If your business still runs Windows 10, there’s a good chance some of your computers stopped getting security updates last month. Nobody sent you a warning. The PCs still turn on, open email and print invoices like nothing happened.
That’s what makes this one easy to miss.
To add to the confusion, Microsoft quietly gave home users another free year of Windows 10 updates earlier this year. A lot of business owners read that headline and assumed it covered them too. It doesn’t.
Here’s what actually changed, how to check your own machines in a few minutes, and what we’d recommend doing about it.
What Changed on October 13, 2026
Regular support for Windows 10 ended back on October 14, 2025. Since then, the only way to keep receiving security fixes has been Microsoft’s Extended Security Updates program, or ESU for short.
For businesses, ESU is sold one year at a time. Year one ended with the October 13, 2026 updates. If your company paid for year one and didn’t renew, those PCs are now on their own. If you never enrolled at all, they haven’t had a security fix in over a year.
Microsoft’s next monthly round of security fixes lands on Tuesday, November 10. Any business PC that isn’t enrolled in year two won’t receive it.
“But I Read Windows 10 Got Another Free Year”
You did, and it’s true, just not for most businesses. In June 2026, Microsoft extended its free consumer ESU program to October 2027. That extension is meant for personal computers signed in with a personal Microsoft account.
Computers joined to a company domain, joined to Microsoft Entra ID (what used to be Azure AD), or managed through a device management tool like Intune are not eligible. In other words, if your IT is set up properly, your work PCs fall under the business rules, not the home ones.
How to Check Your Own PCs in Five Minutes
You don’t need to be technical for this. On each Windows 10 computer:
- Open Settings, go to Update & Security, then Windows Update.
- Click View update history and look at the date of the most recent security or cumulative update.
- If the newest one is from October 2026 or earlier, and November’s updates don’t show up after November 10, that PC is no longer protected.
Write down every machine that’s still on Windows 10, who uses it and roughly how old it is. That list is the starting point for every decision below.
Your Three Realistic Options
1. Pay for year two of ESU. This buys time, not a solution. The per-device price doubles each year, and if you skipped year one you have to pay for it as well before year two will activate. Year three, ending in October 2028, is the last one Microsoft will sell. It makes sense for a handful of machines running software that can’t move yet.
2. Upgrade to Windows 11. If a computer meets Windows 11’s hardware requirements, this is usually the best move. The upgrade itself is free. The real work is checking that your line-of-business apps, printers and scanners all behave afterwards, and doing it outside business hours so nobody loses a day.
3. Replace the hardware. Many PCs bought before 2018 simply can’t run Windows 11. For those, paying for extended updates every year is throwing good money after bad. Replacing them in planned batches, rather than all at once, spreads the cost and keeps disruption low. Some businesses turn this into a predictable monthly cost with a hardware as a service arrangement.
What an Unpatched PC Actually Risks
It’s tempting to think one old computer in the back office doesn’t matter. The trouble is that attackers read Microsoft’s monthly security notes too. Every time a flaw is fixed for paying customers, criminals learn exactly where to look on the machines that didn’t get the fix.
That one PC is connected to the same network as your file server, your accounting software and your email. Ransomware rarely stays on the machine it lands on. And if you ever need to make a cyber insurance claim, an insurer asking whether your systems were supported and patched is a very uncomfortable conversation when the answer is no.
If your business handles health, legal or financial information, running unsupported software can also put you on the wrong side of your own privacy obligations.
A Simple 30-Day Plan
- Week 1: Build the inventory above and mark each PC as “can upgrade”, “needs replacing” or “must stay on Windows 10 for now”.
- Week 2: Buy year-two ESU only for the machines in that last group, and confirm the updates install.
- Week 3: Test Windows 11 on one or two computers with your everyday software before rolling it out to everyone.
- Week 4: Upgrade the rest after hours and set a replacement schedule for the older hardware.
If you want the background on what Windows 11 changes for your team, our Windows 11 guide is a good place to start.
How we help
This is exactly the kind of project that drags on when it lands on a busy owner’s desk. We check every device, tell you plainly which ones are worth upgrading, handle ESU licensing where it makes sense, and do the upgrades after hours with your software tested first. Once you’re on Windows 11, our managed IT services keep every machine patched automatically, so a deadline like this never sneaks up on you again.
If you’re ready to take control of your IT strategy, schedule a 30-minute call to see how we can help.
Every day without a clear IT plan can lead to missed opportunities and increased risk. Now is the time to put the right strategy in place and ensure your technology is working for you, not against you. If you would like to learn how the IT professionals at SinghIT can support your business and help your business grow with confidence, contact us today at (437) 880-2051.