Network environments
Windows Server 2016 support ends in January 2027: what should a company do with its server?
· 5 min read
In short: Windows Server 2016 leaves extended support on 12 January 2027 according to Microsoft, and security updates stop with it. An SME can upgrade to a newer version, move the server’s tasks to the cloud, or retire the machine if files, accounts and applications already live elsewhere. Deciding this autumn leaves time for a calm changeover.
Many companies of 10 to 100 people still have a server installed in 2017–2019 that has quietly handled files, printing, user accounts and perhaps one industry application ever since. It works, so nobody has touched it. Now it needs to be touched: Windows Server 2016 reaches end of support in January 2027. This article walks through what end of support means in practice, what the options are and how to decide.
What does end of support mean?
Windows Server 2016 follows Microsoft’s fixed lifecycle: five years of mainstream support and five years of extended support, during which security updates still arrive. According to Microsoft’s lifecycle table, extended support ends on 12 January 2027. After that no new security updates are published.
The server does not switch itself off on the day. It keeps running exactly as before, and that is precisely the problem: vulnerabilities found after end of support remain unpatched, and the server typically sits at the centre of the company network, at the junction of files, accounts and remote connections. Beyond security, end of support shows up in insurance and contract terms and in the fact that new software versions no longer support the old platform.
What does the server actually do?
Before comparing options, find out what is on the server. The typical list is shorter than expected: file shares, user accounts and sign-in (a domain), printing, possibly backups and one or two applications installed on the server years ago because it happened to be there.
For each task, record who uses it and whether a replacement already exists. Often the files have migrated to Microsoft 365 over the years, the accounts are in the cloud, and the server only runs one application and printing any more. Then the decision is easier than it looks.
| Option | When | Note |
|---|---|---|
| Upgrade in place | The server has tasks that stay on premises | Its own licence, a full backup first, hardware reviewed at the same time |
| Tasks to the cloud | The tasks are files, accounts and printing | Planned together with the network |
| Retiring the server | Everything already lives elsewhere | Every dependency checked before shutdown |
When is upgrading the server the right choice?
If the server has tasks that stay on premises, it is upgraded to a supported version. According to Microsoft’s guidance, Windows Server 2016 can be upgraded in place directly to Windows Server 2019, 2022 or 2025, and the latest, 2025, is the natural target. The upgrade requires its own licence, and a full backup is taken first.
In practice the hardware should be reviewed at the same time: a server bought in 2017 is ten years old in 2027, and moving to a new version is often best done on new hardware or a virtual machine, with the old server kept in reserve during the move. The same applies to applications: check with the vendor that the software supports the new server version.
When should the tasks move to the cloud?
If the server’s tasks are files, accounts and printing, they move to cloud services without a new server: files to SharePoint and OneDrive, accounts and sign-in to Entra ID, printing to cloud printing. The industry application is the deciding factor: many already have a cloud version, and if not, it can run on a virtual server in the cloud.
A cloud move removes the hardware, the electricity and the backup equipment, but it changes what the network has to do: when all work travels over the internet, the connection and the wifi have to carry it, and the VPN needs of remote workers either disappear or change. The move should therefore be planned together with the network, not as a separate project.
When can the server be retired?
If the survey shows that nothing is left on the server that isn’t already elsewhere, it is shut down in a controlled way. This is more common than you might think. The work lies in checking every dependency before shutdown: scanners that save to a network drive, old accounting archives, printer drivers and the one Excel macro that points to a server path. After shutdown the server is kept in reserve for a while before it is removed and wiped securely.
What about extended security updates?
Microsoft has offered paid Extended Security Updates for previous server versions, for up to three years after end of support and at no extra charge for servers running in its cloud. Microsoft itself describes them as a last resort: they include only critical and important security updates, no new features or other fixes.
If the schedule has already slipped, extended updates buy time, but they do not replace the decision.
How and when is the decision made?
Three steps.
- A survey. What is on the server, who uses it and what is already elsewhere.
- The choice. Upgrade, cloud or retirement, or a combination where files move to the cloud and one application stays on a new server.
- The schedule. The move is done in a quiet period, a backup is taken before every step, and the old server is kept in reserve through the transition.
Autumn 2026 is the right time to start. Four months is plenty for a controlled move, but it should not be left to the December rush and the holidays.
Does your company have Windows Server 2016? See how our network and infrastructure services work, or tell us about your situation and we’ll map the server’s tasks and look together at which option fits.
