This question is two fold however I know the answer to one of them the question comes down to the order in which I do this as two operations have to happen here and I'm just looking to see what some think the best practice would be.
I have a Windows Server 2008 R2 physical server and it's a DC, I'm planning for in-place upgrades to Server 2019. The question I have is should I convert the 2008 R2 server first to a VM before doing in-place Windows Server upgrades, or get my upgrades done on the physical and then convert to a VM. What are in-place upgrades like on a VM? As I've never done them before.
Moderator: Moved to Virtual Machine, Guest OS & VM Tools > Windows
If it's a domain controller, neither. The recommendation would be to deploy a new VM and replicate with your physical server. Once everything is replicated, simply decommission your physical server and be done with it.