Part 2 – How to Upgrade Windows Server 2016 to Server 2019 or 2022

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In this blog, we will upgrade a Windows Server 2016 R2 standard to Windows Server 2019 standard.

Windows Server Upgrade Matrix

The inplace upgrade service permits us to handle upgrades to newer versions within a short window. You can use the following diagram to figure out which Windows Server version you can upgrade to, based on the version you’re currently on:

Available in-place upgrade paths

We will attempt to migrate our Windows 2016 server running on datacenter version to 2019.

How to Upgrade to Windows Server 2019

Snapshot the virtual machine


Mount the Windows 2019 ISO and then click on setup

Locate the Windows Server 2019 Setup media, and then select setup.exe.

Choose download and install updates and click Next to continue

Select the Server edition with the desktop experience option if GUI is needed and then click next.

Accept End user license

Select Keep personal files and apps to choose to do an in-place upgrade, and then select Next.

keep personal files and apps

Click Next to continue

making sure ready to install

Click on install to begin the install process.

Installing Windows Server 2019.

Windows Server 2016 has been upgraded

Make sure all of your applications are running and that your client connections to the applications are successful.

References

Windows Server Documentation

Windows Server 2016 to 2019 Upgrade

Converting Eval to Retail Version

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By C A Thomas

Chinchu A. Thomas is an Infrastructure Analyst specializing in Microsoft Azure, the Microsoft 365 suite, AWS, and Windows infrastructure management products.

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