Hello team,
My team and I are encountering an issue when attempting an in-place upgrade on a Windows Server 2019 machine. After several failed attempts, we discovered that this is a physical server, not a virtual machine.
We’ve successfully completed multiple in-place upgrades using OSD on virtual machines (as it turns out, all our previous upgrades have been on VMs), but we’re unable to upgrade this specific physical server.
Has anyone experienced a similar issue, or have any insights on this?
There aren’t any specific requirements, other than of course the machine must support the new operating system.
I’d check the Windows Setup logs. They’re listed at Log files that are created when you upgrade to a new version of Windows - Microsoft Support
In particular C:\Windows\Panther\Setupact.log and C:\Windows\panther\setuperr.log will usually show if there’s a problem.
I can’t say I’ve seen any particular issues with 2019 to 2022, but I honestly haven’t done that many of them (I stuck with 2016 for a long while). In previous Windows upgrades though a couple of common things I saw was where hardware driver support was not provided in the newer OS, or where some Windows components were not present in the new version so Windows would block the upgrade. I think ‘Miracast’ is triggering a memory on that one.
In any case, one of the logs listed in the article should help determine where it’s going wrong.