Share via

In-Place Upgrade for Server 2025 Azure Edition

Eigenmann René 6 Reputation points
2025-09-04T10:11:15.7566667+00:00

Has anyone ever tried an in-place upgrade of a windows server azure edition?

I have a Windows Server 2022 Azure Edition Virtual Machine that I would like to upgrade to Server 2025. If I add the ISO of Server 2025 as a disk to the server the "Keep files, settings, and apps" option is always greyed out.

I guess it could be a problem because I can't choose Server 2025 Azure Edition but I did not find any documentation on how to get the installation files for that.

Any help would be greatly apreciated

Azure Virtual Machines
Azure Virtual Machines

An Azure service that is used to provision Windows and Linux virtual machines.

Answer recommended by moderator
  1. Ankit Yadav 13,135 Reputation points Microsoft External Staff Moderator
    2025-09-06T00:58:44.1+00:00

    Hello @Eigenmann René ,

    The option to "Keep files, settings, and apps" option being greyed out is expected when you are trying to upgrade to Windows Server 2025 Datacenter Azure Edition. The reason behind is due to Azure Edition not supported in the official in-place upgrade path from Microsoft (see officially supported path: Windows in-place upgrade - Azure Virtual Machines | Microsoft Learn) as discussed in earlier threads: https://dotnet.territoriali.olinfo.it/en-us/answers/questions/5530340/how-to-upgrade-windows-server-2022-datacenter-edit

    At this point, if you are looking for the in-place Windows upgrade to Windows Server 2025 Datacenter Azure Edition, you'd have to unfortunately wait until it gets listed in the supported path

    and

    if you are planning to migrate now recommended steps can be as below:

    1. Back Up Your Data: First, please ensure you create a full backup of all your files, applications, and system data. You can copy this to a managed Azure disk or an Azure Blob Storage container for safety (for reference, see: Azure Managed Disks Overview, Introduction to Azure Blob Storage).
    2. Perform a Clean Installation: Deploy a new virtual machine running Windows Server 2025 Datacenter (for reference, see: Windows Server 2025 Installation Guide).
    3. Restore Your Data: Once the new OS is installed and configured, you can then restore your files and reinstall your applications from the backup you created

    1 person found this answer helpful.

1 additional answer

Sort by: Most helpful
Most helpful Newest Oldest
  1. Michele Ariis 7,210 Reputation points MVP Volunteer Moderator
    2025-09-04T12:29:12.3333333+00:00

    Hi, you used the wrong media. “Keep files, settings, and apps” is greyed out because you’re trying to upgrade Windows Server 2022 Datacenter: Azure Edition with a generic Server 2025 ISO (different SKU). Use the Azure upgrade media instead: create the managed disk from the hidden Marketplace offer MicrosoftWindowsServer/WindowsServerUpgrade with SKU server2025Upgrade, attach it to the VM, then run on the VM: .\setup.exe /auto upgrade /dynamicupdate disable /eula accept and choose Windows Server 2025 Datacenter: Azure Edition when prompted. Make sure you run setup from inside the OS (not boot), the VM is on Managed Disks, has enough free space, and the system/locale is en-US (upgrade media is en-US only). Note: the Azure portal won’t change the “image/plan” after the upgrade, only the OS inside the VM changes. If the Azure Edition 2025 target doesn’t show up in the selector, that path isn’t available in your region/tenant yet, deploy a new WS 2025 Datacenter: Azure Edition VM and migrate (swap OS disk/ASR) instead.

    0 comments

Your answer

Answers can be marked as 'Accepted' by the question author and 'Recommended' by moderators, which helps users know the answer solved the author's problem.