Managed IT · Windows
What end of support means for a business in 2026, what Extended Security Updates cost, and how to finish the move to Windows 11.
What stopped on October 14, 2025
ESU cost and the Year 2 jump
A five-step upgrade plan
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Microsoft ended support for Windows 10 on October 14, 2025. Windows 10 computers still turn on and run, but they no longer get security fixes, bug fixes or technical support unless they are enrolled in the paid Extended Security Updates (ESU) program. For businesses, ESU costs $61 per device for the first year, doubles each year, and runs for a maximum of three years, ending in October 2028. As of October 2026, Year 2 of ESU is starting, so the price per device is rising. The right plan for most businesses is to upgrade capable machines to Windows 11, replace the ones that cannot run it, and use ESU only as a short bridge for the stragglers.
According to Microsoft, after October 14, 2025 Windows 10 no longer receives:
The last feature update was version 22H2. Without security fixes, every newly discovered Windows flaw stays open on those machines. CISA’s Known Exploited Vulnerabilities catalog shows how quickly attackers use published Windows flaws, which is why an unpatched computer becomes riskier every month.
There is also an insurance and compliance angle. Many cyber-insurance applications ask whether you run unsupported operating systems, and regulated businesses may have to show that systems receive security updates. This is general information: check your policy and your obligations with your insurer or counsel.
None of this patches Windows itself. Updated apps on an unpatched operating system are still exposed.
Microsoft’s ESU program delivers critical and important security updates to enrolled Windows 10 devices. Key points from Microsoft’s documentation, as of 2026:
A device joining ESU now pays for two years at once, $183 before Year Three. That is often a meaningful share of a new entry-level business laptop, which is why ESU makes sense only for machines with a firm replacement date or a specific dependency.
Microsoft includes ESU at no additional cost for Windows 10 virtual machines in Windows 365 and Azure Virtual Desktop, and says Windows 10 devices connecting to Windows 365 Cloud PCs are entitled to ESU for up to three years with an active Windows 365 license. For a business with a handful of old machines and staff who mostly use a browser and Microsoft 365, Cloud PCs can be a tidy bridge. For most offices, replacing the hardware is simpler.
Not sure how many Windows 10 machines you still have, or which ones can upgrade? Our free Technology Health Assessment takes 30 minutes of data collection and gives you a plain-language report the next day, including IT operations and cybersecurity ratings and a short list of next steps in order.
For each machine moving from Windows 10 to Windows 11 in place:
Split the cost into three lines. First, labor for in-place upgrades on eligible machines, which is usually modest per device when done in batches. Second, replacement hardware for machines that cannot run Windows 11, spread across quarters if cash flow is tight. Third, ESU for the few devices that must wait, priced at the cumulative Year One plus Year Two rate. Comparing the second and third lines device by device usually makes the decision obvious.
JLB USA provides managed IT for businesses with roughly 25 to 100 employees, including computer upgrades and replacement planning. For a standard new-computer build, see our new office IT setup checklist, and see our cybersecurity services for patching and endpoint protection.
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October 14, 2025. Since then, Windows 10 receives no security updates, bug fixes or technical support unless the device is enrolled in the paid Extended Security Updates program.
Microsoft lists $61 per device for Year One, doubling each year for up to three years. ESU is cumulative, so joining in Year Two means paying for Year One as well.
The computers will keep running, but they no longer receive security fixes, which raises the risk of compromise and may affect insurance or compliance answers. Upgrade or replace them as soon as practical.
Microsoft says Microsoft 365 apps on Windows 10 will get security updates until October 10, 2028, but Windows itself is not patched without ESU, and support will ask you to move to Windows 11.
Replace it, or as a short bridge enroll it in ESU or move the user to a Windows 365 Cloud PC. Set a retirement date for every machine you bridge.