Windows Server 2016 End of Support Is January 12, 2027: Upgrade, Move, Pay or Retire

Windows Server 2016 reaches end of support on January 12, 2027. After that date, Microsoft stops shipping security updates for it, unless you enroll the server in paid Extended Security Updates. That is about nine weeks from today.

This piece is for small organizations and the agencies that support them: the nonprofit with one file server in a closet, the association with an aging domain controller, the office with an IIS site or an old line-of-business app. It covers what else ends that week, how to find the affected boxes, and the four ways out.

The short version: list every server running Windows Server 2016 this month. For each one, pick one of four paths: upgrade or migrate to Windows Server 2025, move the workload to Azure, buy Extended Security Updates, or retire it. Domain controllers and file servers are the easiest to move. Old apps on .NET Framework 4.6.2 take the most testing, so start with them.

What ends on January 11 and 12, 2027

Microsoft’s 2027 end of support list groups a lot of products onto two days. The Windows Server 2016 family ends on January 12. Several server products that often run on it end one day earlier.

The Windows Server 2016 lifecycle page shows the extended end date as January 13, 2027 at 6:59:59 AM Pacific. That is Microsoft’s way of marking the end of January 12. The page covers the Datacenter, Essentials, MultiPoint Premium and Standard editions, and says containers released with Windows Server 2016 follow the same dates.

Visual Studio 2022 is the odd one out. Under Microsoft’s Fixed Lifecycle Policy, extended support still includes security updates. Non-security fixes and feature requests stop.

What Windows Server 2016 end of support actually stops

The server keeps running on January 13. Nothing shuts off. What stops is the monthly flow of security fixes, plus Microsoft technical support for the product.

That matters most for anything facing the internet or holding member data. An IIS site or a file server full of finance records becomes an easy target once new flaws go unpatched. Our ransomware primer explains why unpatched servers are a common way in.

Two related dates are easy to miss:

• SQL Server 2016 is already out. Its extended support ended in July 2026, according to its lifecycle page. Many Windows Server 2016 boxes run it. It has its own paid security update years.
• Microsoft 365 Apps on Windows Server 2016 lost support on October 14, 2025. Microsoft says it will keep sending security updates for those apps until October 10, 2028, per its Microsoft 365 Apps guidance. That does not cover the server underneath.

Find every Windows Server 2016 box first

Small organizations rarely have one clean list. Servers hide as virtual machines, or as a "temporary" box a past vendor set up.

Check the computer list in Active Directory, your hypervisor console and your backup tool. Each shows servers the others miss. If you keep an asset register, compare all three against it. Our IT asset management basics post covers how to keep one going after this.

For each server, write down four things:

1. What it does: file shares, domain controller, IIS site, app server, Hyper-V host, print, or something else.
2. What software runs on it, with versions, including SQL Server and .NET Framework.
3. Who owns the app, and whether a vendor supports it on newer Windows Server.
4. Whether it is physical or virtual, and how old the hardware is.

That list decides the path for each box. A Hyper-V Server 2016 host needs extra care, because every guest on it depends on the host getting patched too.

Option 1: Upgrade or migrate to Windows Server 2025

Microsoft’s upgrade planning page lists a direct in-place upgrade from Windows Server 2016 to Windows Server 2025. It says nonclustered systems "can upgrade up to four versions at a time." Clusters still move one version at a time.

An in-place upgrade keeps settings, roles, features and data. It also has limits. You cannot switch between Server Core and Desktop Experience during it. NIC Teaming must be turned off first. Not every role supports it, so check Microsoft’s role migration matrix.

For most small shops, a clean build is the safer path for two common roles:

• Domain controllers. Microsoft’s domain controller guidance calls promoting new servers and demoting the old ones “the recommended way to upgrade a domain.” Promoting a new server runs the adprep steps for you. Then you move the FSMO roles and demote the old DC.
• File servers. Storage Migration Service, run from Windows Admin Center, inventories the old server, copies shares and security settings, and can hand the old server’s identity to the new one so users keep their paths.

Pick the target with its own dates in mind. Windows Server 2025 has extended support until November 2034. Windows Server 2022 moved to extended support in October 2026 and ends in October 2031. Server licensing and hardware costs apply either way. Our post on server memory prices covers why refresh quotes have gone up this year.

Option 2: Move the workload to Azure

Moving a Windows Server 2016 virtual machine to Azure is the path Microsoft has long tied to free Extended Security Updates. Its ESU FAQ, updated in August 2026, still says ESUs "are free for VMs in Azure." It lists Azure Virtual Machines, Dedicated Host, Azure VMware Solution, Nutanix Cloud Clusters on Azure and the Azure Stack portfolio.

There is a catch. On March 27, 2026, Microsoft’s licensing team announced a standardized ESU pricing model. It says new ESU offerings for Windows and SQL Server released from April 1, 2026 carry the same list price wherever you deploy, Azure included. Earlier offerings such as Windows Server 2012 ESUs keep their old terms. The notice does not name Windows Server 2016.

Azure can still make sense without free updates, since it removes the hardware refresh. Our explainer on SaaS, PaaS and IaaS helps sort which apps belong on a VM and which belong on a managed service.

Option 3: Buy Extended Security Updates

For servers that cannot move in time, ESUs buy up to three years. Microsoft’s Azure Arc ESU page says Windows Server 2016 ESUs provide "Critical and Important security updates for up to three years, through 2030." Microsoft announced general availability of ESUs through Azure Arc in August 2026.

What the Arc page says, as of October 2026:

• Setup in the Azure portal opened August 3, 2026. Billing starts January 13, 2027.
• Standard and Datacenter editions are covered. The Azure Connected Machine agent must be version 1.62 or later.
• You need Software Assurance through a volume licensing program, such as an Enterprise Agreement or Open Value. Servers licensed through SPLA or a Server Subscription do not need it.
• Arc billing is pay-as-you-go and monthly, so you can stop paying when a server is migrated.

Microsoft also sells yearly ESUs through volume licensing. ESUs include no new features and no technical support, according to the ESU FAQ, which calls the program "a last resort paid option."

Microsoft had not published a Windows Server 2016 ESU price as of October 2026, according to SCHNEIDER IT MANAGEMENT. Price it with your partner before you assume ESUs are cheaper than a new server.

Option 4: Retire the server

Some boxes are not worth saving: shares already copied to SharePoint, a microsite for a past event, an app the vendor now hosts.

Confirm nothing still connects to it: check event logs, open sessions, scheduled tasks and DNS records. Take a final backup and keep it where you can restore it. Our data backup strategy and disaster recovery planning posts cover what a usable final copy looks like. Then shut it down for a few weeks before you wipe it, so anything you missed surfaces while you can still restart it.

.NET Framework 4.6.2 apps: move to 4.8 or 4.8.1

.NET Framework 4.6.2 ends on the same day as Windows Server 2016. Microsoft’s .NET Framework lifecycle FAQ says 4.6.2 "follows the Lifecycle Policy of the parent OS." It recommends moving to .NET Framework 4.8.

The good news is that 4.x versions are in-place updates. The same FAQ says apps built on earlier 4.x versions should run on 4.6.2 and later without recompiling. It also notes a small number of changes that may break things, so test first.

Watch which version fits which server. Microsoft’s versions page lists 4.8 as installable on Windows Server 2016. It lists 4.8.1 only for Windows Server 2022 and 2025. And 4.8 on a 2016 box follows that box’s lifecycle, so it does not buy time past January 12. The lasting fix is a newer server running 4.8 or 4.8.1.

What our other end-of-support posts already cover

We have covered the nearby dates elsewhere:

• Modern .NET and Umbraco. .NET 8 is a different product from .NET Framework, with its own clock. The .NET 8 and Umbraco 13 post covers the November 10 and December 14 dates.
• The full quarter. The Q4 2026 platform calendar lists CMS, PHP, .NET and browser dates, plus Windows Server 2012 ESU Year 3 ending and Windows Server 2022 moving to extended support.
• Office and Windows 11. Our post on Office 2021 and Windows 11 24H2 covers the October 13 desktop dates.

A nine-week plan for Windows Server 2016

1. This week: build the server list and mark each box upgrade, Azure, ESU or retire.
2. Next two weeks: ask app vendors in writing which Windows Server and .NET Framework versions they support.
3. By early December: stand up new domain controllers and start file server copies.
4. By mid-December: get ESU and Azure pricing in writing for anything that cannot move.
5. Before January 12: enroll the leftovers in ESUs, and shut down what you are retiring.

Holidays shorten December. Plan for fewer working days than the calendar shows.

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