Josh DargieInfrastructure · Cloud · Software

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Windows 10 Just Got Another Year. Now What?

Microsoft quietly pushed free consumer security updates for Windows 10 out to October 2027, but the reprieve does not cover every machine in your office.

Windows 10 stopped being supported in October 2025. Most people I talk to know that part. What a lot of them have not heard is that in June of this year, without much announcement, Microsoft pushed the free consumer extension out by another twelve months, to October 12, 2027.

If you have been quietly dreading a hardware bill this fall, that is good news. It is also the kind of good news that gets misread, because the extension does not apply evenly, and the machines it leaves out tend to be the ones sitting in offices.

Who actually got the extra year

The free extension is the consumer program. To qualify, a PC has to be running Windows 10 version 22H2, fully patched, with an administrator signed in using a Microsoft account. You enrol one of three ways: at no cost by syncing your PC settings to that account, by spending 1,000 Microsoft Rewards points, or with a one-time payment of about $30 USD, which lands somewhere in the low forties in Canadian dollars once currency and tax are applied.

Here is the part that catches small businesses. Machines joined to an Active Directory domain, joined to Microsoft Entra, or managed through an MDM are excluded. Entra-registered devices are fine, but domain-joined and MDM-managed ones are not.

So the small office running a handful of workgroup laptops with nobody managing them centrally gets a free year. The slightly more organized shop that set up a domain or rolled out device management, which is to say the one doing things properly, is on the commercial track instead.

What the commercial track costs

Business ESU is sold per device, per year, and the price doubles each year: roughly $61 USD for year one, $122 for year two, and $244 for year three, with a maximum of three years and each year cumulative. Buy into year two and you are paying for year one as well. Over the full three years it works out to about $427 USD per device, and it ends in October 2028 regardless.

That escalator is deliberate. It is priced to make standing still uncomfortable, and past a certain number of machines it stops competing with just buying new hardware.

Two useful exceptions: Windows 10 running on Azure or Windows 365 gets ESU at no extra charge, and if you have some odd machine that genuinely cannot move (a PC bolted to a piece of equipment, say), a virtual desktop is sometimes a cheaper answer than a licence.

Security updates are not the same as support

Whichever track you land on, be clear about what you are buying. ESU is security patches. No new features, no bug fixes, no new driver support, no help when something breaks.

More to the point, Microsoft is not the only vendor with an opinion. Browser makers, accounting packages and line-of-business software all drop old operating systems on their own schedules, and none of them are waiting for October 2027. In practice, what forces the upgrade is rarely Windows itself. It is usually a supplier portal that stops working in an unsupported browser on a Tuesday morning.

What to do with the extra year

An extra year is only worth something if you spend it on a plan instead of forgetting about it until next August.

Start with a list. Every Windows machine, its age, whether it meets the Windows 11 requirements (mostly TPM 2.0 and a supported processor), and whether it is domain-joined or managed. That last column tells you which machines got the free year and which did not. Most offices I look at have never had this list, and building it takes an afternoon.

Then sort into three piles. Machines that can take Windows 11 and should be upgraded on a schedule you choose. Machines that cannot, and need replacing over the next twelve months rather than all at once in a panic. And machines that could simply go away, because nobody has logged into them in a year and nobody will admit to owning them.

You will see advice online about forcing Windows 11 onto unsupported hardware. It works, in the sense that it installs. It also puts you in an unsupported configuration that Microsoft can break at any update, on a machine you rely on to run the business. For a home spare, fine. For anything with your invoices on it, no.

If replacing a batch of machines means someone has to physically deploy them, my company RelayPoint Technologies handles that kind of work across Southern Ontario. If you would rather start with the list and the plan, that is what a technology assessment is: a proper inventory, a straight answer on what has to move and when, and a budget spread across the year instead of a single unpleasant quarter.

I do not resell hardware or licences, so I have no reason to tell you to replace more than you need to. Get in touch if you want a second set of eyes on the list before you start spending.

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