Windows server 2019 crashes when doing windows updates. Running on vmware 7.0.3

I have run into an issue that has been plaguing a client for many months. They are running vmware version 7.0.3. They have a compute pool that has all of their server infrastructure, mostly server 2019/2022 windows machines. For the past few months when they go to update machines, the update runs smoothly. When the update requires restart and you restart the machine, the machine crashes and we have to revert to a snapshot. We initially looked at disabling VBS and secure boot, doesn’t fix the issue. Also checked the VMX file for any abnormalities and they seem fine. This seems to be a 2019 issue as the 2022 servers seem to update fine. Has anyone dealt with this issue before? Can anyone point me in the right direction?

I am looking for a direct fix rather than an in place upgrade to 2022 as we don’t want to fix one thing and break another.

Thank you all in advanced.

Edit- I pulled a fresh 2019 iso from Microsoft and created a VM on the same network. All updates pulled from Microsoft worked. We’re thinking something is corrupted on the windows side. If anyone has any ideas, please let me know. I will update the thread with any other findings.

If licensing allows, I’d try an inplace to 2022, I doubt it will break things unless you have some odd software running on it.

Can you clone that VM and try the inplace on the clone?

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Yes, I can try an inplace upgrade to 2022. Id hate that to be the only fix, if im honest, id really like to understand what is broken here. Why would updates break a server like this?

The only time I’ve had one break this bad was outdated keys for secure boot, that was also a Server 2019 but the root cause was the keys in XCP-NG needed to be updated. When I built my production system I didn’t use secure boot on any of them to avoid the issue in the future.

Turning secure boot off didn’t change whether the machine could boot or not. As far as 2019 to 2022 goes, nothing I had got broken, even my Trellix ePO server continued to work. Never had an issue from 2008 all the way up to 2019 on my AD servers either, the inplace generally just worked. Maybe I’m lucky, but I also try to keep my servers extremely vanilla whenever possible.

What services is this 2019 running? Anything non-microsoft? Just wondering if MS updated something, and a non-MS application is hanging after the update. I can’t see a driver doing this, but maybe check the VMware drivers for updates before doing the 2019 monthly update that is killing it.

In testing I spun up a brand new 2019 server. No services, just bare bones. Still wasnt able to download updates from MS and reboot without crashing. Strange stuff…

That is strange, especially since 2019 is supported for a few more years.

What happens if you inplace upgrade that test server to 2022? It might crash as well once the updates get applied.

Going to test this and will update the thread.

If it were me I would open up CMD as admin and run
DISM /Online /Cleanup-Image /RestoreHealth