I have been holding back to upgrade the operating system for all of the Windows 2016 Servers in my lab to 2019 due to lack of support of it in SCVMM 2016. But because recently SCVMM 2019 has been released. So I am gonna upgrade all of the servers to 2019 using in-place upgrade.

The article today is mainly to perform an in-place upgrade for Windows Server 2016 to Windows Server 2019. Before that a few things..

a) The system I am working on is a VM running Windows Server CORE 2016 (Upgrade process is the same for both core and Desktop Editions)
b) Upgrade methods are based on my own trial and error and my differ from others.
c) If the system you are upgrading is a production server, PERFORM A BACKUP before proceeding

Let's Start..

1) Insert Disc or ISO to Server
2) Login to the server and navigate to the Disc drive (in my case D:)
3) Run Setup.exe

4) Select the necessary options, click Next

5) Enter Product key, click Next
Note : If you are using AVMA keys.
You will receive an error "This Key doesn't work with this edition of Windows. Try a different key."

You need to use the published KMS keys to do the upgrade. After the upgrade you can then use the AVMA keys to activate against a Datacenter host.

KMS Key Information : https://docs.microsoft.com/en-us/windows-server/get-started/kmsclientkeys

AVMA Key Information : https://docs.microsoft.com/en-us/windows-server/get-started-19/vm-activation-19

6) Select the Edition you want to upgrade to (in this case without Desktop Experience), click Next

7) Click Accept

8) Choose the options you wish to use.
Note : Selecting Nothing will be similar to a full format.

9) Click Install

10) You can leave it running and continue doing other things if you need to

Once the server restarts. The upgrade is completed!

Have fun with Windows Server 2019!