Windows Server is a server operating system created by Microsoft. Currently available in eight versions, Windows Server OS consists of approximately 33.5% of the global server OS market. Our article is focused on Windows Server 2016, the second most recent release which has been generally available since October 12, 2016. The operating system comes in two editions, Standard and Datacenter. The purpose of our article is to reveal the differences and similarities between the two Windows Server 2016 versions. The key difference is in the type of workloads they can handle. Specifically, the Standard Edition does not provide some of the features available in Datacenter Edition.