12Jan 2027
The date is fixed
Windows Server 2016 extended support ends on 12 January 2027. After that date there are no security updates without a paid extended security update arrangement.
Source: Microsoft Lifecycle Policy
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- Windows Server 2016 end of support
Windows Server 2016 ends 12 January 2027.
After 12 January 2027 Microsoft stops releasing security fixes for Windows Server 2016. Every server still on it becomes a growing risk, and a finding in any audit or inspection. The options are clear; the time to choose is now.
What it covers
Windows Server 2016 end of support
Server inventory
Every server and the applications on it listed, with versions and owners.
Application compatibility
Each application checked with its vendor for support on newer Windows Server or in the cloud.
Option appraisal
Upgrade in place, rebuild on new hardware, move to Azure, replace with SaaS or buy extended security updates for a short bridge.
Migration plan
A phased plan with test, cutover and rollback steps for each server.
Budget
Costs for hardware, licences and project work, timed into the IT budget.
- Windows Server 2025
- Microsoft Azure
- Extended Security Updates
- Hyper-V
How we do it
Inventory
Servers and applications listed.
Decide
An option chosen for each server.
Migrate
Servers moved in planned waves.
Retire
Old servers decommissioned and data disposed of securely.
Field notes
Worth knowing
14Oct 2025
Windows 10 has already gone
Windows 10, Exchange Server 2016 and Exchange Server 2019 left support on 14 October 2025.
Source: Microsoft Lifecycle Policy
What you receive
- Server and application inventory
- Compatibility findings
- Option appraisal and recommendation
- Migration plan and budget
- Decommissioning records
Questions
What happens if we keep running Windows Server 2016?
It will keep working, but without security fixes. Each new vulnerability stays open, and auditors, regulators and insurers will treat it as a risk.
Can we upgrade straight to Windows Server 2025?
Often, yes, either in place or by building a new server and migrating. Application support decides which is safer.
Should we move these servers to the cloud instead?
Sometimes. End of support is a good moment to compare a cloud or SaaS option against new hardware.
More on On Premises Infrastructure
Talk to us about Windows Server 2016 end of support
Tell us what you're working on. We'll listen, ask the right questions and recommend a practical next step. No obligation.
info@gabcoenterprises.com+1 345 769 4222