Windows Server 2016 extended support ends on 12 January 2027. After that date it gets no security updates unless you pay for Extended Security Updates through Azure Arc. There are four routes: a new server, Microsoft 365, Azure, or buying time with ESU.
What ends
Microsoft’s extended support for Windows Server 2016 ends on 12 January 2027. After that, the server receives no security updates unless you buy Extended Security Updates, which Microsoft offers through Azure Arc. It will keep running; it just stops being fixed.
What probably runs on it
In a small business, one 2016 server often does several jobs at once. List them before choosing a route:
- Sign-in and permissions (Active Directory).
- File shares.
- A line-of-business application and its database.
- Printing, and sometimes remote desktop for staff.
The four ways out
| Route | Suits | Watch for |
|---|---|---|
| A new server | Applications that must run on site, and offices with slow internet | Hardware lead times, and planning the migration properly |
| Microsoft 365 | File shares and sign-in, moved to SharePoint, OneDrive and Entra ID | Folder permissions and very large files |
| Azure | Applications that need a server but not one in the building | Monthly running costs and the internet connection |
| ESU through Azure Arc | Buying time for a server that can’t move yet | It’s a bridge, not a destination |
Most small businesses end up combining two: files and sign-in to Microsoft 365, and the one application that needs a server to a new one or to Azure.
A timeline that finishes before the date
- October: inventory what runs on the server and who depends on it.
- November: choose the route for each job, and order anything with a lead time.
- December: build and test, with a restore point first.
- Early January: cut over in a quiet window, well before the 12th.
Source: Microsoft Windows Server blog, planning ahead for Windows Server 2016 end of support, 25 Feb 2026.
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