server upgrade from 2019 to 2022

Good morning, I wanted to ask why if I try to update from Windows Server 2019 to Windows Server 2022 it doesn't let me keep my settings and files, the update setting remains gray but it just makes me install the operating system from scratch, deleting everything.

Being a server in production I would like to test on a server installed with server 2019 server and update it to server 2022.

Thank you

I had the same issue, I updated using Window Server 2022 Datacenter. It worked for me. If you have window server data center installed and you try updating using Standard version then it will not let you keep the files and setting and option will be greyed out.

Hello,

First of all. Make sure your computer:

• Make sure you have a valid product key and activation method. Keys and methods may vary depending on the distribution channel you received Windows Server media from, for example a Commercial Licensing program, Retail, or Original Equipment Manufacturer (OEM).
• Ensure that the install media is ready to use.
• Have a location to store files away from your computer, such as a USB flash drive or network location.
• Review Upgrade and migrate roles and features in Windows Server.
• Review Microsoft server applications compatibility.
• Review any third-party application vendor support requirements.
• Make sure your computer:
  • Meets or exceeds the hardware requirements for Windows Server.
  • Isn't running in Azure.

To perform an in-place upgrade from Windows Server 2019 to Windows Server 2022, follow these steps:

1. Using File Explorer, navigate to the Windows Server Setup media. Then open setup.exe.
2. By default, setup automatically downloads updates for the installation. If you're okay with the default settings, select Next to continue.
   If you don't want Setup to automatically download updates, select Change how Setup downloads updates, choose the option appropriate to your environment, and then select Next.
3. If prompted, enter your product key and then select Next.
4. Select the edition of Windows Server you want to install and then select Next.
5. Review the applicable notices and license terms. If you agree to the terms, select Accept.
6. Select Keep personal files and apps to choose to do an in-place upgrade, and then select Next.
7. After Setup finishes analyzing your device, it displays the Ready to install screen. To continue the upgrade, select Install.

The in-place upgrade starts, and you should see a progress bar. After the upgrade finishes, your server restarts.

More details please refer to this link: Perform an in-place upgrade of Windows Server | Microsoft Learn

Note: Before performing the upgrade, it is recommended to take a backup of your important data and create a system restore point.

Best Regards,

Hania Lian

Thanks for the information, This answer is helpful to me.

I am glad that I was able to help you solve this problem. To help other customers who may be facing the same issue, please vote yes or no.

Best Regards,

Hania Lian