I've been assigned to upgrade some servers from Windows Server 2012 R2 to 2016 in an in-place manner, even though I know it's generally not recommended. I've successfully upgraded from 2016 to newer versions before, but this time I'm hitting some major roadblocks. After two failed attempts, I'm encountering issues like Configuration Manager not showing any data, SCCM and Software Center failing to open, and errors related to 'CDPUserSvc_##### has stopped working.' I'm also experiencing Remote Desktop Protocol (RDP) problems, which might just stem from my inability to apply patches post-upgrade. Any tips on how to resolve these issues would be greatly appreciated!
7 Answers
You could consider using services like cloudhouse.com, though I haven't personally tried it yet, so I'm unsure about the costs.
One issue you might be facing is related to WMF 5.1 being present during your upgrade. It can really break WMI afterwards, so it’s a good idea to remove it before you start the upgrade. I posted some detailed tips on this on my blog last year.
Is it absolutely necessary to upgrade to 2016? I’ve done around 80 upgrades from 2012 R2 to 2019 without any issues whatsoever. Clean installs for AD servers, but the rest were in-place.
I've done many upgrades using snapshots as a safety net—if things go awry during the process, just roll back to the snapshot!
If you're running into persistent issues, I would suggest pushing back and advocating for a clean install instead of an in-place upgrade. Especially since 2016 isn't supported anymore, why not transition to a newer version? You could mention allowing the team to tackle this on their own if they doubt your advice; it could showcase how serious the situation is. However, if you're handcuffed by application requirements, just keep looking for solutions until you can escalate.
It might help to install .NET 4.8 while addressing these issues. I remember doing that in the past to fix some underlying problems, so it’s definitely worth a try!
Upgrading from 2012 R2 to 2016 can often lead to complications. I've run into similar situations where SCCM or Software Center breaks after such an upgrade. In my experience, it usually boils down to issues with WMI or the SCCM client being corrupted. I found that completely uninstalling and reinstalling the ConfigMgr client can sometimes resolve the chaos. Also, it's worth repairing or installing .NET 4.8 since it has addressed random crashes for me post-upgrade. Lastly, the CDPUserSvc_ errors might go away after you fully patch and reboot the server a few times. And don't be surprised if RDP gives you trouble right after the upgrade; that typically smooths out once everything is updated and the drivers are sorted out.

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