Windows Server 2022 and 2016:
dates and what to do

What actually changes on 13 October 2026?

Windows Server follows Microsoft’s Fixed Lifecycle Policy: five years of mainstream support and five of extended support. Moving from one phase to the next switches nothing off; it changes what Microsoft keeps releasing.

For Windows Server 2022 the last update of the mainstream phase is the one from the Patch Tuesday of 13 October 2026. Two exceptions have practical effects: hotpatch on Datacenter: Azure Edition is supported only until the end of mainstream support, and Microsoft 365 Apps follows its own rule, covered further down.

When does each version of Windows Server expire?

The official Microsoft lifecycle dates, with the column that matters to anyone using servers as terminal servers with Office.

How do I check which versions I have?

The first step is an inventory, even a minimal one. On a single server one line of PowerShell is enough; it returns the system name, version and build number:

Get-CimInstance Win32_OperatingSystem | Select-Object Caption, Version, BuildNumber

In an Active Directory domain you can list all registered servers, from a machine with the PowerShell ActiveDirectory module (included in the RSAT tools):

Get-ADComputer -Filter 'OperatingSystem -like "*Windows Server*"' -Properties OperatingSystem, OperatingSystemVersion |
  Sort-Object OperatingSystem |
  Format-Table Name, OperatingSystem, OperatingSystemVersion -AutoSize

The Active Directory list reflects what computers have registered in the domain: accounts of decommissioned servers may still be there, and servers outside the domain do not appear. Next to each name, note the role (domain controller, file server, line-of-business application, terminal server, virtualisation host), because it is the role, not the version, that decides what to do.

What should I do, server by server?

Windows Server 2016: what happens after 12 January 2027?

After that date Microsoft no longer releases security patches for Windows Server 2016. The only exception is Extended Security Updates (ESU) delivered through Azure Arc: critical and important updates for up to three years, until 2030, with no new features or non-security fixes. The conditions published by Microsoft:

• The server must be connected to Azure Arc with the Connected Machine agent; activation has been configured from the Azure portal since 3 August 2026, with no keys to install.
• On-premises servers need Software Assurance (or an equivalent server subscription); Standard and Datacenter editions.
• Billing is monthly and starts on 13 January 2027; late enrolment means paying for the back months too, from the deadline.

ESU is a bridge for those who cannot migrate in time, not a solution: it postpones the problem and has a recurring cost. The same reasoning applies as for SQL Server 2016, often installed on these very servers.

Office on terminal servers: what changes for Microsoft 365 Apps?

If you use a Remote Desktop server so that users can work with Word, Excel and Outlook, you need to look at a different date. Microsoft supports Microsoft 365 Apps on a Windows Server only while that system is in mainstream support. For Windows Server 2022 this means: new features up to version 2608, then the apps stay on that version with security updates only, until 10 October 2028. On Windows Server 2016 and 2019 support already ended in October 2025, with the same security deadline.

The apps do not stop, but over time new Microsoft 365 features may not work as expected. Microsoft points to three destinations: Windows Server 2025, Windows 365 or Azure Virtual Desktop. If the terminal server is mainly there so users can work remotely, a cloud desktop is worth considering: we covered it in Azure Virtual Desktop without Active Directory.

How do you move to Windows Server 2025?

Microsoft’s documentation provides several routes; the choice depends on the server’s role more than on the starting version.

• 1In-place upgrade — keeps settings, roles and data. Windows Server 2025 accepts a direct jump from Windows Server 2012 R2 onwards for non-clustered servers; clusters using a rolling upgrade move up one version at a time. From Windows Server 2019 and 2022 you can also upgrade via Windows Update, with at least the March 2026 cumulative update installed. Not all roles support an in-place upgrade: check beforehand.
• 2Domain controllers: never in-place — Microsoft explicitly advises against it because the upgrade does not bring the Active Directory improvements of Windows Server 2025. You install a new server, promote it to domain controller and decommission the old one.
• 3Clean installation or migration — when you change hardware or want to start from a clean environment, roles and data move to a new server, physical or virtual.
• 4Moving the workload to the cloud — for terminal servers, Azure Virtual Desktop or Windows 365; for applications, a virtual machine in Azure with our cloud IT services.

What to do this month

• Take an inventory of your servers with version, build and role, using the commands above.
• Flag every Windows Server 2016 and decide for each one: upgrade, migration, decommissioning or ESU as a bridge.
• Check that your Windows Server 2022 machines have installed the 13 October update and keep receiving the monthly patches.
• Check the Microsoft 365 Apps version on your terminal servers (in Word: File, Account, About Word) and set a date for the move before 10 October 2028.
• Put the deadlines and the decisions taken in writing: for organisations within the scope of NIS2 system lifecycle management is part of the security measures to be documented.