The different generations of Windows Server, like , , , are called 'Versions' by Microsoft. The different flavors of one version, like R2 Standard, Datacenter, Essentials, or Foundation, are called 'Editions' by Microsoft. Not necessarily related to the version or edition, there are several license types. To make matters even worse, there are two primary installation types MSI and click-to-run , and a few different key 'silos'. For instance, if you have an Office Pro Plus subscription license as part of an Office E3 subscription, you can use that either for a click-to-run installer or an MSI installer from retail media.
In my experience, Volume licenses are in their own 'silo' and OEM licenses are in their own 'silo'. That means Volume keys must be used with Volume media, and you often need to use Volume media or installers downloaded from the VLSC to upgrade an in-place Volume product.
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