Windows 10 Extended Security Updates cost $61 per device for Year One, and the price doubles every year after that: $122 for Year Two, $244 for Year Three, for a maximum three-year total of $427 per device. The license is also cumulative, which means waiting to enroll doesn’t save money. It just adds the bill you skipped onto the one you owe now.
Here’s the decision a real, sizable share of firms are quietly putting off, not a stray handful. Windows 10 reached its official end of support on October 14, 2025. The computers didn’t stop working that day, and that’s exactly the problem. Everything still boots up, email still opens, the practice management software still runs, so it’s easy to assume the deadline was more of a formality than a real one. Meanwhile, the actual clock that matters, the one on Year One ESU pricing, runs out October 13, 2026. After that, staying on Windows 10 gets meaningfully more expensive, one year at a time, by design.
Picture two versions of this decision. In one, a firm already knows it has roughly 50 workstations still on Windows 10, a mix of eligible and ineligible hardware, and gets the whole fleet reviewed and moved before it becomes an emergency. That’s the version of this story that goes well. The other version, the one that plays out far more often, is a business that’s been meaning to deal with this since last October, has maybe enrolled in Year One ESU as a stopgap, and hasn’t actually decided what happens next.
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What Windows 10 ESU Actually Costs, Year by Year?
The Three-Year Pricing Structure
The pricing structure of the Windows 10 ESU program is simple and intentionally uncomfortable. According to Microsoft’s own Extended Security Updates documentation, commercial ESU is billed annually per device: $61 for Year One, $122 for Year Two, $244 for Year Three. If a device stays on Windows 10 ESU for the full three years permitted, the total cost is $427 per device, on top of whatever that device would have cost to simply replace or upgrade to Windows 11 in the first place.
The Cumulative Enrollment Trap
The detail that catches people off guard is the cumulative rule. ESU licensing doesn’t let you join partway through at the current year’s rate. If your firm skips Year One and decides in the second year that it’s time to enroll, you owe both years, $61 plus $122, before that device is even covered going forward. There’s no discount for waiting, and no way to buy just the year you’re currently in. The only thing waiting actually accomplishes is a bigger bill whenever you do decide to act.
Eligibility and One Notable Exception
There’s also an eligibility requirement worth knowing before you assume ESU is even an option: devices need to be running Windows 10 version 22H2 to qualify. If any of your machines are on an older build, that’s worth checking now, since it affects whether ESU is available to you at all, not just what it costs.
One narrow exception worth knowing: ESU is included at no additional cost for Windows 10 virtual machines running in Windows 365 or Azure Virtual Desktop. If your firm already runs virtual desktops through one of those services, this entire cost conversation may not apply to those specific machines.
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Why This Isn’t Really a “Wait and See” Decision
What ESU Actually Buys You
It’s worth being direct about what ESU actually buys you, because it’s less than the name suggests. Extended Security Updates covers exactly that: critical and important security updates, and nothing else. No new features, no general technical support beyond that narrow security scope, no fix for the everyday friction of running an aging operating system. You’re paying, at an increasing rate every year, purely to keep critical security updates flowing to hardware and software that Microsoft has otherwise moved on from.
Why the Price Escalates by Design
The escalating price isn’t an accident or an oversight. It’s a deliberate structure meant to make delay progressively less attractive, and it’s working exactly as designed. A firm that treats Year One ESU as a permanent plan rather than a temporary bridge is signing up for a bill that doubles every single year, with no ceiling other than the three-year cutoff itself. After Year Three, ESU isn’t offered again at any price. At that point, an unpatched Windows 10 device is simply unpatched, permanently, for whatever vulnerabilities get discovered from then on.
The Cyber Insurance Angle
There’s a cost to this decision beyond the ESU subscription itself, too. Cyber insurance carriers have started asking specifically about unsupported operating systems during renewal, and some now exclude coverage for incidents traced back to a device running past its end of support date without ESU in place. A firm that’s quietly extended support through ESU without documenting it, or that’s simply kept using Windows 10 with no coverage at all, may find that question harder to answer honestly than expected. That’s worth checking with your broker before your next renewal, not after an incident.
Consumer ESU vs. Business ESU
It’s also worth clearing up a common point of confusion. Windows 10 Home users have access to a separate, much simpler consumer ESU program, sometimes free through a Windows Backup enrollment, sometimes a flat low-cost fee for a single year. That consumer program is not the same thing as the commercial ESU program built for businesses, and it doesn’t extend to Year Two or Year Three the way the business version does.
What a Real Migration Actually Looks Like?
Done well, this isn’t an all-or-nothing switch flipped overnight. A firm with roughly 50 devices, reviewed one by one rather than as a single fleet-wide assumption, is the right approach. Some machines have the hardware to move straight to Windows 11 with a clean upgrade. Some devices require replacement, while others need software compatibility testing before upgrading to Windows 11 safely and avoiding application failures.
The rollout itself works best staggered rather than done all at once, which is what keeps disruption minimal. A cluster of machines moves, the team confirms everything still works the way people need it to, and then the next cluster moves. Nobody comes in on a Monday to find their whole department down at the same time.
That’s the version of this that costs a known, bounded amount of planning time now. Repeatedly renewing ESU without planning wastes money and delays inevitable upgrades, leaving unsupported devices increasingly expensive to maintain long-term unnecessarily.
One more piece worth building into any migration plan, not just this one: confirm your backups are actually current and restorable before any device gets touched, not after. A Windows 11 migration lets you verify your backup strategy before unexpected migration failures expose untested recovery gaps and risks.
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What to Actually Do Before October 2026?
You don’t need to solve this for every device today. You need an honest answer to a few specific questions, per machine, not per fleet.
Which of Our Devices Are Actually Still on Windows 10?
A full inventory is the starting point, and it’s often smaller or larger than owners expect once someone actually checks rather than assumes.
Which of Those Devices Can Upgrade to Windows 11 Cleanly?
Hardware requirements matter here, and not every three or four-year-old machine will qualify. Better to know that now than after Year One ESU has already been paid for a machine that needed replacing anyway.
Which Ones Are Worth Replacing Instead of Upgrading?
Sometimes the honest answer is that a device is old enough that upgrading it is a worse financial decision than retiring it.
Is ESU a Deliberate Bridge, or an Accidental Long-Term Plan?
There’s a real difference between paying $61 once while a specific replacement is already scheduled, and quietly renewing into Year Two and Year Three without ever making an actual decision.
A technology assessment identifies each device’s readiness before October 2026 transforms planning challenges into costly business disruptions and expenses.
If you’d rather have a straight answer about where your fleet actually stands, book a Free Technology Assessment with Right Hand Technology Group and get a real device-by-device plan instead of an annual ESU bill that keeps quietly doubling.
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Frequently Asked Questions
How much does Windows 10 ESU actually cost?
Windows 10 ESU costs $61 in Year 1, $122 in Year 2, and $244 in Year 3 per device.
Can I still use Windows 10 after 2026?
Yes. Windows 10 still works after 2026, but without ESU, it stops receiving security updates and becomes increasingly vulnerable.
Is it worth getting ESU, or should I upgrade to Windows 11?
Choose ESU for temporary protection, but upgrade to Windows 11 for better security, support, and long-term savings.
Can I still upgrade to Windows 11 for free?
Yes. Eligible Windows 10 PCs can upgrade to Windows 11 for free if they meet Microsoft’s hardware requirements.
How do I enroll in the Windows 10 ESU program?
Purchase ESU through Microsoft Volume Licensing or assign licenses using Microsoft Intune or Windows Autopatch for eligible devices.
