In-place upgrade from Windows Server 2012 r2 to Windows Server 2019

Question

We want to upgrade our production server from Windows Server 2012r2 to Windows Server 2019.
We are a little concerned of doing an in-place upgrade. Does anybody have an issue with it or have any suggestion?

Or should we try to spin up a Hyper-V on this server and then upgrade the Hyper-V to Windows 2019?

Before we spin up the Hyper-V, do we have an option to select Windows 2019 to install or the Windows Server 2012r2 has to be installed first since the host is on Windows 2012rs?

Thanks,

Tee

Answer 1

I recommend doing in-place upgrades if the system itself is SOLID and does not have any issues.

https://www.ajtek.ca/wsus/another-successful-in-place-upgrade-why-not-change-how-you-think/

I've upgraded 2012>2012R2>2019>2022 all in-place and 99% have been without issue each time. The 1 system that had an issue - I used setupdiag to tell me what was going wrong - ended up being a Windows Feature for RRAS management (not the services, the GUI Management), so I removed it, in-place upgraded, and then added it back in.

Answer 2

Did you encounter problems when moving the VMs from the 2012 R2 server to 2019?

In my case VMs which did not have checkpoints were successfully moved over to the new hardware running Windows 2019. The configuration version was upgraded and everything worked fine.

The VMs which have checkpoints were also successfully moved to the new server but after I upgraded the configuration version from 5.0 to 9.0 the checkpoints were split into additional VMs instead of being nested under the original VMs.