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Supportability Query: In-Place OS Upgrade of ASR Configuration Server from Windows Server 2016 to 2019

Ronak Naresh Joshi 0 Reputation points
2026-05-26T05:54:07.76+00:00

Supportability Query: In-Place OS Upgrade of ASR Configuration Server from Windows Server 2016 to 2019

Dear Microsoft Support Team,

I am writing to seek clarification on the supportability of performing an in-place operating system upgrade on an Azure Site Recovery (ASR) Configuration Server, specifically from Windows Server 2016 to Windows Server 2019.

Our Environment:

  • ASR Configuration Server (Classic/VMware architecture) currently running Windows Server 2016
  • Actively replicating servers to Azure, including Windows Server 2008 / 2008 R2 machines
  • Using the classic ASR architecture (not the modernized replication appliance)

What We Are Trying to Achieve:

We are aware that Windows Server 2016 is approaching end of support and wish to upgrade the underlying OS of our configuration server to Windows Server 2019 without having to deploy a brand new appliance and re-register all protected machines.

Our Specific Questions:

  1. Is an in-place OS upgrade from Windows Server 2016 to Windows Server 2019 supported or tested on an ASR configuration server?
  2. Will the ASR services, vault registration, and replication policies survive an in-place OS upgrade, or will they need to be reconfigured afterwards?
  3. Will replication of our Windows Server 2008 / 2008 R2 source machines be impacted or interrupted during and after the upgrade?
  4. If an in-place upgrade is not supported, what is the recommended migration path to get the configuration server onto a newer OS while minimising downtime to replications?

We have reviewed the public support matrix documentation and the replication appliance support matrix; however, we could not find explicit guidance covering this specific scenario for the classic configuration server on Windows Server 2016.

We would appreciate a clear supportability statement so we can plan this change with confidence.

Thank you for your assistance.

Kind regards,

Ronak

Windows for business | Windows Server | Devices and deployment | Set up, install, or upgrade
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  1. Scott Nguyen 1,470 Reputation points Independent Advisor
    2026-05-26T07:27:44.78+00:00

    Hello Ronak,

    Unfortunately, I would say performing an in-place OS upgrade on a classic ASR Configuration Server to Windows Server 2019 is unsupported by Microsoft and most likely will break the integrated application components, including the local MySQL database and the registration keys.

    Because of this, your ASR services would not survive the upgrade, and replication for your Windows Server 2008 and 2008 R2 workloads would also fail, forcing a complete and manual reconfiguration. Furthermore, the classic configuration server architecture officially only supports up to Windows Server 2016, so you cannot run the legacy components on a newer OS regardless of the deployment method.

    To achieve the upgrade, I recommend to deploy a brand-new ASR Modernized Replication Appliance, which natively runs on Windows Server 2022. Once the new appliance is registered, you can use the built-in migration feature within your Recovery Services vault to transition your existing items from the classic server to the modern appliance.

    Still, I know this sounds like a lot of work, but it would minimize replication downtime and skip some steps involved in manually re-registering the legacy mobility agents.

    Best regards,

    Scott

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