Hi @Ralton Leendertz
Thank You for posting in Q & A.
You should follow two step upgrade process Windows Server 2008 to Win 2012 and then Win 2012 to Win 2016.
Upgrade path
You can directly do an in-place upgrade to Windows Server 2019 from Windows Server 2016 and Windows Server 2012 R2. This means, to upgrade from Windows Server 2008 R2 to Windows Server 2019
you will have two consecutive upgrade processes.
First, you upgrade Windows Server 2008 R2 to Windows Server 2012 R2
Secondly, you will upgrade Windows Server 2012 R2 to Windows Server 2019
https://techcommunity.microsoft.com/t5/itops-talk-blog/how-to-in-place-upgrade-windows-server-2008-r2-to-windows-server/ba-p/752330
In general, there are 2 ways for system upgrading:
- In-place upgrade
- Migration
Windows Server installation and upgrade
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