From our archive: Originally published May 26, 2026. Product features, pricing and availability mentioned in this article may have changed.

Key Takeaways

Windows 10 officially lost standard support in October 2025. Extended Security Updates (ESU) fill the gap, and the first ESU year ends in October 2026.
Businesses can pay for more ESU years at a higher price each year. Without ESU, Windows 10 gets no security patches, and any vulnerabilities discovered stay open permanently.
Millions of PCs are still running Windows 10. Many businesses are treating ESU as a long-term solution rather than a short runway to plan a proper upgrade.
Some older machines won’t meet Windows 11’s hardware requirements. You need to know which ones now, not in September.
Businesses that delay planning face rushed hardware purchases, staff disruption, and potential issues with cyber insurance and compliance requirements.

If You Still Rely on Windows 10 Extended Support, Here’s What Happens Next

Quick answer: The first year of Windows 10 Extended Security Updates (ESU) ends in October 2026. Businesses can pay for more years, at a higher price each year, but without ESU, Windows 10 gets no security patches and any vulnerabilities found stay unpatched. Businesses running Windows 10 without coverage face real security exposure, potential compliance issues, and problems with cyber insurance coverage.

Windows 10 end-of-support illustration with an hourglass

A lot of business owners hear “Windows 10 Extended Security Updates” and think the problem is handled. The deadline passed, they signed up for ESU, and the machine still boots up fine every morning. So what’s the rush?

Here’s the thing: ESU was never meant to be a permanent fix. It’s a short runway. And the cheapest part of that runway ends in October 2026.

If you’re in that camp right now, this post is worth five minutes of your time. Because the decisions you make (or put off) between now and then will have a real impact on your business.

What ESU Actually Means

Windows 10 reached end of standard support in October 2025. That’s not the end of the world on its own, but it does mean Microsoft stopped adding new features and stopped releasing routine updates for the OS.

Extended Security Updates fill part of that gap. If you signed up, your machines still receive critical security patches. Things still work. You can reasonably argue you’re covered for now.

But “for now” comes with a price tag. The first ESU year runs to October 2026, and each additional year for businesses costs more than the last.

Important: ESU is not a long-term strategy. Microsoft designed it to give businesses time to plan a proper migration, not to extend Windows 10 indefinitely, and it ends for good after its final year.

Once ESU coverage ends, Windows 10 is completely unsupported. No patches. No fixes. No responses to newly discovered vulnerabilities. Whatever security gaps exist at that moment stay open permanently.

Why Unpatched Windows 10 Machines Become Targets

Here’s why this matters more than a typical software update: attackers actively scan for machines running outdated, unpatched operating systems.

Once Microsoft announces that Windows 10 is fully end-of-life, researchers and bad actors alike will begin probing for vulnerabilities. And there will be no patches coming. Every flaw discovered after that becomes a permanent opening on any machine still running Windows 10 without ESU.

Worth knowing: As of early 2026, millions of PCs worldwide are still running Windows 10. Even with a well-publicized deadline, a large portion of those machines remain unupgraded. That’s a significant attack surface that will only grow more attractive to cybercriminals after support ends.

It’s easy to look at that situation and assume it won’t affect your business specifically. But it doesn’t take a targeted attack to cause real damage. Automated scanning tools don’t pick their targets. They find what’s exposed and exploit it.

Additionally, many of those vulnerabilities will be publicly documented in security databases. Attackers don’t need advanced skills when the roadmap is public.

It’s More Than a Tech Problem

Running an unsupported OS isn’t just a security concern. It starts to affect other parts of how you do business.

Cyber insurance policies increasingly require that covered systems run supported, patched software. If you file a claim and the insurer finds your systems were running an end-of-life OS at the time of the incident, you may find yourself without coverage when you need it most.

Heads up: Some cyber insurance applications now ask directly whether your endpoints run supported operating systems. Answering incorrectly, or simply not knowing, can void a claim or affect your ability to renew coverage.

Beyond insurance, supplier and client requirements are shifting too. Some industries and larger business partners expect vendors to meet minimum security standards. Running an unsupported OS could put you offside with those expectations, even if no formal audit ever takes place.

So the risk here is commercial as well as technical. That changes the urgency of the conversation.

Some of Your PCs Won’t Make the Jump

This is where timing really matters. Windows 11 has stricter hardware requirements than Windows 10. Specifically, it requires a TPM 2.0 chip and a processor from a supported generation. A lot of older machines simply don’t qualify.

That means the path forward isn’t as simple as pushing an upgrade. You need to know, for each machine in your business, whether it can run Windows 11 or whether it needs to be replaced.

Two paths forward:

Upgrade: If the PC meets Windows 11 hardware requirements, you can migrate it. Some machines may need a configuration check or driver updates first.
Replace: If the PC doesn’t qualify, you’re looking at new hardware. That’s a purchasing decision, a procurement timeline, and a setup and migration process, all of which take time.

Finding out in August that half your machines can’t run Windows 11 is a bad situation. Finding out now gives you options, a real budget conversation, and a sensible timeline.

Furthermore, staggering hardware replacements across several months is much easier on your budget than a panic-buy scramble in September.

What to Do Before the Deadline Hits

The good news is that October 2026 is still a few months away. There’s enough time to handle this properly if you start now. Here’s a straightforward approach.

Windows 10 Exit Plan: Steps to Take Now

Audit your devices. List every PC and laptop in your business and identify which OS it’s running. If you don’t have that list already, that’s the first problem to fix.
Check Windows 11 compatibility. Microsoft’s PC Health Check tool will tell you quickly whether a machine qualifies for Windows 11. Run it across your fleet.
Separate upgrades from replacements. Group your machines into “can upgrade” and “needs replacing.” This gives you a clear picture of your actual cost and timeline.
Plan replacements first. New hardware takes time to procure, configure, and migrate. Start there. Upgrades are faster and can follow.
Set a deadline of your own. Don’t aim to finish in October. Aim for July or August. That gives you a buffer if anything goes sideways.
Review your cyber insurance policy. Check what your insurer requires around supported software. If you’re not sure, ask your IT provider.

The businesses that handle this well aren’t the ones with the biggest IT budgets. They’re the ones that started planning early and gave themselves room to do it right.

And if you’d rather not manage this audit yourself, that’s exactly what a managed IT partner is for.

Don’t Wait Until September to Figure This Out

If your business is still running Windows 10, now’s the right time to find out where you stand. We’ll check your devices, tell you which ones qualify for Windows 11, and help you build a plan that fits your budget and timeline.

Call us: 330-353-8420
Email: info@cybershift.com
Schedule online: cybershifttech.com/contact

No pressure. No jargon. Just a straight conversation about where you stand and what, if anything, needs to change.

About the Author
John Wheeler is a managed IT and Microsoft 365 specialist at Cyber Shift, a trusted IT provider serving small businesses across Northeast Ohio, including Canton, Akron, and Cleveland. He helps local teams get more from the tools they already use, with a focus on practical configuration and day-to-day productivity.

Frequently Asked Questions

What happens when Windows 10 Extended Security Updates end?

When a machine’s ESU coverage ends, Microsoft stops releasing security patches for it. Any vulnerabilities discovered after that will remain unpatched. Machines still running Windows 10 at that point become progressively easier targets for attackers over time.

Can I just keep using Windows 10 after October 2026?

Technically, yes. The machine won’t stop working. But unless you pay for another ESU year, you’ll be running an OS with no security updates, which creates real exposure. You may also run into problems with cyber insurance coverage, compliance requirements, or software compatibility as vendors drop support for the platform.

How do I know if my PC can run Windows 11?

Microsoft’s free PC Health Check tool gives you a quick answer. The main requirements are a compatible processor (generally 8th-gen Intel or newer, or AMD Ryzen 2000 and up) and a TPM 2.0 chip. Many machines bought before 2018 won’t qualify. An IT audit will confirm your full fleet’s status.

Is Windows 11 that different from Windows 10?

The day-to-day experience is similar. The Start menu and taskbar look a little different, but most of your apps and workflows carry over without issue. Most users adapt within a few days. The bigger concern is usually hardware compatibility and application testing, not the interface itself.

What if we just bought our Windows 10 machines a couple of years ago?

Hardware age doesn’t automatically mean Windows 11 incompatibility, but it doesn’t guarantee compatibility either. A machine bought in 2020 or 2021 might qualify, or it might not, depending on the processor and TPM configuration. The only way to know for certain is to run the compatibility check on each device.

How can Cyber Shift Technologies help with this?

We can audit your devices, identify which ones qualify for Windows 11, and flag which ones need replacing. From there, we’ll help you build a realistic migration plan with a timeline that works for your business. We serve small and mid-sized businesses across Canton, Akron, Cleveland, and the broader Northeast Ohio area. Call us at 330-353-8420 or visit cybershifttech.com/contact to get started.

Windows 10 End of Support: Plan Now