Windows 10 ESU Year Two: How to Decide What Technology to Carry Into 2027

Every office has a few technology habits that nobody chose on purpose. A computer takes ten minutes to start, so its owner makes coffee while it loads. A spreadsheet copies data between two systems that were never connected. A device still runs an old operating system because it hosts one application nobody wants to touch.

These habits are easy to overlook because the people who live with them have learned to work around them. The end of the year is a good time to look at them again, and this year there is a specific reason to start with Windows 10.

In October, Microsoft's Extended Security Updates (ESU) program for Windows 10 entered its second year, and the price per device doubled. For any business still running Windows 10, the decision to renew, replace or retire those devices now carries a higher cost. This guide explains where Windows 10 stands, how to decide what to keep, and how to plan the change without disrupting the business.

Where Windows 10 stands this fall

Microsoft ended support for Windows 10 on October 14, 2025. Since then, organizations can keep receiving security updates only through the paid ESU program. Microsoft set the first-year price at $61 per device and doubles it every year, for a maximum of three years. That puts the second year at $122 per device.

ESU is also cumulative. According to Microsoft, an organization that joins in year two must pay for year one as well. A device enrolling now therefore costs $183 to cover through the current year. For a business with 20 Windows 10 computers, that is $3,660 to keep the same machines secure for one more year, with no new features and no performance improvements.

Windows 10 is still common. Statcounter data reported in October 2026 showed it running on about 28 percent of Windows computers worldwide. Many of those devices sit in businesses that postponed the upgrade because the computers still worked.

Three questions for every aging device

Is it still supported?

An unsupported operating system stops receiving security fixes, which leaves known vulnerabilities open. Cyber insurers and auditors regularly ask about unsupported systems, and a single unpatched computer with access to email or client files can become the entry point for an attack. Support status is the first filter.

Does it work well, or does it only work?

A device can turn on every morning and still slow the business down. Ask how much time employees lose waiting for it, whether it struggles with the applications they use every day, and whether people have built workarounds to avoid its limitations. "It still works" is a low standard for a tool someone depends on for eight hours a day.

What does it cost to keep?

One repair is rarely a reason to replace a device. Repeated repairs are different. Add up the support time, the hours employees spend waiting and the ESU fees. When those costs approach the price of a replacement, keeping the old device stops being the economical choice.

Look for the workarounds nobody questions anymore

Windows 10 devices are easy to find with an inventory report. Workarounds are harder to find because they live in people's routines. Someone enters the same customer details into two systems. A shared spreadsheet tracks something the software was supposed to track. A printer only works from one computer.

The simplest way to find them is to ask your team one question: what technology problem have you learned to live with? The answers often point to projects that belong in next year's plan, and some of them can be fixed in an afternoon.

How to plan the transition

Replacing devices across a business works best as a scheduled project. A practical plan includes these steps:

• Build an inventory that lists every device, its operating system, its age and the person who uses it.
• Check which devices meet the hardware requirements for Windows 11. Some can be upgraded in place, and others need to be replaced.
• Prioritize by risk. Devices that handle client data, payments or administrative access should move first.
• Use ESU only as a bridge for devices that cannot be replaced right away, such as a computer running specialized software that is waiting on a vendor update.
• Spread replacements across quarters so the cost and the workload stay manageable.
• Plan data migration, user setup and the secure disposal of old devices, including wiping or destroying their drives.

A plan like this turns one large, uncomfortable decision into a series of small, predictable ones.

What proactive IT looks like

The best time to deal with an unsupported system is before it shows up in an audit, an insurance questionnaire or an incident report. A proactive IT partner monitors device health and support status continuously, flags devices that are approaching the end of their life, and brings recommendations to you before you have to ask.

KairosIT clients mention this in their reviews. One client described a KairosIT technician this way:

"He always makes recommendations to improve security and efficiency, which I consider very valuable."

Blanco A., Google review

Another client, interviewed by Clutch, explained that the KairosIT team set up a security review on its own initiative because the two companies had not discussed security in a while. This kind of attention is what clients mean when they say a provider catches things before they become problems.

Carry forward only what still serves the business

Not every old device needs to go. Some equipment still does its job well and has years of support left. The goal of an end-of-year review is to make sure each piece of technology stays because it serves the business, and that the replacements you do need happen on a schedule you control.

If you are deciding what to do with your Windows 10 devices, or with any technology your team has outgrown, our team can help you weigh the options and plan the change. Contact us to talk it through.