Windows Server 2016 End of Support: Your Options Before January 12, 2027
Microsoft ends extended support for Windows Server 2016 on January 12, 2027. After that, a 2016 server stops getting security updates unless you pay for them. It keeps running just like before, and that’s the problem. Nothing breaks on January 13, so it’s easy to put off while the server quietly becomes the easiest way into your network.
If you have one, you’ve got three real options: upgrade it, replace it, or pay for more time.
First, find out what you have
Check every server, including the ones nobody thinks about: the one in the closet that runs the door badges, the virtual machine holding an old accounting database, the box a vendor installed years ago and still logs into. Typing winver into the Start menu shows the version.
For each 2016 server, write down what it does, whether the software on it supports a newer version of Windows Server, and how old the hardware is. Those three answers decide the rest. A file server and an old manufacturing app whose vendor went out of business are very different problems.
Upgrade it
Windows Server 2025, Microsoft’s current version, can upgrade a standalone 2016 server in place. That keeps the server’s settings and applications, so it’s the least disruptive path. It’s also the riskiest if you skip the homework. Confirm your applications support the new version, take a full backup and test restoring it, and check that your hardware and licenses carry over.
If the hardware dates from 2016 or 2017, an upgrade puts a new operating system on old equipment. That might buy you a year or two. It usually isn’t the best use of the money.
Replace it
Building a new server and moving the work over is slower, and it’s cleaner. You start on current hardware or a fresh virtual machine, you leave years of leftover settings behind, and you can test before anyone depends on it.
It’s also a good moment to ask whether the server needs to exist at all. Shared files and email may already have a home in Microsoft 365. Line-of-business applications and databases often still belong on a server. Decide one workload at a time rather than all at once.
Pay for more time
Microsoft sells Extended Security Updates for Windows Server 2016, with security fixes for up to three more years. Treat it as a bridge while you finish moving, not a way to stay put.
There are two catches. Each server has to connect to Microsoft’s Azure Arc service, and you need the right licensing: Software Assurance through a Microsoft volume licensing program, or an equivalent subscription. If your server license came with the hardware or from a store, check whether you qualify before you plan around this. Microsoft doesn’t publish the price, so ask your licensing reseller.
Other software from the same era
If a 2016 server also runs SQL Server 2016, that reached end of support in July 2026, so plan both upgrades together. And if you still run your own Exchange Server 2016, it has been without security updates since October 2025.
A timeline that still works
January 12 is less than three months away, with the holidays in the middle. Here’s a realistic order:
- Now: list every 2016 server and what it does, and ask your software vendors about Windows Server 2025.
- Next few weeks: pick a path for each server. If you’re counting on Extended Security Updates, confirm your licensing qualifies.
- Before the holidays: order hardware and licenses, and test the backups you’ll rely on during the move.
- Early January: finish the moves you can, and enroll the rest in Extended Security Updates.
If a server can’t move in time, shrink what it can reach. Take it off the internet if it doesn’t need to be there, limit who can sign in, and keep a closer eye on it. An unpatched server that nothing else can reach is a much smaller problem than one sitting in the middle of everything.
If you’d like help working out the right path for each server, tell us what you’re running. Upgrades and migrations like this are project work we run for clients alongside our managed IT and co-managed IT services.
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Questions this post answers
When does Windows Server 2016 support end?
Microsoft ends extended support for Windows Server 2016 on January 12, 2027. After that, a 2016 server stops getting security updates unless you pay for them. It keeps running just like before, which is why it’s easy to put off.
What are the options for a Windows Server 2016 machine?
Three: upgrade it, replace it, or pay for more time. Windows Server 2025 can upgrade a standalone 2016 server in place, which keeps its settings and applications. Building a new server and moving the work over is slower, and it’s cleaner. Microsoft also sells Extended Security Updates with security fixes for up to three more years, as a bridge while you finish moving.
Who can buy Extended Security Updates for Windows Server 2016?
You need the right licensing: Software Assurance through a Microsoft volume licensing program, or an equivalent subscription. Each server also has to connect to Microsoft’s Azure Arc service. If your server license came with the hardware or from a store, check whether you qualify before you plan around this. Microsoft doesn’t publish the price, so ask your licensing reseller.
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