Fail on In-place Upgrade to Windows Server 2019

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New 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. 

https://docs.microsoft.com/en-us/windows-server/upgrade/upgrade-overview

Some people do recommend it.

I was just trying it out. 

 

 

Sounds good, now you know why.