An Azure native disaster recovery service. Previously known as Microsoft Azure Hyper-V Recovery Manager.
Thanks for raising this question.
Based on the current Microsoft guidance, an in-place operating system upgrade is supported for Azure virtual machines, provided the source and target Windows Server versions are supported by the in-place upgrade matrix and the VM meets the documented prerequisites. However, whether the VM is a member of a Virtual Machine Scale Set (VMSS) using Flexible orchestration is an important consideration.
If the VM has effectively been modernized and is now managed as an individual VM within a Flexible orchestration scale set, the OS upgrade itself is performed on the VM rather than on the scale set. Before proceeding, I would recommend:
- Taking a full backup or creating a restore point/snapshot.
- Verifying that the VM uses a supported marketplace image and Windows Server upgrade path.
- Confirming that any VM extensions, monitoring agents, and security software are compatible with the target OS version.
- Validating that your application supports the target operating system.
For production workloads, it's also worth considering whether a side-by-side deployment (building a new VM with the target OS and migrating the workload) would provide lower risk and an easier rollback strategy.
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