Time-sensitive
Windows Server 2016 support ends 12 January 2027
After that date there are no free security updates, so an old server becomes progressively riskier — especially if it is reachable from the internet. Here are your four honest options.
What “end of support” means. Your server keeps running on 12 January 2027. What stops is security patching — every new vulnerability found after that stays open on your machine. An unsupported, internet-facing server is the most common way small businesses get owned.
Your options
There are only four honest paths
Upgrade to Windows Server 2025
Same role, newer OS. More cost and a migration window, but the straightforward path where the software supports it.
Move to Azure / cloud
Run the workload on a supported cloud instance instead of an ageing on-prem box.
Replace with SharePoint / OneDrive
For plain file shares, Microsoft 365 is often cheaper and simpler than a new server. The honest default for many offices.
Buy time with ESU via Azure Arc
Extended Security Updates keep patches flowing after the cut-off — a stopgap while you migrate, not a permanent plan.
How we help
A fixed-fee Exit Assessment, then a plan you can trust
Migrations slip. The businesses that get into trouble start in November 2026 and hope to cut over in a weekend. We schedule this properly.
- 1
Exit Assessment (fixed fee)
We inventory what the server actually does, who depends on it and what would break — then recommend one honest option.
- 2
Schedule realistically
We plan the move around your busy season and pilot with a small group before cutting everyone over.
- 3
Migrate & decommission
Stand up the new service, move data, test restores, then harden or switch off the old server — not leave it running “just in case”.
The Exit Assessment price is a fixed fee. [CONFIRM Exit Assessment fee]
Frequently asked questions
What actually happens on 12 January 2027?
Microsoft extended support for Windows Server 2016 ends. After that there are no free security updates, so the server becomes progressively riskier to run, especially if it is reachable from the internet.
Can we just buy Extended Security Updates?
ESU through Azure Arc can buy time, but it is a stopgap, not a plan. It suits a migration you are scheduling realistically, not a server you intend to run indefinitely without patching.
Do we have to upgrade to Server 2025?
Not always. Many file shares and applications are better replaced by Microsoft 365 (SharePoint/OneDrive) or a supported cloud instance than by a new on-prem server. The Exit Assessment tells you which option is honest for your software.
Our software only runs on Server 2016. Now what?
Then we isolate it: no internet exposure, hardened configuration, tested offline backups and a documented compensating control set, with a real plan for when the vendor catches up or does not.
Still running Server 2016? Start now.
If your server is internet-facing, this is urgent. Book an Exit Assessment and get a realistic plan in writing.