Last updated: 7 November 2026
Windows Server 2016 reaches end of extended support on 12 January 2027. After that date it receives no security patches. Microsoft offers paid Extended Security Updates for up to three years through Azure Arc, but recommends upgrading to Windows Server 2025 or moving workloads to the cloud.
Your options before 12 January 2027
| Option | Best for | Watch out for |
|---|---|---|
| Upgrade to Windows Server 2025 | Servers that must stay on-site | Hardware age and application compatibility |
| Move to Azure or Microsoft 365 | Businesses wanting to retire the server | Line-of-business apps that need a server |
| Extended Security Updates (Azure Arc) | A short bridge while you migrate | Cost rises each year; security fixes only |
| Do nothing | Nobody | Unpatched server, failed Cyber Essentials |
Also on the list for 2027
SQL Server 2017 (12 October 2027), System Center 2016 and BizTalk Server 2016 (11 January 2027) and Visual Studio 2017 (13 April 2027) are close behind. Check them together in our full timeline.
How ABCOM helps
We assess each server, recommend upgrade, cloud move or bridge, and handle the migration. Retiring old servers safely, including secure data wiping, is part of our service: see server decommissioning.
Quick answers
Can I keep running Windows Server 2016 after January 2027?
It will keep running, but without security patches. That exposes your data and can fail Cyber Essentials, so treat any continued use as a short, paid bridge only.
When does Windows Server 2019 end?
Windows Server 2019 reaches end of extended support on 9 January 2029, so plan its replacement within the next couple of years.
Running Windows Server 2016? Talk to us about the cheapest safe route before the January deadline.
Related answers and guides
- Which Microsoft products reach end of life in 2027?
- Microsoft End of Life Dates 2027
- Server decommissioning guide
- Moving to the cloud
- All ABCOM FAQs
Sources and further reading
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