Hi Clint.
I believe that you are reading more into the statement than it actually entails.
As you know, ITMS 8,1 is no longer supported. In addition, ITMS 8.1 never supported Windows Server 2022 or SQL Server 2022. Support for those technologies was added to ITMS after ITMS 8.1 was EOL'd.
Whether you could first upgrade ITMS to a more recent version that supports your current version of WIndows Server and SQL Server and later upgrade Windows Server and SQL Server to newer versions is a different question.
Our statement is not intended to convey that there have been some magic new developments that support in-place upgrades from any version of Windows Server to any other version, or from any version of SQL Server to any other version. I doubt that Microsoft would even go that far.
The statement indicates that limited testing of in-place upgrades was performed and that no critical issues were identified. Testing was performed in scenarios such as the following:
- Windows 2012 R2 Server to Windows 2016 Server
- Windows 2012 R2 Server OS to Windows 2016 Server and then from Windows 2016 Server to Windows 2022 Server
- Windows 2016 Server to Windows 2022 Server
- Windows 2019 Server to Windows 2022 Server
No testing was performed using versions of these products that are no longer supported by Microsoft.
The statement does not guarantee that you will be able to successfully perform an in-place upgrade. It implies that such upgrades are not strictly prohibited and can be successfully performed. However, it advises customers to take precautions necessary to maintain or be able t restore their production environment.
It's unlikely that you're going to find that it's easy (or even possible) to directly upgrade from versions of Windows Server and SQL Server that are several generations old to the latest versions. Our statement does not indicate you will be successful in that regard.
I would strong advise you to consider other alternatives to a single-step, in-place upgrade from such old versions of these technologies. You may want to explore a multi-step process or do an off-box migration. Whatever approach you choose, please take the precautions necessary.