In-Place Upgrade from Windows Server 2016 to 2019/2022 Stuck at 32%

Question

Hello,

I have been attempting to run an in-place upgrade from our Windows Server 2016 Datacenter Azure VM to Windows Server 2022 Datacenter (following the instructions here)

Every attempt gets stuck at 32% progress. I have tried upgrading to Server 2019 first, and the same behavior occurs.

There is 200 GB+ free space on the OS drive. All third-party antivirus has been uninstalled/disabled. The VM has volume licensing/Azure Hybrid Benefit enabled. I have tried running updates, cleanmgr, and SFC/DISM before attempting the upgrade.

At this point I am starting to accept that I may just need to create a fresh VM and start from scratch, but would REALLY rather not as this server has a lot of apps to reinstall with various license/product keys and I can't guarantee I'll be able to get all of the apps they need reinstalled for them on a fresh VM.

Thanks,
AM

Answer 1

Hello,

Since you’ve already taken steps, such as ensuring there’s enough free space, disabling antivirus software, and performing system maintenance, there are a few additional troubleshooting steps you could try:

1、Check the Windows Event Viewer logs (Setup, System, and Application logs) for any errors or warnings that might provide more context about why the upgrade is getting stuck. Look specifically for entries around the time the upgrade begins and when it reaches 32%.

2、Instead of using an in-place upgrade through Windows Update, consider creating a bootable USB or DVD with the Windows Server 2022 ISO image and perform the upgrade using this media. This method can sometimes resolve issues related to the upgrade process.

3、Ensure that the VM has sufficient resources, especially memory and CPU. Sometimes, the upgrade process can fail due to insufficient resources.

Best Regards,

Hania Lian

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Answer 2

Hi SP RA,

Welcome to the Microsoft Q&A Platform! Thank you for asking your question here.

We understand from your query that you are experiencing an issue while trying to upgrade windows server 2016 to windows 2019/2022. I have shared troubleshooting steps that I felt will help resolve the issue you reported.

Run SetupDiag, a diagnostic tool from Microsoft that examines Windows setup log files to identify common issues. It may help identify the specific component or process responsible for the hang. Download the file and run it. For detailed information visit https://learn.microsoft.com/en-us/windows/deployment/upgrade/setupdiag

Even if you have sufficient space, temporarily increasing the OS disk size can sometimes facilitate the upgrade process. You can expand it and then revert to the original size once the upgrade is finished.

If the in-place upgrade continues to fail, consider capturing an image of your VM, then attach an OS disk of the target version to preserve your applications and configurations.

Please let us know if you have any further queries. I’m happy to assist you further. If the answer is helpful, please click "Accept Answer" and "Upvote it" as it can be helpful to others in the community.