Last October, a lot of business owners braced for something to break. Windows 10 hit its official end of support on October 14, 2025, the warnings had been loud for a year, and then… Monday morning came and everything turned on like normal.
That’s exactly why the next deadline is going to sneak up on people.
On October 13, 2026 — about eight weeks from now — the first year of paid Extended Security Updates for Windows 10 runs out. If your business bought that coverage last fall, this is the date your protection lapses. And if you didn’t buy it, you’ve been running unpatched for ten months and probably don’t know it.
Here’s what’s actually happening, in plain English, and what to do about it before the calendar makes the decision for you.
What Already Happened
Windows 10 stopped receiving free security updates in October 2025. Microsoft offered a paid escape hatch called Extended Security Updates, or ESU — a per-device subscription that keeps critical patches flowing while you plan your move.
ESU bought time. It did not fix anything. That distinction matters a lot right now.
Two Different Things Are Ending, and People Keep Mixing Them Up
This is where most of the confusion lives. There are two separate clocks running on your Windows 10 machines, and they have nothing to do with each other.
Clock One: Your Security Patches
Commercial ESU is priced per device, per year, and the price doubles every year on purpose. Year 1 ran roughly $61 per device. Year 2, which starts this October, runs about $122. Year 3 is around $244 — and then the program ends entirely in October 2028.
Microsoft designed that pricing to be uncomfortable. It’s a treadmill that gets steeper every year and dead-ends regardless.
Clock Two: Your Microsoft 365 Apps
This one already happened, and almost nobody noticed. Microsoft 365 apps on Windows 10 are now frozen at Version 2608. Your Word, Excel, and Outlook will keep getting security fixes through October 10, 2028, but they will never get another new feature.
No new Copilot tools. No new ribbon features. Nothing. Your Office install is a museum piece that still gets its locks changed.
And here’s the part that catches people: this freeze applies whether or not you pay for ESU. Buying security updates does not unfreeze your Office apps. You’re paying to stay still.
What Actually Stops Working vs. What Just Stops Improving
Let’s be honest about the risk, because fear-mongering doesn’t help anyone make a decision.
Nothing goes dark on October 14. Your computers will boot. Excel will open your spreadsheets. Your team will get their email. There is no kill switch.
What changes is your exposure. An unpatched Windows machine on your network is a known, published, permanently-open door — and attackers actively scan for exactly that. Meanwhile your staff quietly falls further behind on tools your competitors already have. It’s not a crash. It’s a slow leak in two directions at once.
Your Three Honest Options
Pay for ESU Year 2. Roughly $122 per device buys you until October 2027. It’s the right call for a machine running specialized software that genuinely can’t move yet — a shop floor system, a legacy line-of-business app, a piece of equipment with a controller PC. It is the wrong call for a general office computer, because you’re spending real money to receive zero new capability.
Upgrade in place. If the hardware meets the Windows 11 requirements, the upgrade is free. Most business machines bought in 2019 or later will qualify. This is the cheapest good outcome and it’s worth checking before you assume otherwise.
Replace the machine. For anything five or more years old that fails the compatibility check, this is the real answer. You were going to replace it in the next 18 months anyway. The deadline just tells you which 18 months.
The Math Most Owners Miss
Say you have fifteen Windows 10 machines still in service. ESU Year 2 across all of them runs about $1,830 — for one year, with no new features, no performance gain, and the same conversation waiting for you next October at double the price.
That $1,830 is a meaningful down payment on actual replacements. Once you see the number written down, the decision usually makes itself.
Do This in the Next Two Weeks
This is smaller than it sounds. One focused afternoon covers it for most small businesses.
1. Count them. How many machines in your office are still running Windows 10? Not a guess — an actual number. Most owners are off by three or four in either direction.
2. Check each one for Windows 11 eligibility. Settings → Windows Update will tell you, or your IT provider can pull the whole list in minutes.
3. Sort them into three piles. Upgrade now (free). Replace this quarter (aging or ineligible). ESU for one more year (genuinely stuck on legacy software).
That’s the whole project. The businesses that get burned in October aren’t the ones who chose ESU or chose to replace — they’re the ones who never counted.
Know Your Number Before October
We do this inventory for businesses around Castle Rock and the south Denver metro all the time, and it’s rarely as bad as owners expect. Usually more machines qualify for the free upgrade than anyone guessed, and only a handful genuinely need replacing.
But you want that answer in August, when you have options and time to budget — not in mid-October, when you’re making a rushed purchase because coverage already lapsed.
If you’d like a hand counting and sorting your machines, reach out to Castle Rock Sky. We’ll give you the real number and a plan that fits your budget, whether that means upgrading, replacing, or buying one more year of breathing room.
