Windows Server 2019 Upgrade Paths

This post lists the Windows Server 2019 upgrade paths. If you are looking to perform an in-place upgrade of your existing server to Windows Server 2019, upgrade paths are important.

Windows Server 2019 is the latest server operating system by Microsoft. I have worked on both Server 2016 and Server 2019 and I love Windows Server 2019. So far I have not encountered any major issues while working on it.

Most organizations today look to upgrade their server OS to 2019 because it offers more features than existing server versions. To know what’s new in Windows Server 2019, read this article.

Some of the best features of Windows Server 2019 include.

  • Windows Admin Center.
  • Desktop Experience
  • System Insights
  • Hybrid Cloud
  • Security

Note – Extended support for Windows Server 2008 R2 and Windows Server 2008 ends in January 2020.

Windows Server 2019 Upgrade Paths

You can perform direct in-place upgrade to Windows Server 2019 from either of these server OS :-

  • Windows Server 2012 R2
  • Windows Server 2016

In order make it easier to understand, I have listed the upgrade paths in a table. One thing remember is prior to Windows Server 2012 R2, no other server OS supports a “direct” in-place upgrade to Windows Server 2019.

Windows Server OS Upgrade To Upgrade Paths
Windows Server 2008 R2 Server 2019
  1. First upgrade to Windows Server 2012
  2. Upgrade Server 2012 to Server 2016
  3. Upgrade from 2016 to 2019
Windows Server 2012 Sever 2019
  1. Upgrade to Windows Server 2016
  2. Direct upgrade from 2016 to 2019
Windows Server 2012 R2 Server 2019 Direct upgrade supported
Windows Server 2016 Server 2019 Direct upgrade supported


Here is the Windows Server In-Place upgrade information by Microsoft. If you notice the down arrow, that should tell you the upgrade paths to Server 2019. The screenshot also lists the Mainstream support period and Extended support period for every Server OS.

Windows Server 2019 upgrade paths
Copyright Microsoft – Windows Server upgrade paths


Hi, I am Pragati. As a Technical Consultant, I help businesses harness the latest innovations in Cloud applications, Intune, Windows 365, and more. Sharing my knowledge and insights through this blog to inspire and empower others in their digital transformation. Let's revolutionize the way we work and thrive in the cloud era together!

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