Windows Server 2016 Support Ends January 12, 2027: What to Do Now

Microsoft's lifecycle page lists the end of extended support for Windows Server 2016 as January 12, 2027 (the listing closes at 6:59 a.m. Pacific on January 13). After that date Microsoft stops shipping security updates for it. That covers every edition: Standard, Datacenter, Essentials and MultiPoint Premium.

If your office has one server, there is a decent chance it is a 2016 box. It was the current version from late 2016 until Windows Server 2019 arrived, and a lot of small businesses bought a server in that window and never touched it again. It runs the shared drive, the sign-ins, the printers, and often the accounting or practice software that everyone depends on.

What Actually Changes on January 13

Nothing you can see. The server boots, the shared drive opens, people print. Three things change underneath:

• No more security fixes. Any flaw found after that date stays open on that server. Attackers know this and keep scanning for old versions for years.
• Software vendors start leaving. Antivirus, backup and line-of-business vendors drop support for operating systems Microsoft no longer supports. Microsoft's own Office apps are already on that path: support for Microsoft 365 Apps on Windows Server 2016 ended October 14, 2025, with security updates for them continuing only until October 10, 2028.
• Insurance and compliance get harder. Cyber insurance applications and audits ask whether you run unsupported systems. "Yes, the main server" is a hard answer to give.

Microsoft's own notice is short: it recommends upgrading to the latest version of Windows Server.

Check the Software on the Server, Too

The operating system is not the only thing aging out. Two common passengers on a 2016 server have their own dates:

• SQL Server 2016, which sits under a lot of accounting, dental, legal and manufacturing software, left extended support on July 14, 2026. If your vendor's software installed it, ask them which newer SQL version they support before you plan the server move.
• Exchange Server. If the same box still runs your email, that is a separate and more urgent problem. Our post on planning a move off Exchange walks through it.

Your Options, Honestly

1. Upgrade the server in place

Microsoft's guidance notes that starting with Windows Server 2025, non-clustered in-place upgrades can jump up to four versions, so 2016 straight to 2025 is supported. It is the fastest path when the hardware is still healthy and under warranty. It is a poor fit for a server that is eight or nine years old, because you end up with a new operating system on old disks and an old power supply.

2. Replace it with a new server or virtual machine

Build the new server next to the old one, move the shares, sign-ins and applications across, then switch over on a weekend. This is the most common answer for a small office, because the hardware is due anyway and the old server stays available as a fallback until you are sure.

3. Move some roles off the server entirely

If you already pay for Microsoft 365, the shared drive can often move to SharePoint or OneDrive, and sign-ins can move to Microsoft's cloud. Some offices find they only needed the server for one application. This takes more planning, but it can mean buying a smaller server, or none.

4. Buy Extended Security Updates, if you qualify

Microsoft does sell extra years of security fixes for 2016. Per Microsoft's Azure Arc documentation, they cover critical and important security updates for up to three years, through 2030. The catches matter for a small business:

• They are delivered through Azure Arc, which means connecting the server to Microsoft Azure and paying monthly.
• Only the Standard and Datacenter editions are supported. Essentials is not.
• Buying them needs Software Assurance through a volume licensing program, or licensing through SPLA or a Server Subscription. A server bought with a one-time license usually does not qualify.
• Billing starts January 13, 2027, and the updates include no new features or non-security fixes.

Treat ESU as a bridge to finish a migration that is already underway, not as a plan.

5. Keep it, and lock it down

Sometimes one old application has to stay on 2016 a while longer. If so, take that server off the internet, put it on its own network segment that only the machines that need it can reach, and keep a tested backup. Our post on unpatched systems and flat networks explains why that isolation matters.

A Checklist You Can Start This Week

1. Confirm the version. On the server, run winver. It names the Windows Server version and edition. Write down the edition, because it decides your ESU options.
2. List what the server does. Shared folders, sign-ins (Active Directory), DNS and DHCP, printers, scanned-document folders, and every installed program. Ask each department what breaks if the server is off for an hour.
3. Call your software vendors. Ask which Windows Server and SQL Server versions they support now, and whether they help with the move. Their answer often sets your timeline.
4. Check the hardware. Look up the purchase date and warranty. A server past warranty is a replacement, not an upgrade.
5. Check your licensing. Find out whether you have Software Assurance. If not, plan as if ESU is not available to you.
6. Test a restore. Before anything moves, prove you can bring back a folder from last week's backup.
7. Pick a cutover weekend and work backward: hardware order, build, data copy, testing.

When to Call Someone

Plenty of offices can do the first five steps on that list themselves. It is worth bringing in help when:

• The server handles sign-ins for the whole office. Moving Active Directory badly locks everyone out.
• Nobody knows the admin passwords, or the person who set it up has left.
• A line-of-business application runs on it and the vendor wants a technical contact.
• You also have Windows 10 computers or an old Exchange server to deal with in the same budget year.

We do this work for offices in Canton, Akron, Cleveland and the rest of Northeast Ohio. If you want a second opinion on your plan, call (330) 305-2750. If you'd rather we take ongoing care of the server itself, see our server protection plan.

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