Hello @JB Thank you for reaching out to us on Microsoft Q&A platform. Happy to help!
Based on the information shared, I understand that you want to migrate your on-premises Windows Server 2012 to Azure and upgrade the OS to Windows Server 2019. However, you encountered an error during the test migration.
Note: Direct upgrade from Windows Server 2012 to Windows Server 2019 is not possible as per MS documentation - https://learn.microsoft.com/en-us/azure/migrate/how-to-upgrade-windows
Recommended workaround: IMO, you can upgrade from Windows Server 2012 to Windows Server 2016 and then post migration 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 2016 to Windows Server 2019.
Hope this helps resolve your issue. Please write back to us if you need any further assistance in this matter!
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