How to upgrade Azure VMs for unsupported OS - Cambay Consulting | Cloud Infrastructure

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.