Windows Server End of Life Dates: Every Version Compared

In short

Every supported Windows Server version has a fixed expiry date. The nearest deadlines: Server 2012/R2's paid ESU program ends October 13, 2026, Server 2022 leaves mainstream support on October 13, 2026, and Server 2016 hits full end of life on January 12, 2027. Server 2019 follows in January 2029. Windows Server 2025 is the current release, supported until November 2034, which is why Raff deploys it as the default for new Windows VMs. The full table, and what each date actually changes for you, is below.

The complete end-of-life table

All dates are from Microsoft's official Lifecycle pages (linked in Sources). Every version here follows the Fixed Lifecycle Policy: roughly five years of mainstream support, five more of extended support, and for some versions a paid Extended Security Updates (ESU) window after that.

Two of these dates land within months of each other: October 13, 2026 is both the final ESU cutoff for Server 2012/R2 and the end of mainstream support for Server 2022. If you only remember three dates from this table, make them October 13, 2026 (2012/R2 truly over), January 12, 2027 (2016 end of life), and January 9, 2029 (2019 end of life).

Mainstream vs extended support: What each date changes

The two support phases are frequently confused, and the difference decides how urgent your date is:

• Mainstream support covers everything: security updates, bug fixes, new features, and design changes. When it ends, the version stops improving but stays safe.
• Extended support covers security updates only. This is the phase most production servers quietly live in. When it ends, the version is end of life: no more free patches of any kind.
• Extended Security Updates (ESU) are a paid, security-only bridge Microsoft offers for some versions after EOL, priced per server and rising each year. ESU is not automatic: it is purchased through volume licensing or a Cloud Solution Provider, and in past programs the years were cumulative, so joining late meant paying for the years you skipped. ESU is a runway for a migration, not a place to live.

So "Server 2022 end of life" queries deserve a precise answer: Server 2022 is not near end of life. It leaves mainstream support in October 2026 but keeps receiving security updates until October 14, 2031.

Check which version and phase you are on

Run this in PowerShell on each server:

Get-ComputerInfo | Select-Object OsName, OsVersion, OsBuildNumber

Then map the build number to the version and its deadline:

For a fleet, run the same check remotely with Invoke-Command -ComputerName SRV01,SRV02 { Get-ComputerInfo | Select-Object CsName, OsName, OsBuildNumber } and you have your inventory in one pass. More fleet-audit commands are in our PowerShell reference for Windows VPS admins.

Windows Server 2012 and 2012 R2: The door closes in October 2026

Server 2012 and 2012 R2 went end of life in October 2023, and the third and final ESU year ends on October 13, 2026. After that there is no paid option left: every new vulnerability stays open permanently. If you still run 2012-era servers, the migration is no longer a planning item, it is overdue. Our local server to cloud migration guide covers the lift for file, app, and directory workloads.

Windows Server 2016: Full end of life on January 12, 2027

This is the big one for small businesses: a huge population of file servers, domain controllers, and SQL Server boxes still runs 2016. Free security updates stop on January 12, 2027; the paid ESU program (announced by Microsoft in February 2026) runs to January 2030 at a per-server cost that roughly doubles each year, about $5,614 per Standard server across the three years.

A related deadline hides on the same machines: SQL Server 2016 already left extended support on July 14, 2026, so the database layer on a typical 2016 box is unsupported before the OS is.

We break down the exact dates, the ESU cost math, and the three exit paths in the dedicated Windows Server 2016 end of life guide, and the tested step-by-step move is in the 2016 to 2025 migration guide.

Windows Server 2019: Plan for January 2029

Server 2019 left mainstream support in January 2024 and reaches end of life on January 9, 2029. That is far enough away that nothing is on fire, and close enough that new deployments on 2019 no longer make sense: a server built on 2019 today gets under three years of patches. Treat 2029 the way 2016 shops should have treated 2027: inventory in 2027, migrate through 2028, keep a buffer. No ESU program for 2019 has been announced yet; if Microsoft follows the 2012 and 2016 pattern, expect one, priced to make migration the cheaper path.

Windows Server 2022: Mainstream ends October 2026, patches until 2031

Server 2022 leaves mainstream support on October 13, 2026, then runs on security-updates-only extended support until October 14, 2031. Existing 2022 workloads are fine where they are. What changes after October is subtler: no new features, no non-security hotfixes, and vendor attention drifting to newer versions. For new deployments the calculus favors 2025: same licence cost on Raff, three extra years of runway, and the current feature set. The trade-offs are covered in our Windows Server version comparison.

Windows Server 2025: Supported until November 2034

Windows Server 2025 is the current Long-Term Servicing Channel release: mainstream support to November 13, 2029, extended support to November 14, 2034. It is the default OS we recommend for new Windows VMs at Raff, and the destination we test migrations against. Every Raff Windows VM ships with a 6-month Windows Server evaluation licence at no extra cost, then $15.00/month for a Standard licence through SPLA, or bring your own; current plans are on the Windows VM page.

One naming footnote: Microsoft also ships Annual Channel releases of Windows Server (such as version 23H2) aimed at container hosts. Those follow a much shorter support cycle of roughly 18 months and are not what this table covers. The dated LTSC releases above are what runs file servers, domain controllers, and business applications.

Database and mail server dates to track alongside

The OS is only one layer. The Microsoft server products that usually live on these machines expire on their own schedules (Microsoft Lifecycle):

The practical consequence: a fully patched Windows Server 2019 running SQL Server 2016 is still carrying an unsupported database today. Audit both layers, the OS with the PowerShell check above and each SQL instance with SELECT @@VERSION, before deciding what migrates when.

Which version should you deploy today

Common mistakes reading lifecycle dates

• Treating end of mainstream support as end of life. They are five years apart. Server 2022 losing mainstream support in October 2026 does not make it unsafe; it keeps security updates until 2031.
• Assuming ESU arrives automatically. ESU is a purchased subscription with a rising per-server price, not a grace period. A server without an ESU licence gets nothing after EOL day.
• Tracking only the OS date. SQL Server, Exchange, and line-of-business software carry their own lifecycles. SQL Server 2016 expired in July 2026, six months before its usual host OS.
• Deploying new servers on old versions. A fresh 2019 build today buys less than three years of patches for the same effort as a 2025 build that buys eight.
• Planning to the exact deadline. Migrations queue up in the final quarter before every EOL date. Teams that plan to finish one month early actually finish on time.

What's next

• Windows Server 2016 end of life: dates, costs, and options: the deadline that affects the most servers
• How to migrate Windows Server 2016 to 2025: the tested migration path
• Windows Server version comparison: 2019 vs 2022 vs 2025 for new deployments

Sources

• Microsoft Lifecycle: Windows Server 2016, Windows Server 2019, Windows Server 2022, Windows Server 2025, Windows Server 2012 R2
• Microsoft: Planning ahead for Windows Server 2016 end of support (February 25, 2026)
• Date last verified: 2026-08-05