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Windows Server
A family of Microsoft server operating systems that support enterprise-level management, data storage, applications, and communications.
12,535 questions
There is no direct, in-place upgrade from Windows Server 2008 R2 to Windows Server 2019 It is a multiple step process. It is highly recommended that you perform a clean installation of the newer version of the operating system. Not only is it likely to take less time to accomplish, but you are provided with a system that does not have any artifacts from earlier software installs/de-installs. When it comes to debugging, you don't have to factor in any anomalies that may be there as a result of an in-place upgrade.
Additionally, before you start your upgrade, you should ensure that your hardware supports the version of Windows Server you are going to be installing. Very little hardware that was around in 2008 R2 timeframe still supports the latest versions of the OS. See windowsservercatalog.com for hardware compatibility. This does not mean that it will definitely no run. It means that it is not supported by either the hardware vendor or Microsoft. If hardware support is not an issue for you, you may very well be able to get it to run. It just means you will be operating an environment without official support. You may have to install drivers that are not supported and have not been tested, but they still appear to work.
