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.

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.