Deprecation notice: Migrate to new Microsoft Marketplace Windows Server 2022 images by 9 June 2026

Azure VMs don’t support in-place OS image upgrades. To move from deprecated Windows Server 2022 Marketplace images to a supported offer/SKU with minimal downtime, a side-by-side migration is required. Downtime is limited to the cutover when switching to the new VM(s).

High-level approach for each VM (AD and standalone app VM):

1. Check if the current image has a purchase plan
   This determines how urgent migration is and what breaks after enforcement.
   • Use Azure CLI or PowerShell as described in “How do I check if my image has a purchase plan?”.
   • If the command returns null, the image has no purchase plan (Microsoft first-party). Existing VMs keep running; main impact is on reimage/new VM creation and VMSS scale-out.
2. Plan for side-by-side migration (no in-place OS upgrade)
   From “How do I migrate a VM to a different image?”: Azure VMs don’t support in-place OS upgrades. The supported path is:
   • Create a new VM from a supported Windows Server 2022 (or later) image.
   • Migrate roles/data/configuration.
   • Cut over traffic/users.
   • Decommission the old VM.
3. Create new VMs with supported images (via Azure portal)
   For each existing VM:
   • In Azure portal, go to Virtual machines → Create → Azure virtual machine.
   • In the Basics tab, select the same subscription, resource group, and region as the existing VM.
   • Under Image, choose a non-deprecated Windows Server 2022 image (or newer) from Marketplace.
   • Choose a VM size comparable to the current VM.
   • Configure OS disk, networking, and availability options to match the existing VM as closely as possible.
   • Complete Management, Monitoring, Advanced, and Tags to mirror the current configuration.
   • Create the VM.
4. Migrate the AD VM with minimal downtime
   For the AD domain controller VM:
   • Join the new Windows VM to the existing domain.
   • Promote it to an additional domain controller (install AD DS, run dcpromo/Server Manager wizard).
   • Allow replication to complete and verify AD health.
   • Transfer/seize FSMO roles if needed.
   • Once stable, demote the old domain controller and shut it down.
   • Downtime is limited to brief DNS/AD failover, if any, during cutover.
5. Migrate the standalone application VM with minimal downtime
   For the standalone app VM:
   • Install required runtimes (for example, .NET 6+ or newer supported version) and prerequisites on the new VM.
   • Copy application binaries/configuration and data (for example, via file copy, backup/restore, or application-specific migration tools).
   • Configure IIS or other web/app server identically (sites, bindings, certificates, etc.).
   • Test the application on the new VM using its private IP or a test DNS name.
   • During a short maintenance window:
     • Update DNS records, load balancer backend pool, or other routing to point to the new VM.
     • Stop the application on the old VM.
   • This keeps downtime to the DNS or routing switch interval.
6. Use Azure Compute Gallery for future resilience (optional)
   To avoid future Marketplace deprecation impact:
   • After building and hardening the new VMs, capture them as custom images in Azure Compute Gallery.
   • Custom images aren’t subject to Marketplace deprecation.
7. Understand what happens if the image is already enforced
   From the deprecation behavior:
   • Existing VMs continue to run normally after enforcement.
   • New VM creation from the deprecated image and reimage are blocked.
   • For images without a purchase plan, backup/restore and ASR continue to work; for images with a purchase plan, restore might fail.
   • Because in-place OS upgrade isn’t supported, the side-by-side approach above is the supported way to move to a new offer/SKU with only a brief cutover window.

This approach satisfies the requirement of avoiding long downtime while moving to a supported Windows Server offer/SKU and away from deprecated images.

References:

• Deprecated images FAQ