Two Microsoft support deadlines fall on October 13, nine days from now, and between them they catch most of the ways a small business ends up running something unsupported. The first will surprise people, because it affects machines that already upgraded to Windows 11.
Deadline one: Windows 11 version 24H2 Home and Pro
Per Microsoft's own support matrix, Windows 11 version 24H2 reaches end of updates on 2026-10-13 for the Home, Pro, Pro Education and Pro for Workstations editions. Those are the editions small businesses actually run. The Enterprise, Education and IoT Enterprise editions of the same version get another year, until 2027-10-12, which is why this one gets missed: the advice circulating in larger organizations does not apply to you.
If you are on 24H2 Pro, you have nine days before that machine stops receiving security updates. The fix is a version upgrade, not a new computer: Windows 11 version 25H2 is supported to 2027-10-12 for Home and Pro, and version 26H2 became generally available on September 29, taking Home and Pro to 2028-10-10. Checking which version you are on takes a few seconds: Settings, System, About, and read the version field, or run winver.
Deadline two: Windows 10 commercial ESU year one
Windows 10 itself reached end of updates on 2025-10-14. Businesses that were not ready bought Extended Security Updates to bridge the gap, and year one of commercial ESU ends October 13, 2026. The decision now is year two, and the pricing is designed to make you move: roughly 61 US dollars per device for year one, 122 for year two, and 244 for year three. It is also cumulative, meaning a business that skipped year one cannot start at year two.
Doubling per year is not an accident, it is a nudge. At year two pricing, a few years of ESU on an aging fleet approaches the cost of replacing the machines, without any of the benefits. Worth adding: Windows 10 Enterprise LTSB 2016 also reaches end of extended support on 2026-10-13, which catches a handful of long-lived industrial and point-of-sale installs.
How to decide, quickly
- Inventory by version, not by age. You need the Windows version string for every machine. A five-year-old laptop on 25H2 is fine; a one-year-old laptop on 24H2 Pro is not.
- Upgrade the ones that can. Any device already on Windows 11 24H2 can move to 25H2 or 26H2 through Windows Update. This is the cheap pile and it is usually the biggest.
- For Windows 10 machines, check hardware eligibility before paying for ESU. Many can take Windows 11 and nobody has tried.
- Only buy ESU year two deliberately, for machines with a real reason: an application that will not run on Windows 11, a certified device, or a replacement already budgeted for a specific quarter.
- Watch for the stragglers: the reception laptop, the warehouse terminal, the machine running the one piece of software nobody wants to touch. These are always what is left unsupported.
- Put the next dates in the calendar now. 25H2 Home and Pro ends 2027-10-12. ESU year two ends 2027-10-12. The pattern is every October, so treat it as an annual review rather than a recurring surprise.
What this means for your business
Unsupported Windows is not an abstract compliance ding. It is a machine that stops receiving fixes for flaws attackers are actively using, sitting on the same network as your files, and it will eventually show up as an exclusion on a cyber insurance application or a failed answer on a client security questionnaire. The work here is genuinely small: get the version list, upgrade everything that can be upgraded, and make a conscious call on the rest. The businesses that get hurt by these dates are not the ones that decided to pay for ESU, they are the ones that never found out what they were running. This is the same lesson as the EWS cutoff last week and the Windows 10 deadline before it: these are inventory tests wearing deadline clothing.