Windows 2003 Server on Azure

Tim Chapman 6 Reputation points Microsoft Employee
2022-09-27T05:19:42.99+00:00

Hi Team,

Looking for guidance on moving Windows Server 2003 workloads to Azure. We have successfully migrated a single Windows 2003 Server (64bit) but have run into a few other issues.

  • Repeatable migration process for Windows 2003 (64 and 32bit) servers from VMWare and Physical servers on premise. (We have been migrating Windows 2008 R2 / Windows 2012 / Windows 2016 using Azure Migrate over the last year or so)
  • How to configure / manage infrastructure services like connecting the VM to an existing AD Domain. (At the moment we have Windows 2019 DC’s in Azure and Windows 2012 DC’s On Premise. For reference SMBv1 is disabled in Azure. This is likely due to the functional level of the domain controller being higher than 2003.
  • Tools we could use on premise to determine the dependencies, noting the Azure Migrate agent is not supported on Server 2003. Are there any suggestions for agentless or prior dependency mapping tools you would recommend? eg prior version of Microsoft Assessment and Planning Toolkit
  • Monitoring capabilities post migration in Azure, what options do we have.
  • How shall we achieve DR for these servers. Are offline snapshots the only backup / DR option?
    • Security: what is the recommended approach for ringfencing and securing these workloads on the assumption they are out of support and insecure.

Thanks,
Tim

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  1. Ravi Bakamwar 11 Reputation points
    2022-10-04T02:34:47.007+00:00

    Hi Tim,

    Here are few notes based on what discussed during FTA Live QnA session.

    • Azure Migrate is capable of migrating/replicating Windows Server 2003 running on Hyper-V/Vmware (both 32/64 bit) provided Hyper-V integration Services has been installed (for the VM to be able to boot after it is migrated to Azure). There is no support for physical but P2V VHD upload might work.
    • As discussed, you could explore create a dedicated vnet with Windows 2021 DCs and configure AD Sites and Services/Subnet to map Windows 2003 Servers to this new AD "site"
    • Older MAP tool might be able to help.
    • Native capabilities can be used since Windows Server 2003 VMs do not support any agent/extension. Would need to use classic OS level approach (such as perfmon)
    • Windows Backup (OS Level).
    • Azure Network constructs such as vnet/NSGs.
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