Business Scenario:

Consider a scenario where one or all the customer’s VMs are running on Windows Server/Client OS, which is the end of support from Microsoft, and OS upgrade is not supported through update and management tool.


Challenges:

  • Microsoft announced the end of support for Windows OS like Windows XP, Windows 7, and Windows Server 2008 long ago.
  • Many customers’ client and server systems are still running on these OS on the Azure cloud.
  • There are some complex application setups where the agent is installed on a client OS like windows 7, and the Management engine is on Server OS like Windows Server 2008, which is the end of support.
  • Some complex applications are configured and hosted only on the server running on Server OS, which is the end of support from the Microsoft side.
  • Due to code complexity or business revenue from any such application, it’s risky to deploy a new setup on the latest supported version of OS on new VMs.
  • There is also a risk of keeping these application setups running on an unsupported version of OS as its vulnerable to new threats.
  • As of Jan 2023, Microsoft doesn’t have any OOB tool to perform the in-place upgrade for an unsupported OS running on the Azure cloud.

Solution Strategy:

  • Take a backup of VM configurations like NIC, IP, data discs, NSG rules, LAW connection, and more.
  • Ensure complete and latest VM backup is in place.
  • Download the Operating System VHD of the VM in the scope of OS upgrade to an isolated environment.
  • Install the Hyper V feature and connect this VHD to have a VM running on an isolated hyper environment.
  • Download the iso of the latest supported version of the OS you wish to proceed with.
  • Attach this iso to the virtual drive and perform an in-place upgrade.
  • Activate the OS by entering a valid license key.
  • Check the application functionality in an isolated environment.
  • Upload this VHD to Azure and spin a new VM.
  • Check the application functionality in the Azure environment.
  • Stop and deallocate the old VM by approving application downtime from business owners.• Stop and deallocate the old VM by approving application downtime from business owners.
  • Update configuration of new VM as per backup taken for NIC, IP, data discs, NSG rules, and LAW connection.
  • Check the application functionality in production.
  • Delete the old VM and associated resources.

How to upgrade Azure VMs for unsupported OS


Outcome & Benefits:

  • Minimum application downtime.
  • Minimize risk in terms of security and application functionality.
  • Get support from Microsoft as they have moved to a supported version of OS.
  • Enhanced application performance on the latest platform with additional security features.
Pranav Thombre

Pranav Thombre

Operations Manager (Azure Cloud) - Managed Services

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