Windows 10 Support Ends October 14: Your Four Options

There’s a date on your calendar you didn’t put there. On October 14, 2025, Windows 10 stops receiving security updates. Every PC in your office running it will start up the next morning and work exactly as it did the day before. That’s what makes this easy to put off.

It isn’t an emergency. It’s a decision, and a better one to make in September than in a November scramble.

Update (August 2026): The deadline below has passed, and Microsoft has since extended the consumer Extended Security Updates program by a year, through October 12, 2027, with enrolled devices carried over automatically. That doesn’t help work PCs: consumer ESU still can’t be used in commercial scenarios, and the paid business program is still capped at three years. The decision tree below is unchanged. You just have less runway.

Key takeaways:

• Unsupported doesn’t mean broken. It means every flaw found from October 15 onward stays open on that machine permanently.
• Your first job isn’t picking an option. It’s building a list: which PCs run Windows 10, and which of those can take Windows 11.
• A PC that fails the Windows 11 hardware check is usually old enough that replacing it beats paying to keep it alive.
• Extended Security Updates are a bridge with a toll that doubles every year, and the cheap consumer version isn’t sold for business machines.

Start with a list, not a decision

You can’t price this until you know how big it is. Two questions per machine.

Is it running Windows 10? Settings, then System, then About. Version 22H2 is the only version still getting updates, and the only one eligible for anything after October.

Can it run Windows 11? Microsoft’s free PC Health Check app answers that in seconds. Most of the Windows 11 requirements are undemanding: a 64-bit processor at 1 GHz with two or more cores, 4 GB of memory, 64 GB of storage. The one that catches businesses out is TPM 2.0 with UEFI Secure Boot, a small security chip whose arrival split business PCs into a “before” and an “after” around 2017 and 2018. Older machines usually fail.

More than a handful of computers? Don’t do this by clipboard. Management tooling inventories the whole office in an afternoon, which is a quiet benefit of managed IT: the list exists before the deadline does.

Why “it still works fine” is the wrong test

A five-year-old laptop that boots quickly and runs Word is fine by the only test most owners apply. That test measures whether the machine does its job today, not the risk it carries tomorrow.

Flaws get found in software constantly. While a product is supported, the vendor ships a patch and the gap between found and fixed stays narrow. After end of support the finding continues and the fixing stops, so a weakness discovered in November 2025 is still there in 2027, publicly documented, on a machine that will never get the fix. Microsoft is blunt about it on its Windows 10 end of support page: the software keeps working, and the PC becomes more vulnerable to viruses and malware.

Compliance requirements and cyber insurance renewals ask a version of the same question: is the software you run still supported by its maker? There’s no honest way to answer yes with Windows 10 on the floor. Layered protection helps on an old machine, and we still run it there, but it compensates for a hole rather than closing it.

Option 1: Upgrade the PC you already have

If the machine passes the check, this is the cheapest path by a wide margin. The upgrade is free on eligible hardware and keeps files and applications in place. Budget about an hour per machine, most of it waiting, plus a short adjustment for whoever uses it: the Start menu moved, and that’s roughly the extent of the drama.

Back up first, and upgrade two machines before you touch twenty. The classic failure is doing them all on one afternoon and finding the single thing that won’t come along, usually an older specialty application or a scanner with an ancient driver.

Option 2: Replace the machine

If it fails the check, this is usually the answer, and the resistance to it doesn’t survive arithmetic. A PC without TPM 2.0 or Secure Boot is old enough that its battery, drive, and fan are already on their own countdown. The choice isn’t spend or don’t spend. It’s whether to spend on a machine with years of support ahead of it, or on deferring that decision for one with none.

Effort: budget, procurement, and a couple of hours per person to move files and sign back into accounts. Spread over a quarter that’s routine. Compressed into the second week of October it isn’t. If you’ve never priced a day of everyone-stopped, our downtime cost calculator does it in a minute, and it tends to reframe what a new laptop is worth. Confirm the data is backed up and restorable before any machine leaves the building.

Option 3: Buy Extended Security Updates as a bridge

Microsoft will sell you more time. Be clear on what you’re buying: security patches only, no new features, no technical support beyond the updates themselves.

For businesses, ESU is sold through volume licensing at $61 per device for year one, and the price doubles every consecutive year, to a maximum of three. It’s cumulative: skip year one and buy in year two, and you pay for both.

You may have heard about the cheap version, a one-time $30 payment or free by syncing your PC settings. That’s the consumer program, and Microsoft’s consumer ESU page says plainly it can’t be used in commercial scenarios, with no enrollment offered on devices joined to a company domain or under central device management.

So ESU is for narrow cases: equipment that genuinely can’t move yet, a lease ending in spring, a budget that lands next fiscal year. It’s a bridge to a specific date, not a plan.

Option 4: Move the work instead of the machine

Sometimes the better question isn’t which Windows the PC runs, but whether the work needs to live on that PC at all.

If your files already sit in Microsoft 365 or Google Workspace and your main business application opens in a browser tab, the hardware underneath matters far less than it used to. That opens options the other three don’t: a cloud desktop that delivers Windows 11 to whatever device someone already has, or retiring a tower that only existed to run one program that now runs online. More thought up front, and it shrinks the next refresh too. It’s where our cloud and infrastructure conversations usually start.

Does Office stop working too?

Not on October 14. Microsoft has committed to security updates for Microsoft 365 Apps on Windows 10 for three years past the operating system’s end of support, through October 10, 2028. Read the rest of that page before you relax: if a problem appears only on Windows 10, Microsoft says support will ask you to move to Windows 11 first. A patched Office on an unpatched operating system is a good lock on a door in an unlocked house.

How we’d spend the next four weeks

1. Inventory. Every Windows PC, its version, and whether it passes the Windows 11 check. Nothing else matters until this list exists.
2. Sort it into three piles: upgrade now, replace, genuinely stuck.
3. Start the easy pile, two machines first, and get quotes moving for the replacements.
4. Deal with the stuck pile. That’s where ESU, a cloud desktop, or fencing a machine onto its own bit of network earns its keep.

The inventory is a Saturday morning if you’re patient. What’s worth handing off is the stuck pile and the sequencing: the old application nobody can reinstall, the equipment with a vendor-locked driver, moving thirty people without losing a day of billing. That’s what we take on under managed IT, and it’s much calmer in September than in November.

If you’d like a second opinion on your list, we offer a free assessment: what you’ve got, what can upgrade, what should be replaced, and roughly what that costs. Or email hello@cohesivesecurity.com. We work on-site with businesses across Rock Hill, SC and the Charlotte metro, and support clients remotely well beyond it.