I have a requirement to upgrade one of our Operating Systems from Windows Server 2012R2 to Windows Server 2016. The hosted application requires numerous ODBC Drivers that in turn require a bunch of Microsoft Redistributables. My problem is that several of the redistributable packages are not listed as supported for Windows Server 2016.
We also need to install Cloudera Impala ODBC driver which according to the documentation is compatible with Windows Server 2016, however the documentation also tells us the driver needs Visual C++ Redistributable Packages for Visual Studio 2013 which according to Microsoft is not supported on Windows Server 2016.
We also require SQL Server ODBC Driver 17 and this is listed as Windows Server 2016 supported, so it looks like Microsoft's documentation is updated.
What's the risk of proceeding with installing these redistributable packages on an apparently unsupported OS? Should this be avoided completely? Or would it be reasonable to test and risk accept if successful?