@Komendat Jason
Hi,
If in place upgrade really didn’t work as you said, may you provide info about the distinctions (version, drivers or settings, etc.) between the failed and the succeeded VMs so that we can do further research.
you can compare your procedure with the following links to find differences
https://learn.microsoft.com/en-us/windows-server/upgrade/upgrade-2012r2-to-2019
Based on my knowledge. In place upgrade from 2012 to 2019 is not supported, rather we can do in-place upgrade from 2012 R2 to 2019, perhaps you omit R2 in your description.
Overview of Windows Server upgrades.
https://learn.microsoft.com/en-us/windows-server/upgrade/upgrade-overview
Otherwise, usually we advocate clients to do clean install, upgrading their servers to latest version. Back up data first and migrate back to new server 2019 which is the most efficient method.
You can refer to the following links for details.
https://learn.microsoft.com/en-us/windows-server/get-started-19/install-upgrade-migrate-19
Hope above information can help you.
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