Windows 10 extended security updates and end-user computing decisions

Windows 10 Security Updates Just Got Twice as Expensive. Make It a Leadership Decision, Not a Help-Desk Ticket.

Windows 10's first year of extended security updates ended October 13. Here's how mid-sized companies can weigh paying for Year 2, refreshing PCs at higher prices, or modernizing desktops, and budget for 2027.

By Donald D. Hook — Former CTO & CIO | Founder, Full On Consulting | Central Florida

Published October 26, 2026

On October 13, a deadline passed that many leadership teams didn't notice. The first year of Microsoft's Extended Security Updates (ESU) for Windows 10 ended. The same day, Microsoft released a record 1,411 security fixes, including one already being exploited. Any Windows 10 PC that isn't enrolled in Year 2 didn't get them.

Most companies hand this to the help desk: count the machines, buy the licenses, move on. I think that's a mistake. Between the ESU price doubling, PC prices going up and the security exposure, this has become a capital and risk decision that belongs in front of the CEO and CFO, right in the middle of 2027 budgeting.

What Changed on October 13

•ESU Year 2 costs $122 per device, double Year 1, and covers you through October 12, 2027. Year 3 doubles again to $244 and is the last year offered.
•Joining late costs extra. Coverage is cumulative, so if you skipped Year 1 you pay for it too before Year 2 applies. Until you enroll, those machines aren't getting security patches.
•Many companies are still exposed. Lansweeper puts roughly one in six enterprise Windows PCs on Windows 10. Healthcare, retail and manufacturing have the highest shares.
•The risk gap is real. The average Windows 10 device carries nearly three times as many known vulnerabilities as a Windows 11 device.

Why "Just Buy New PCs" Got Harder

•PCs cost more. IDC expects average PC prices to rise about 18% in 2026, as AI data centers soak up memory supply. It doesn't expect meaningful relief before late 2027.
•Supply is tighter. Worldwide PC shipments fell about 20% last quarter. Large orders may take longer to fill.
•Most machines don't need replacing. Only a small share of enterprise Windows 10 devices actually fail Windows 11's hardware requirements. Many companies are paying to extend support on PCs that could be upgraded for free.

The Three Real Options

Every Windows 10 device you have falls into one of three groups:

•Upgrade in place. The hardware qualifies for Windows 11. This is usually a planning and testing problem, not a money problem. The work is application compatibility, user communication and scheduling.
•Extend and contain. It runs a line-of-business application or specialty equipment that can't move yet. Pay for ESU Year 2, segment it off the network and set a hard retirement date.
•Replace or virtualize. The hardware is old or doesn't qualify. Before you buy a like-for-like laptop, ask whether some roles would be better served by virtual or cloud desktops (Citrix, Azure Virtual Desktop or Windows 365). Call center staff, seasonal staff and contractors often are.

When I led an end-user computing and infrastructure transformation for 18,000 employees, the biggest savings didn't come from negotiating hardware prices. They came from matching each group of users to the right kind of device, instead of giving everyone the same laptop.

Where Companies Get This Wrong

•They treat ESU as a renewal and pay for another year with no exit plan.
•They don't have an accurate inventory, so they over-buy licenses or miss machines.
•They push the decision into 2027 and then buy hardware at peak prices on short notice.
•They forget about the cyber insurance questionnaire, which increasingly asks about unsupported operating systems.

What to Do Next

☐Pull a current inventory: every Windows 10 device, its age, its owner and whether it qualifies for Windows 11.
☐Confirm whether you're enrolled in ESU. If not, assume those devices are unpatched today.
☐Sort each device into upgrade, extend-and-contain or replace/virtualize.
☐Get updated hardware quotes now, and build a 2027 budget line with a contingency for price increases.
☐Check your key applications for Windows 11 compatibility before you schedule upgrades.
☐Set a retirement date for the last Windows 10 device and give someone ownership of it.

If you're still building next year's plan, my earlier piece on 2027 IT budgets built on prices that no longer exist covers the wider cost picture.

Frequently Asked Questions

How much does Windows 10 Extended Security Updates cost for businesses?

For commercial customers, ESU cost $61 per device in Year 1, which ended October 13, 2026. Year 2 costs $122 per device and runs through October 12, 2027. Year 3, the last year offered, costs $244 per device through October 10, 2028.

Can we still buy Windows 10 ESU if we skipped Year 1?

Yes, but coverage is cumulative. A company that enrolls late also pays for Year 1 before Year 2 applies. Until those devices are enrolled, they are not receiving security patches.

Should we pay for ESU, upgrade to Windows 11 or replace our PCs?

Sort every device into three groups. Upgrade machines that qualify for Windows 11, which is free. Pay for ESU only on machines tied to applications that cannot move yet, and isolate them with a hard retirement date. Replace old or ineligible hardware, and consider virtual or cloud desktops for roles that do not need a full laptop.

Let's Turn a Deadline into a Plan

At Full On Consulting, we help mid-sized companies and nonprofits across Central Florida, from Orlando to Leesburg and The Villages, modernize their desktops and infrastructure without overspending. We bring an independent view: we don't resell hardware or licenses. Our recommendation is about what fits your people, your applications and your budget. Learn more about our infrastructure modernization services.

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