Windows Server 2016 extended support ends on 12 January 2027. If your company still uses it, now is the time to decide what happens to those systems. www.microsoft.com
Some servers may be straightforward to upgrade. Others might run an older application that needs an update of its own, or a service that nobody has reviewed for years.
That is why it helps to start before the upgrade window is booked. You need time to speak to suppliers, check the software and agree with the business on when the change can happen.
Here is how we would approach it.
Find out which services still rely on it
Start with a list of your Windows Server 2016 machines, then add what each one actually does.
A server name alone will not tell you whether it supports invoicing, stores shared documents or runs a process the warehouse needs every morning. Include the people who use the service and the person responsible for it.
You may also find machines that are no longer needed. Confirm that before retiring them, including any data you need to keep.
The aim is to understand the work involved. Ten servers running the same application may need a very different plan from ten servers supporting ten separate business processes.
Speak to the application supplier early
If a server runs business software, ask the supplier which newer Windows Server versions it supports and whether the application needs upgrading first.
Get a clear answer about the version you actually use. A supplier supporting its latest release on Windows Server 2025 does not necessarily mean your older release is supported too.
Check any connected databases, integrations and backup tools as part of the same review.
These conversations can affect the budget and schedule. Finding out now that an application needs additional work gives you more options than discovering it during the planned server upgrade.
Choose the approach that fits the workload
Microsoft supports several routes to a newer Windows Server version. Depending on the setup, you may be able to upgrade the existing machine or move its services to a new one. Some server roles have specific requirements. learn.microsoft.com
A new server can give you room to install and test an application before users move across. An in-place upgrade may be suitable where the configuration and software support it.
There may also be a reason to change where the service runs, including moving to Azure. Treat that as a decision about the application’s requirements, costs and ongoing management.
Give each workload an agreed approach, an owner and a realistic date.
Use extra time with a clear purpose
If a workload cannot be moved before January, check whether it qualifies for Extended Security Updates.
Microsoft offers eligible Windows Server 2016 systems Critical and Important security updates for up to three years after end of support, including through Azure Arc. These updates do not add new features or solve general application compatibility problems. learn.microsoft.com
This can give you time to complete a longer transition. Agree on what needs to happen during that period, who will do it and what the arrangement will cost.
Keep the remaining work visible so that renewing security coverage does not become the only action taken.
Check that people can do their jobs afterwards
Before the change, agree on how you will test the result.
For a finance application, that might include opening records, producing reports and completing an export. For a file server, it could mean checking access, permissions and the applications that use its shares.
Include scheduled work that runs overnight or at month-end. Confirm monitoring and backup coverage, and prepare a recovery approach before making production changes.
The project is ready to close when the agreed business tasks work, the checks are recorded and the team knows how to manage the updated environment.
Hopp Solutions helps internal IT teams assess existing infrastructure, plan Windows Server migrations and validate the services that depend on it.
Discuss your Windows Server migration with our team.
