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Guide · Windows Server

Windows Server 2016 end of life: 12 January 2027, dates and options

Updated · Rotomal

Windows Server 2016 end of life (end of support) is 12 January 2027 in every edition (Datacenter, Essentials, MultiPoint Premium and Standard), and the January 2027 security update is the last. Extended Security Updates are offered for Standard and Datacenter through January 2030; through Azure Arc they cost about $5.21 per core a month for Standard in Microsoft's price list, with a 16-core minimum per physical server. Your options are an in-place upgrade to Windows Server 2019, 2022 or 2025, a migration to new hardware or Azure, or ESU while you move.

Key dates

DateWhat happens
15 October 2016Windows Server 2016 lifecycle start
January 2022Mainstream support ended; extended support (security updates) continued
14 October 2025Support for Microsoft 365 Apps on Windows Server 2016 ended; security updates for those apps continue to 10 October 2028
14 October 2026Microsoft's 90-day reminder posted in the Windows message center
12 January 2027End of support for all editions; last security update; Essentials features unsupported; ESU period starts for Standard and Datacenter
13 January 2027Billing for ESU enabled by Azure Arc begins
January 2030End of ESU coverage (Microsoft: 12 January 2027 through January 2030)

Is it 12 or 13 January 2027?

12 January 2027. Microsoft's end-of-support list for 2027 and its Windows message center both give 12 January 2027. The Windows Server 2016 product lifecycle page shows the cut-off as a timestamp in Pacific Time, 1/13/2027 6:59:59 AM, which is why some sites quote 13 January.

What end of support means

  • No new security updates, non-security updates, free or paid assisted support, or online technical content updates from Microsoft.
  • The server keeps running; vulnerabilities found after 12 January 2027 stay unpatched unless you are covered by ESU.
  • For Windows Server 2016 Essentials, Microsoft says any Essentials capability that continues to function after end of support should be treated as unsupported, including Remote Web Access.

Your options

OptionGood forCost published by MicrosoftWatch out for
In-place upgrade to Windows Server 2025Same hardware, roles that support in-place upgradeStandard: $1,176 for 16 cores (US MSRP), plus CALsBack up first; restrictions; domain controllers have their own guidance
Migrate to a new serverOld hardware, domain controllers, file serversLicence as above, plus hardwareRole-by-role migration takes planning
Move the server to AzureRetiring on-premises hardwareAzure resources billed; 2016 ESU on Azure VMs billed at the same $0.007132 per vCPU-hourFree ESU in Azure was a 2012 benefit, not a 2016 one
Extended Security Updates on-premisesServers that cannot move before JanuaryAzure Arc: about $5.21 per core a month (Standard) or $29.98 (Datacenter); 16-core minimum per physical server, 8 per VMStandard and Datacenter only; Software Assurance, server subscription or SPLA; back-billed to 12 January 2027 if bought late
Retire the serverJobs that already moved to the cloudNoneCheck for hidden dependencies first

Windows Server 2022 moved to extended support on 13 October 2026, while Windows Server 2025's lifecycle runs into November 2034, which makes 2025 the usual target for an upgrade today.

Windows Server 2016 ESU cost

Microsoft's Azure Retail Prices API lists Windows Server 2016 ESU enabled by Azure Arc at $0.007132 per core per hour for Standard and $0.041067 for Datacenter, effective 1 August 2026 (checked 3 November 2026). For a physical Standard server at the 16-core minimum that is about $83 a month or $1,000 a year, close to the $1,176 list price of a new Windows Server 2025 Standard licence for 16 cores. Our Windows Server 2016 ESU cost guide has worked examples, the rules on minimums and back-billing, and why moving to Azure no longer makes ESU free.

Windows Server lifecycle: end dates for every version

VersionMainstream support ended or endsExtended support (end of life)
Windows Server 2012 and 2012 R29 October 201810 October 2023; paid ESU ended 13 October 2026
Windows Server 201611 January 202212 January 2027; ESU through January 2030
Windows Server 20199 January 20249 January 2029
Windows Server 202213 October 202614 October 2031
Windows Server 202513 November 202914 November 2034

Microsoft's lifecycle pages show each cut-off as a timestamp at 6:59:59 AM Pacific Time on the following day, so the pages read 1/13/2027 for Windows Server 2016. Essentials editions share their version's dates.

Supported upgrade paths from Windows Server 2016

  • Back up the server and important files first.
  • No language change, and no switch between Server Core and Desktop Experience, during the upgrade.
  • Standard stays Standard unless you move up to Datacenter; you cannot downgrade from Datacenter.
  • Disable NIC Teaming before the upgrade; Storage Server editions and boot-from-VHD servers cannot be upgraded in place.
  • Each Windows Server upgrade needs a separate licence for the new version.
TargetIn-place from installation mediaThrough Windows Update
Windows Server 2019YesNot listed for 2016
Windows Server 2022YesNot listed for 2016
Windows Server 2025YesNot listed for 2016 (listed from 2019 and 2022)

Remote Desktop hosts running Office

Support for Microsoft 365 Apps on Windows Server 2016 ended on 14 October 2025. Microsoft keeps providing security updates for Microsoft 365 desktop apps on Windows Server 2016 until 10 October 2028, but feature updates stopped at Version 2602. Where the server's Windows version no longer supports Microsoft 365 Apps, Microsoft recommends moving those users to Windows 365 or Azure Virtual Desktop.

Where to start

List every 2016 server and what it does, then decide per server: upgrade, migrate, move, buy time or retire. Server 2016 Exit Plan does exactly that for a fixed $199 per server: a read-only inventory, Microsoft's upgrade rules applied to your roles and applications, licence and ESU lines to budget, and a runbook your team or IT provider can follow.

Questions

Is Windows Server 2016 still supported?

Until 12 January 2027, in extended support, which means security updates only. After that date it gets no more updates unless covered by Extended Security Updates.

How much does Windows Server 2016 ESU cost?

Through Azure Arc, $0.007132 per core per hour for Standard (about $5.21 per core a month) and $0.041067 for Datacenter (about $29.98), in Microsoft's price list on 3 November 2026. A physical server has a 16-core minimum, so Standard ESU starts at about $83 a month. Billing starts on 13 January 2027.

Which Windows Server versions reach end of support in 2026 and 2027?

In 2026, paid ESU for Windows Server 2012 and 2012 R2 ended on 13 October, and Windows Server 2022 left mainstream support the same day (its extended support runs to 14 October 2031). In 2027, Windows Server 2016 reaches end of support on 12 January.

Can I upgrade Windows Server 2016 directly to 2025?

Yes. Microsoft supports an in-place upgrade from 2016 to 2025 using installation media. The Windows Update route to 2025 is listed only from 2019 and 2022.

Does ESU cover Windows Server 2016 Essentials?

No. Microsoft's end-of-support notice offers ESU for Standard and Datacenter editions, and says Essentials features become unsupported on 12 January 2027.

What happens to Remote Web Access?

Microsoft support for Windows Server 2016 Essentials features, including Remote Web Access, ends on 12 January 2027. Plan a replacement for remote access before then.

Sources

Guides and answers