This article will provide a list of Windows Server upgrade paths for each server version, which should be useful when performing a direct server upgrade from one version to the next.

In any organization, one of the main responsibilities of a system administrator is to ensure a supported version of Windows Server is installed, and it is patched with the latest updates. The older versions of Windows Server are typically those that have reached the end of life and no longer receive updates from Microsoft. Hence, upgrading a server to the next supported version becomes a mandatory task for admins.

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? To answer those questions, I have listed all the server upgrade paths for Windows Server before carrying out in-place upgrades.

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Also Read: Supported SCCM In-place Upgrade Paths

Which version of Windows Server should I upgrade to?

Microsoft recommends upgrading to the latest version of Windows Server. Running the most recent version of Windows Server enables you to use the most recent features, including security enhancements, and provides the best performance.

Beginning with Windows Server 2025, you can upgrade up to four versions at a time. Meaning, you can upgrade directly to Windows Server 2025 from Windows Server 2012 R2 and later.

With Windows Server 2022 and earlier, you can upgrade to a newer version of Windows Server by up to two versions at a time. For example, Windows Server 2019 can be upgraded to Windows Server 2022 or Windows Server 2025.

Unsupported Windows Server OS

Support for Windows Server 2008 and Windows Server 2008 R2 has ended. You must update your version of Windows Server to a more recent version as soon as possible.

Related Article: Supported Windows 11 Upgrade Paths

Windows Server 2025 Upgrade Paths

Windows Server 2025 is the latest version of Windows Server available as of today. This server version can be upgraded to the next two upcoming versions of Server.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2025Upcoming version of ServerYes

Windows Server 2022 Upgrade Paths

The table below lists the upgrade paths for Windows Server version 2022.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2022Windows Server 2025Yes
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 2025Yes
Windows Server 2019Windows Server 2022Yes
Windows Server Upgrade Paths for version 2019

Windows Server 2016 Upgrade Paths

The below table lists the Windows Server upgrade paths for version 2016.

Current Windows Server VersionUpgrade to Window ServerSupported
Windows Server 2016Windows Server 2025Yes
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 2025Yes
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 2025No
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 2025No
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 2025No
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

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Prajwal Desai

Prajwal Desai is a technology expert and 10 time Dual Microsoft MVP (Most Valuable Professional) with a focus on Microsoft Intune, SCCM, Windows 365, Enterprise Mobility, and Windows. He is a renowned author, speaker, & community leader, known for sharing his expertise & knowledge through his blog, YouTube, conferences, webinars etc.