Can someone explain Windows Server upgrade licensing?

I have a student license for Windows Server I got from a course I took some time ago. I believe is is Windows Server 2016? (Sorry for not being sure, it’s not installed and I don’t have the info handy.) My question is basically this: With the desktop client, Windows 10 is the “last” version, forever being updated. Is it the same case for Windows Server? Does that 2016 version get updated automatically to something from 2019, or is each version update required to be purchased?

No. No one can explain windows licensing. It is literally incomprehensible.

Ok now that I’ve gotten the snark out of my system. No you don’t get the same “upgrade rights” with Windows server. If you have a 2016 Licence, then that what your have. You will need to buy a 2019 licence if you want to use server 2019.


I suspect that Windows server will probably keep getting new iterations as time goes on but that is because Windows server is a completely different type of OS and more commercial that other OS’s.

I could be wrong but I have not really heard anything that has said that Windows server was going to be treated like Windows 10.

Exactly, Windows Server 2016 received feature updates for a while, then Server 2019 came out and it gets the feature updates. You don’t get automatic update to the next version, unless you also have SA (Software Assurance) tied to your corporate server licensing.

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I can quickly clear up a few items here.

  • A student license would be MDSNAA, Spark, Education store, Download Subscription.
  • Windows 10 is still released as an edition. This may include build updates or upgrades. Future versions such as Windows 10X are not inclusive of this subset.

As per the above, with the exception of download subscriptions acquired by your educational institution or through retail, these licenses assigned to you are version specific with no downgrade or upgrade rights.

Windows 10 or desktop versions may be acquired through the same channels or separately. Your educational institution may also acquire a license through SA/VL for your use of their facilities which would entitle you to upgrade and/or downgrade rights for the product on their own terms.

In any case, simply having a license for Windows Server does not entitle you to upgrade to newer editions. Otherwise you would need Software Assurance or a Volume License agreement.

By the terms of the agreement you signed, you may or may not be allowed to keep a copy of Windows Server 2016. If the terms of the subscription or benefits have allowed it, you are allowed to order and install a copy of a Windows Server upgrade package with any CALs you may have received according to their licensing terms.