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Windows Server 2016 End of Life: January 12, 2027, ESU and Upgrades

By Scott Bissett  ·  Published: September 18, 2026  ·  Reference guide  ·  Dates read at Microsoft's product lifecycle page and Microsoft Learn on the day of publication.

Windows Server 2016 reaches end of life on January 12, 2027. That is the end of extended support on Microsoft's product lifecycle page, and it is the last day Microsoft ships a security update for it without a paid add-on. Mainstream support, the phase with new features and non-security fixes, already ended on January 11, 2022. The release shipped on October 15, 2016, so it will have had a little over ten years. Microsoft's page notes that containers released with Windows Server 2016 follow the same dates.

Microsoft has announced Extended Security Updates for it, and you do not have to buy them if you move in time. The rest of this page is the detail: what stops, what ESU does and does not cover, what Microsoft has published about buying it, and which upgrade target gives you the most runway.

What ends on that date. Security updates, non-security fixes, and assisted support under a standard agreement. The server keeps running. Every vulnerability found in it afterwards stays open unless the machine is enrolled in Extended Security Updates, and Windows Server flaws are a regular feature of CISA's Known Exploited Vulnerabilities catalog. Our live risk read for the release is on the Windows Server 2016 page.
Quick answer: Windows Server 2025 is supported until November 14, 2034, its end-of-support date. Active support for Windows Server 2025 ends on November 13, 2029; security fixes continue until that end-of-life date. The next Windows Server version to reach end of life is 2016, on January 12, 2027. 16 of 20 tracked Windows Server versions are past end of life; the most recent to reach it, 23H2 AC, did so on May 12, 2026. Every Windows Server version's release and end-of-support date is on the Windows Server lifecycle page.

The dates, in one table

MilestoneDateSource
ReleaseOctober 15, 2016Microsoft product lifecycle page
End of mainstream supportJanuary 11, 2022Microsoft product lifecycle page
End of extended support (end of life)January 12, 2027Microsoft product lifecycle page
ESU can be configured in the Azure portalAugust 3, 2026Microsoft Learn, Azure Arc ESU page
Billing begins for ESUs enabled by Azure ArcJanuary 13, 2027Microsoft Learn, Azure Arc ESU page
ESU coverageUp to three years, through 2030Microsoft Learn, Azure Arc ESU page

Microsoft's pages give the ESU period as "up to three years, through 2030" and do not state the final day. We print what Microsoft prints. Where a calendar day for the end of ESU appears elsewhere, including the day our own product page inherits from the community dataset, treat it as an estimate until Microsoft publishes one.

Running Windows Server past end of life?
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Extended Security Updates: what Microsoft has published

Microsoft announced ESU for this release on its Windows Server blog with the sentence "Today, we are announcing Extended Security Updates for Windows Server 2016." The operational detail is on Microsoft Learn:

What we could not verify. The Microsoft pages we read do not state a price for Windows Server 2016 ESU. Earlier ESU programs have priced each year higher than the last, and that is a pattern, not a published number for this one. Budget on a quote from your licensing partner, not on a blog.

Where to move: three targets, three very different runways

Windows Server 2016 can upgrade in place to 2019, 2022 or directly to 2025. The supported paths and their conditions are in our guide to every Windows Server version. What differs is how long each target lasts:

TargetMainstream support endsExtended support endsRead
Windows Server 2025November 13, 2029November 14, 2034The longest runway, and the only target still early in mainstream support.
Windows Server 2022October 13, 2026October 14, 2031Mainstream support ends before 2016 itself expires. Security updates continue to the extended date.
Windows Server 2019January 9, 2024January 9, 2029Already out of mainstream support. Buys two years and another migration.

Moving a 2016 server to 2019 to "get supported" trades one deadline for another that arrives two years later, on January 9, 2029. If the application stack allows it, the 2025 target spends the migration effort once.

What else is on the same server

A Windows Server 2016 host rarely ages alone. SQL Server 2016 reached the end of extended support on July 14, 2026, and its own Extended Security Updates story is separate from the operating system's: different product, different enrollment, different bill. Windows Server 2012 and 2012 R2 reach the end of their third and final ESU year on October 13, 2026, so an estate that parked those servers on ESU has a harder deadline than this one, and sooner. The .NET Framework versions on the box follow the operating system's lifecycle; modern .NET does not, and .NET 8 and 9 both end before this server does.

What to do, in order

  1. Count them. Inventory every Windows Server 2016 instance, including containers built on its base images and the ones nobody admits to owning. Our EOL Checker and API answer the date question for the rest of the stack in the same pass.
  2. Split the list. Servers that can move before the date, and servers that cannot because an application, a vendor certification or a change freeze says so.
  3. Move the first group to 2025 where the application supports it, 2022 where it does not.
  4. Enroll the second group in ESU early. The Azure portal has accepted configuration since August 3, 2026 and nothing is billed before January 13, 2027. Finishing the Azure Arc onboarding in the autumn costs nothing and removes the risk of a January scramble.
  5. Treat ESU as a bridge with an end. It runs for up to three years and delivers security updates only. Put the retirement date of each ESU server in the plan on the day you enroll it.

Frequently Asked Questions

When is Windows Server 2016 end of life?

Windows Server 2016 reaches the end of extended support on January 12, 2027, per Microsoft's product lifecycle page. Mainstream support ended on January 11, 2022. After the end date Microsoft ships no further security updates unless the server is covered by Extended Security Updates.

Is there an ESU for Windows Server 2016?

Yes. Microsoft announced Extended Security Updates for Windows Server 2016 on its Windows Server blog in February 2026. Microsoft Learn describes them as Critical and Important security updates for up to three years, through 2030. They can be configured in the Azure portal from August 3, 2026, billing for ESUs enabled by Azure Arc begins January 13, 2027, and Software Assurance through a Volume Licensing program is required to purchase them.

Is Windows Server 2016 ESU free on Azure?

Microsoft Learn states that Azure VMware Solution machines and virtual machines on Azure Local are eligible for free ESUs and should not enroll in ESUs enabled through Azure Arc. For servers elsewhere, ESUs enabled by Azure Arc are a paid, pay-as-you-go monthly subscription.

What should I upgrade Windows Server 2016 to?

Windows Server 2016 can upgrade in place to Windows Server 2019, 2022 or directly to 2025. Windows Server 2025 has the longest runway: mainstream support to November 13, 2029 and extended support to November 14, 2034. Windows Server 2019 is already out of mainstream support and ends on January 9, 2029.

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