The One-Year Clock Is Ticking: Windows 10 ESU Ends October 2026 — And 'We'll Pay for Another Year' Is a Trap

A manufacturing client in Ilkeston called us in November. They'd bought Windows 10 Extended Security Updates back in October, ticked the box marked 'sorted', and moved on. Then their cyber insurer sent a renewal questionnaire asking for the end-of-life date on every operating system in the business. That's when the penny dropped: ESU isn't a fix. It's a countdown timer with an invoice attached.

Windows 10 reached end of support on 14 October 2025. Microsoft's consumer ESU programme runs for one year. The commercial programme for businesses runs for a maximum of three, and the pricing is built to hurt more every year you stay. For most UK SMEs that deferred, the real deadline isn't some abstract point in the future — it's October 2026, when the cheap year ends and the expensive years begin.

There are still roughly half a billion machines running Windows 10 worldwide. A lot of them are sitting in small businesses that made a perfectly reasonable decision to buy a year's breathing room. That decision made sense in 2025. Repeating it in 2026 usually doesn't. Here's the maths.

How the ESU pricing actually works

The commercial ESU programme is priced per device, and it roughly doubles each year. Year one is around $61 per device. Year two is about $122. Year three is around $244. You pay cumulatively, too — if you skip year one and join in year two, you still owe for year one. Microsoft designed it this way on purpose. ESU is meant to be a bridge, not a home.

Convert that to sterling and add VAT and it looks something like this for a single machine:

• Year one (to Oct 2026): ~£50
• Year two (to Oct 2027): ~£100
• Year three (to Oct 2028): ~£200

Three years of ESU on one device lands at roughly £350 before you've spent a penny improving anything. The machine is still old. It's still slow. It still can't run Windows 11. And in October 2028 the programme simply stops — there is no year four.

Now multiply. A 25-person business with, say, 30 devices (some staff have a desktop and a laptop) is looking at:

• Year one: ~£1,500
• Year two: ~£3,000
• Year three: ~£6,000
• Three-year total: ~£10,500

Ten and a half grand to keep ageing hardware limping along for three more years, ending with nothing to show for it. That number is the trap. 'We'll just pay for another year' feels small in isolation. Strung together, it's the price of a proper refresh — with no asset at the end.

Option two: refresh the hardware

A sensible business laptop suitable for Windows 11 and a few years of service costs £550 to £750. A desktop with a monitor sits in a similar range. Call it £650 a device as a working average, including setup and data migration if you handle it in bulk.

For our 30-device business, a full refresh is roughly £19,500 as a one-off. That's more than a single year of ESU, obviously. But compare it to the three-year ESU total of £10,500 and the picture changes, because the refresh buys you something ESU never will:

• Machines that are actually supported and get security updates
• Hardware that lasts four to five years, so the cost spreads to £4,000–£5,000 a year in real terms
• Faster kit, which quietly claws back time across the whole team
• A clean answer for your cyber insurer and any client security questionnaire

You also don't need to refresh everything at once. Not every Windows 10 machine is a candidate for the bin. Some are three years old, meet the Windows 11 hardware requirements, and can be upgraded in place for free. The honest first step is a hardware audit: how many of your devices can take Windows 11 today, how many can't, and how old the ones that can't actually are.

We ran this for a legal firm in West Bridgford with 40 machines. Twenty-two could upgrade to Windows 11 in place at no cost. Twelve were due for replacement anyway on age. Only six were genuinely 'still fine but incompatible' — and those six were the entire ESU decision. Paying £350 each over three years to keep six machines alive versus £3,900 to replace them made the replacement the easy call once we showed them they'd never get that ESU money back.

Option three: Cloud PC (Windows 365)

There's a third route that suits some businesses very well and others not at all. Windows 365 gives each user a Windows 11 desktop that runs in Microsoft's cloud and streams to whatever device they already have — including that old Windows 10 machine, which becomes a dumb terminal.

Pricing runs roughly £28 to £45 per user per month depending on the spec, so call it £35. For 25 users that's about £875 a month, or £10,500 a year.

That's a chunky annual figure, and over three years it dwarfs a hardware refresh. So why would anyone do it? Because it's operating expenditure not capital, because it moves the security and patching burden onto Microsoft, and because it makes hybrid and remote work genuinely simple. For a business that's growing fast, hires contractors, or has staff constantly switching between locations, the per-user monthly model can be worth the premium. For a stable 25-person office with fixed desks, it usually isn't — a straight refresh is cheaper and simpler.

The decision matrix

Here's how we'd steer an SME that deferred, based on where you actually sit:

If most of your machines can run Windows 11: Upgrade them in place now. It's free. Buy ESU only for the handful that can't, and only for the months you need to sequence their replacement. Don't buy three years of ESU for a machine you'll replace in six months.

If your machines are old and largely incompatible, and you have stable desks: Plan a phased hardware refresh across the next 6 to 12 months. Use year-one ESU as the bridge that keeps you safe while you buy and deploy in batches — not as the destination.

If you have a mobile, growing or contractor-heavy workforce: Model Windows 365 seriously. The monthly cost is higher but the flexibility and reduced management overhead can justify it, and it lets you retire old hardware without buying new kit for everyone at once.

If you're tempted to just renew ESU again: Stop and do the three-year sum. If you'll still be on Windows 10 hardware in 2028 when the programme ends, you're spending real money on a problem that's guaranteed to come back — larger, and with no options left.

The point about October 2026

The reason this matters now, in early 2026, is lead time. A phased refresh done properly takes months: audit, procurement, imaging, migration, testing, staff downtime kept to a minimum. If you wait until September 2026 to start, you'll be rushing exactly the work that goes wrong when rushed — and the year-two ESU bill lands on top.

The businesses that come out of this cleanly are the ones treating October 2026 not as the moment to renew, but as the deadline they're already working backwards from. If you're not sure how many of your machines can make the jump for free, that audit is a short conversation and a much cheaper one than another year of ESU. Get in touch and we'll run your actual numbers before the clock forces the decision for you.