should be helpful when you’re upgrading a server from one version to another.

In any organization, one of the main responsibilities of system administrator is to ensure a supported version of Windows Server is installed. The older version of Windows Server are typically the ones have reached EOL don’t receive updates from Microsoft. Hence, upgrading a server to next supported version becomes a mandatory task for admins.

One of the things that administrators need to know before they can upgrade servers is the supported Windows Server upgrade paths. I often get emails asking me if a specific version of Windows Server can be upgraded to the latest version. Or is the upgrade to Windows Server 2019 from Windows Server 2012 R2 supported?

Also Read: Supported SCCM In-place Upgrade Paths

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Many of us are confused about this, and we are aware that Microsoft has released different versions of Windows Server. Upgrading a Windows server to a higher version is always confusing. So, I decided to help server administrators by putting all the information about all the ways to upgrade Windows Server in this article.

When you plan to upgrade the Windows Server, Microsoft recommends upgrading to the latest version of Windows Server. You can use the newest features, including the newest security features, and get the best performance by running the most recent version of Windows Server.

Note that you can upgrade to a newer version of Windows Server by up to two versions at a time. For example, Windows Server 2016 can be upgraded to Windows Server 2019 or Windows Server 2022. You must, however, be aware of the proper server upgrade paths when using older versions of Windows Server before carrying out in-place upgrades.

Related Article: Supported Windows 11 Upgrade Paths

Windows Server 2022 Upgrade Paths

Windows Server 2022 is the latest version of Windows Server available as of today. This server version can be upgraded to next two upcoming versions of Server.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2022Upcoming version of ServerYes
Windows Server Upgrade Paths for version 2022

Windows Server 2019 Upgrade Paths

The below table lists all the upgrade paths for Windows Server 2019.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2019Windows Server 2022Yes
Windows Server Upgrade Paths for version 2019

Note: The Windows Server 2019 can be upgraded to Windows Server 2022 and even the upcoming version of Windows Server which could be either Server 2024/2025.

Windows Server 2016 Upgrade Paths

If you are running Windows Server 2016 in your setup, listed below are the upgrade paths.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2016Windows Server 2022Yes
Windows Server 2016Windows Server 2019Yes
Windows Server Upgrade Paths for version 2016

Windows Server 2012 R2 Upgrade Paths

The below table lists all the direct upgrade paths for Windows Server 2012 R2.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2012 R2Windows Server 2022No
Windows Server 2012 R2Windows Server 2019Yes
Windows Server 2012 R2Windows Server 2016Yes
Windows Server Upgrade Paths for version 2012 R2

Windows Server 2012 Upgrade Paths

The below table lists all the direct upgrade paths for Windows Server 2012.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2012Windows Server 2022No
Windows Server 2012Windows Server 2019No
Windows Server 2012Windows Server 2016Yes
Windows Server 2012Windows Server 2012 R2Yes
Windows Server Upgrade Paths for version 2012

Windows Server 2008 R2 Upgrade Paths

The below table lists all the direct upgrade paths for Windows Server 2008 R2.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2008 R2Windows Server 2022No
Windows Server 2008 R2Windows Server 2019No
Windows Server 2008 R2Windows Server 2016No
Windows Server 2008 R2Windows Server 2012 R2Yes
Windows Server 2008 R2Windows Server 2012Yes
Windows Server Upgrade Paths for version 2008 R2

Windows Server 2008 Upgrade Paths

The below table lists all the direct upgrade paths for Windows Server 2008.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2008Windows Server 2022No
Windows Server 2008Windows Server 2019No
Windows Server 2008Windows Server 2016No
Windows Server 2008Windows Server 2012 R2No
Windows Server 2008Windows Server 2012Yes
Windows Server 2008Windows Server 2008 R2Yes
Windows Server Upgrade Paths for version 2008

Note: The support for Windows Server 2008 and Windows Server 2008 R2 has ended. I recommend you update your version of Windows Server to a more recent version as soon as possible.

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Prajwal Desai
Posted by Prajwal Desai
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Prajwal Desai is a Microsoft MVP in Intune and SCCM. He writes articles on SCCM, Intune, Windows 365, Windows Server, Windows 11, WordPress and other topics, with the goal of providing people with useful information.
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