Published October 19, 2026
What ends on January 12, 2027
Extended Support for Windows Server 2016 ends on January 12, 2027. Mainstream Support ended in January 2022. The dates cover the Datacenter, Standard, Essentials and MultiPoint Premium editions, and containers released with Windows Server 2016.
After that date Microsoft stops security updates and technical assistance. Non-security updates already ended with Mainstream Support. The server keeps running. Under Microsoft's Fixed Lifecycle Policy, security updates after end of support come only through the paid Extended Security Update program.
Support for Microsoft 365 Apps on Windows Server 2016 ended on October 14, 2025. Microsoft continues security updates for those apps on Windows Server 2016 until October 10, 2028, on Version 2602. Extended Support for SQL Server 2016 ended in July 2026. A Windows Server 2016 machine that runs SQL Server 2016 now has two products past end of support.
The decision for each server
Make the decision per server, not per estate. Give each Windows Server 2016 machine one of five labels: upgrade in place, rebuild on a newer version, move to Azure, cover with Extended Security Updates for a fixed time, or retire.
Let the application on the server set the label. A server whose application vendor supports a newer Windows Server can be upgraded. A server whose application has no supported path needs a bridge, and the bridge needs an end date.
The options
| Option | What it involves | What to check |
|---|---|---|
| Upgrade in place | Install a newer version over Windows Server 2016, keeping roles, settings and data. Supported directly from 2016 to 2019, 2022 or 2025 with installation media. | Whether each role supports in-place upgrade, and a full backup first. |
| Rebuild and migrate | Build a new server on a supported version and move the application and data to it. | Application vendor support for the target version, and a cutover window. |
| Cluster OS rolling upgrade | Upgrade failover cluster nodes one at a time while Hyper-V or Scale-Out File Server workloads keep running. | Clusters move one version at a time: 2016 to 2019, then 2022, then 2025. |
| Move to Azure | Move the virtual machine to Azure as it is, or rebuild it there. | Whether Windows Server 2016 Extended Security Updates in Azure carry a charge for your agreement, in writing. |
| Extended Security Updates | Pay monthly for security updates through Azure Arc while the application is replaced or recertified. | Eligibility, price and core count for each server. |
| Retire | Switch off servers with no owner or no remaining use. | Data retention needs before the disks are wiped. |
The target version sets the next deadline. Extended Support ends in January 2029 for Windows Server 2019, October 2031 for Windows Server 2022 and November 2034 for Windows Server 2025. Windows Server 2022 left Mainstream Support in October 2026. Choosing 2019 starts the same program again in about two years.
The order of the work
- Inventory every Windows Server 2016 instance. Include physical hosts, virtual machines, cluster nodes, domain controllers and container hosts. Record edition, installation type (Server Core or Desktop Experience), roles, and what else is installed, such as SQL Server or Microsoft 365 Apps.
- Name an owner for each server. Servers without an owner are candidates to retire. Give the owner a date to object.
- Get the application vendor's position in writing. For each application, record which Windows Server versions the vendor supports and at which application version.
- Label every server. Upgrade, rebuild, move, cover or retire, with a target date for each.
- Settle the bridge early. Windows Server 2016 Extended Security Updates could be configured in the Azure portal from August 3, 2026. Connect the servers that need them to Azure Arc and confirm eligibility and price before January 12, 2027.
- Pilot each server type. Upgrade or rebuild a few non-critical servers of each role. Measure the hours and downtime each takes. Those figures turn the plan into a schedule.
- Run the waves, then the stragglers. Group servers by application so an application moves together. Track the stragglers by name, with an owner and a date.
- Decommission. Remove upgraded and retired servers from patching, monitoring, backup and license counts.
What to plan extra time for
- Application vendor answers. A vendor may support only its latest application version on a newer Windows Server, which turns an operating system upgrade into an application upgrade.
- Clusters. A rolling upgrade from 2016 to 2025 is three upgrades, each with its own testing and change window.
- Domain controllers. Microsoft publishes separate upgrade guidance for them and recommends promoting new domain controllers on a clean install over upgrading existing ones in place. Plan them as their own workstream.
- Paired products. A server running SQL Server 2016 needs a database decision as well as an operating system decision, and the two support matrices have to agree.
- Servers with no owner, no vendor or no test environment. Name them early and give each one a decision date.
The restrictions plans leave out
Microsoft's restrictions for in-place upgrades of licensed Windows Server include these:
- An upgrade keeps the edition. Standard can move to Datacenter or Datacenter: Azure Edition during the upgrade. Datacenter cannot move to Standard.
- An upgrade cannot switch between Server Core and Desktop Experience.
- An upgrade cannot change the language.
- NIC Teaming must be disabled before the upgrade and can be re-enabled after.
- Servers that boot from VHD, and Windows Storage Server editions, cannot be upgraded in place.
- Support for in-place upgrades varies by cloud provider. Check with yours.
Not every role supports in-place upgrade. Check each role against Microsoft's role and feature migration matrix before choosing the method.
Licenses and Extended Security Updates
Each Windows Server upgrade needs a license for the target version. Count the cores for every upgraded or rebuilt server before the budget is set.
Extended Security Updates for Windows Server 2016 are available through Azure Arc. They cover Critical and Important security updates for up to three years, through 2030. They include no new features, no customer-requested non-security fixes and no general technical support. Microsoft calls the program a last resort and a temporary bridge.
Under Azure Arc, Standard and Datacenter editions are covered. The servers need Software Assurance through a Volume Licensing program, a Server Subscription, or SPLA licensing. Billing is monthly and starts on January 13, 2027. Licenses provisioned later are back-billed to January 12, 2027. Each license has a minimum of 16 physical cores per machine or 8 virtual cores per virtual machine. The free disaster recovery and Visual Studio dev/test benefits offered for Windows Server 2012 do not apply to Windows Server 2016.
Since April 1, 2026, Microsoft charges the same list price for new Extended Security Updates in Azure, on-premises and other clouds. Its Azure Local documentation names Windows Server 2016 as subject to that pricing. Get the price per core in writing from your Microsoft account team or partner.
Skills and operations
Expect the effort to sit in application testing, change windows and chasing owners. Give one person the job of tracking every server by name, with its label, owner and date.
Track servers covered by Extended Security Updates separately. Patching tools should show which servers are covered, and each covered server needs a recorded exit date. Reduce the cores on the Azure Arc license as servers leave, since billing follows the provisioned cores.
Settle these first
- How many Windows Server 2016 instances do you run, and how many have a named owner?
- Which applications have a vendor-supported path to Windows Server 2022 or 2025, in writing?
- Which servers also run SQL Server 2016 or Microsoft 365 Apps?
- Which servers will not be finished by January 12, 2027, and what will covering them cost?
- Do those servers have active Software Assurance, a Server Subscription or SPLA licensing?
- Which target version, and does it give you enough years before the next deadline?
Questions
- When does Windows Server 2016 support end?
- Extended Support ends on January 12, 2027. Mainstream Support ended in January 2022. After January 12, 2027, Microsoft provides security updates only through the paid Extended Security Update program.
- Will Windows Server 2016 stop working after end of support?
- No. The server keeps running. It receives no security updates or technical assistance unless it is covered by Extended Security Updates.
- Can we upgrade Windows Server 2016 straight to Windows Server 2025?
- Yes, for servers that are not clustered. Microsoft supports an in-place upgrade from Windows Server 2016 to 2019, 2022 or 2025 with installation media. Failover clusters using a rolling upgrade move one version at a time.
- Are Extended Security Updates available for Windows Server 2016?
- Yes, through Azure Arc. They cover Critical and Important security updates for up to three years, through 2030. Billing is monthly from January 13, 2027, and the servers need Software Assurance, a Server Subscription or SPLA licensing. Confirm the price with your account team.
- Does an upgrade need a new license?
- Yes. Each Windows Server upgrade requires a license for the target version. The upgrade keeps the edition unless you move from Standard to Datacenter during it.