Windows 10 stopped receiving security updates on October 14, 2025. If you are reading this on a Windows 10 machine, it still turns on, still runs your practice management software, and still feels fine. That is exactly the problem. Nothing breaks on the day support ends — the risk just accumulates quietly.
Plenty of Western New York businesses bought themselves a year with Microsoft’s Extended Security Updates program. That year is almost up. In October 2026 the price doubles, and the math gets meaningfully worse for anyone who has been waiting to decide. Here is what is actually changing, and what we would tell you to do about it.
What actually happened in October 2025
As of October 14, 2025, Microsoft no longer provides Windows 10 with quality updates, feature updates, or technical support. Security and reliability fixes stopped. The machines kept working, which is why this has been such an easy problem to postpone.
Microsoft’s paid escape hatch is the Extended Security Updates (ESU) program. It buys you critical and important security patches — nothing else — for up to three years past end of support. For businesses, Year One was priced at $61 per device through volume licensing. There is no minimum order; you can buy a single license if you only have one holdout machine.
The October 2026 deadline that matters now
Two details in the ESU program’s fine print are the reason we are writing about this in July rather than September.
The price doubles every year
Year One was $61 per device. Year Two is double that. Year Three doubles again. A twenty-machine office that shrugs and renews for another year is not paying $1,220 — it is paying roughly $2,440, and about $4,880 the year after that. ESU is deliberately priced to be a bridge, not a plan. Microsoft wants it to hurt a little more each year, and it does.
ESU is cumulative — you cannot skip a year
This is the one that catches people. You cannot decide in late 2026 to just buy Year Two coverage. Microsoft’s licensing terms are explicit that ESU purchases are cumulative: if you enroll in Year Two, you must buy Year One as well. Skipping the first year to save money does not save money. It defers the same bill and adds the doubled rate on top of it.
You also cannot buy a partial period. ESU is sold by the year — there is no six-month option to get you to a spring hardware refresh.
What ESU does not get you
It is worth being blunt about how thin this coverage is, because “we’re on ESU” sometimes gets treated as though the problem is solved.
- No technical support. ESU covers activation and installation of the updates themselves. If Windows 10 breaks in some other way, you are on your own.
- No non-security fixes. Bugs that are not security bugs do not get patched. Neither do reliability issues.
- No new features, ever. The gap between your machines and everyone else’s widens every quarter.
- Only critical and important patches. Vulnerabilities rated below that threshold simply stay open.
- Your device has to be on version 22H2. Older Windows 10 builds are not eligible at all. If you have a machine that has not taken an update in two years, check this first.
There is one bright spot: Windows 10 virtual machines running in Windows 365, Azure Virtual Desktop, and Azure VMs get ESU at no extra cost. If part of your environment is already virtualized, that portion may not need a line item at all.
If you handle patient or card data, this is a compliance question too
For the dental and medical practices we support, the Windows 10 question is not purely a budget question.
Running an unsupported operating system is not automatically a HIPAA violation. What it is, unambiguously, is a finding your risk analysis has to account for. The Security Rule expects you to identify risks to electronic protected health information and actually manage them. An unpatched workstation sitting on the same network as your practice management system is a risk you now know about — and documented awareness without a remediation plan is a worse position than not having looked.
If you take card payments, PCI DSS points the same direction. The current version of the standard expects you to review your hardware and software for end-of-life status on a regular schedule and to have a documented plan for anything that has aged out. “We are still on Windows 10 and figuring it out” is not that plan. “We are on ESU through October, with fourteen machines replaced by Q4” is.
What to do in the next 90 days
You have roughly a quarter before Year Two pricing takes effect. That is enough time to do this properly instead of in a panic.
- Get an actual count. Not an estimate. How many Windows 10 devices are on your network, which build are they running, and what does each one do? The forgotten machine driving an X-ray sensor or a label printer is the one that will derail the project.
- Sort them into three piles. Upgradeable to Windows 11 in place; needs replacement hardware; stuck on Windows 10 because a vendor application requires it.
- Call the vendors in pile three. Practice management, imaging, and point-of-sale vendors have had years to certify Windows 11. Many have. Some quietly did it last year and never told their customers.
- Price replacement against ESU honestly. A business-class desktop amortized over four years often costs less per year than two years of escalating ESU on a machine that is already five years old — and you get the performance back, too.
- Isolate whatever truly cannot move. If a device has to stay on Windows 10, it should be segmented, restricted from general internet access, and documented as an accepted risk with compensating controls.
The honest recommendation
For most offices we work with in Buffalo, ESU made sense for Year One. It was cheap, it bought time, and it let hardware replacement happen on a normal budget cycle instead of an emergency one.
Year Two is a different calculation. At double the price, for security patches only, on hardware that is another year older, ESU stops being a bridge and starts being rent. The businesses that come out of this well are the ones that use the remaining months to finish the migration — not the ones that renew again and have this same conversation in 2027 at four times the price.
If you are not sure what is still running Windows 10 on your network, that is the place to start, and it is not a large project. We can inventory it, tell you which machines can upgrade in place, and give you a real number for the ones that cannot. Get in touch and we will take a look before the October pricing change, not after it.