Windows Server 2016 End of Life: Your Options Before 12 January 2027

The Windows Server 2016 end of life is fixed: extended support ends on 12 January 2027, less than three months from now. After that date Microsoft provides no regular security updates for this version. The server keeps running, but newly discovered vulnerabilities are no longer fixed. This article explains what the date means and which routes are open to you. For general planning of support dates, see Planning for end of support in Microsoft products.

What the date means

Windows Server 2016 was released on 15 October 2016. Mainstream support ended on 11 January 2022, and since then the version has been in extended support. That phase ends on 12 January 2027. The difference between the two phases is explained in Windows Server 2022 end of life.

What happens after the end

The software starts and works as before. Newly found vulnerabilities, however, stay open. For a file server on a separate network this may be acceptable. For a server with a connection to the outside it is a real risk.

Option 1: keep running it in an isolated environment

If you do not have to replace the server, you can keep operating it. That is only defensible if it has no internet connection and is reached by a few known systems, for example a machine controller. The risk remains and sits with you. Plan to document this decision.

Option 2: Extended Security Updates

Microsoft offers Extended Security Updates (ESU) for Windows Server 2016. According to Microsoft they deliver critical and important security updates for up to three years after end of support, that is from January 2027 to January 2030. The conditions:

• They apply to the Standard and Datacenter editions.
• As a rule they require Software Assurance through a volume licensing program.
• They are obtained through the Azure portal, billed monthly by usage.
• They do not extend technical support.

The Microsoft sources we read give no price. They also do not say whether a license acquired second-hand meets the Software Assurance condition. Clarify this with Microsoft before you book.

Option 3: move to a newer version

Microsoft recommends moving to Windows Server 2025. According to Microsoft's upgrade table, a direct upgrade from Windows Server 2016 to 2019, 2022 and 2025 is possible. Every Windows Server version, however, needs its own license. A perpetual license of the successor version can be bought used. The terms of the successors:

• Windows Server 2019: extended support until 09 January 2029.
• Windows Server 2022: extended support until 14 October 2031.
• Windows Server 2025: extended support until 14 November 2034.

More on choosing between the versions in Windows Server 2019 end of life.

Access licenses when you move

CALs are often forgotten in a version change. The CAL must be at least as current as the server being accessed. A Windows Server 2016 CAL does not cover a Server 2022. The reverse works: a newer CAL also covers older servers. Anyone migrating should therefore buy the CALs in the target version right away. How to work out the number is described in How many Windows Server CALs do I need?

Four questions before you decide

• Can the server be reached from the internet, or only from a separate network?
• Which edition and how many cores are licensed?
• Which CAL version do you hold, and how many people and devices access the server?
• Should the system run until a planned replacement, or permanently?

The answers show whether continued operation, ESU or a move is the right route. If you move, it pays to obtain the licenses before the migration starts, so that the new installation is licensed from day one.

Buying used: the legal framework

In its judgment C-128/11 of 03 July 2012 the Court of Justice of the European Union held that the distribution right in a computer program is exhausted once it has been sold with the right holder's consent. This also applies where the software was delivered by download. Whoever resells must make their own copy unusable. The first acquirer may not split up a client-server license that covers more users. How this can be evidenced in practice is described under Is used software legal?

What Lizenzus does for you

We supply used, perpetual licenses for Windows Server, with a documented chain of title. Describe your environment to us: server version, edition, core count and the number of people and devices accessing it. We tell you which licenses your target version requires and give you the pricing. A request is non-binding.

Read more: Buy a Windows Server license and Windows Server 2025 Standard.