How to perform In-Place upgrade from Azure VM 2008R2 to Server 2019

Question

We are migrating On-premises Windows Server 2008 R2 to Azure via Rehost approach. Post migration, we want to upgrade to the server 2019 OS. Direct upgradation from 2008R2 to 2019 it's not possible, then what would be the solution.

Answer 1

@Mahavir Saroj Thank you for posting your question on Microsoft Q&A platform. Happy to assist!

From the tile of the post, I understand that you want to migrate your on-premises Windows Server 2008 Rs to Azure and post migration upgrade it to Windows Server 2019. I see that you are aware that direct upgradation from Windows Server 2008 R2 to Windows Server 2019 is not possible as per MS documentation - https://learn.microsoft.com/en-us/azure/migrate/how-to-upgrade-windows

IMO, you can upgrade from Windows Server 2008 R2 to Windows Server 2012 post migration and then follow this approach - https://learn.microsoft.com/en-us/azure/virtual-machines/windows-in-place-upgrade#perform-in-place-upgrade-to-windows-server-2016-2019-or-2022 to upgrade from Windows Server 2012 to Windows Server 2019.

I'm checking with Azure Migrate team to get a confirmation on following the mentioned approach as a workaround to meet your requirement.

Thanks for your understanding!

Update:

Azure Migrate team confirmed that as of now there are no plans to support direct upgradation of OS (In you case - Windows Server 2008R2 to Windows Server 2019)

The current workaround would be to follow the approach mentioned in the screenshot below:

Hope this answers your question. Please reply if you have any further questions in this matter!

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