If your business still runs Windows 10, here is the good news and the fine print in the same breath. You are probably not stranded. Microsoft stopped supporting Windows 10 on October 14, 2025, but there are now a few ways to keep getting security patches while you move to Windows 11. The catch is that the free option everyone heard about in June 2026 was written for home users, not office fleets. Here is where things actually stand for a Utah business, and how to plan the move without a scramble.
It doesn't mean your computers stop working. It means they stop getting security updates by default. When a new vulnerability is found, and they are found constantly, Windows 11 gets patched and an unpatched Windows 10 machine does not. Attackers know this, and unsupported systems become prime targets for ransomware. Over time, software vendors also drop support for Windows 10, so your business apps and hardware drivers slowly stop working too. The wrinkle in 2026 is that there are now both free and paid ways to keep receiving patches for a while longer, and the difference between them matters a lot for a business.
Extended Security Updates (ESU) are Microsoft's way of keeping critical patches flowing while you transition to Windows 11. There are two separate programs, and they are not interchangeable.
This is the track that made headlines. On an eligible personal machine you can get ESU free by turning on Windows Backup to sync your settings, or for 1,000 Microsoft Rewards points, or a one-time $30 that covers up to 10 devices. It requires Windows 10 version 22H2 and a personal Microsoft account tied to the license. It originally ran a single year to October 2026, but in June 2026 Microsoft quietly extended it, so it now runs through October 12, 2027.
This is the track built for businesses. It is purchased through volume licensing at $61 per device for Year One, and the price doubles every year after, for a maximum of three years. Year One began in November 2025. It is also cumulative, so if you wait and buy in Year Two, you pay for Year One too. Windows 10 virtual machines running on Windows 365 or Azure get ESU at no extra charge.
Here is why this matters beyond convenience. A Windows 10 machine that is neither upgraded to Windows 11 nor properly covered by ESU is, in plain terms, unpatched. An unpatched operating system is exactly the kind of gap that can put you out of compliance with HIPAA, PCI DSS, and the FTC Safeguards Rule, and it can fail the security attestations your cyber insurance carrier now requires. The free consumer extension does not change that math for a business, because if it does not apply to your managed machines, those machines are still unpatched. The goal is not "still getting updates somehow," it is every machine either on Windows 11 or genuinely covered.
The businesses that handle this well don't do it in a panic. They:
Done right, most of your team barely notices. They sit down to a familiar, faster, more secure machine.
You are likely not stranded. Between the extended consumer program and commercial ESU, there are ways to keep Windows 10 patched into 2027. But do not assume the free headline covers your business machines, and do not let breathing room turn into a reason to put off a real Windows 11 plan. The smart move is to figure out where each device stands now, while you can do it calmly and on budget. If you'd like a device-by-device compatibility check and a migration plan sized to your business, that's exactly what our free assessment covers.
We'll check every device for compatibility and map out a phased migration with minimal downtime.
Get a Free IT Assessment