Fail on In-place Upgrade to Windows Server 2019

Copper Contributor

I have a Windows Server 2016 desktop experience VM I want to in-place upgrade to Windows Server 2019 DE. I get to where the upgrade starts then after bit it fails with no error. Just a square that says "windows server 2019 upgrade has failed." No error.  I checked what i thought were the correct logs but couldn't find any errors. Would something be in the event viewer?

3 Replies

In-place upgrades are never recommended and can be problematic for any number of reasons. You'll find the setup log locations listed here. Always better to stand up a new one, patch fully, migrate roles over.

Windows setup log file locations - Windows Client | Microsoft Docs



This is a test server.

Microsoft states is a legitimate upgrade option.

Some people do recommend it.

I was just trying it out. 



Sounds good, now you know why.