Microsoft doubles the price of Windows 10 security updates on October 14. Here is how to work out, machine by machine, whether paying it makes any sense.
There is a particular kind of technology decision that businesses put off not because it is hard, but because it is unpleasant. Replacing computers that still turn on is one of them.
The machine boots. Someone is using it. It runs the software they need. Nothing is visibly wrong. And every quarter, replacing it gets pushed to the next quarter, where it competes with things that feel more urgent.
Microsoft has now put a price tag on that delay, and the price tag doubles every year. That changes the conversation from a judgment call into arithmetic — which is good news, because arithmetic can be settled.
The short version: Windows 10 stopped receiving security updates on October 14, 2025. You can rent them back from Microsoft for $61 per device the first year, $122 the second, and $244 the third — and the charges are cumulative, so you cannot skip a year and pick up later. Year 2 coverage begins October 14, 2026. Riding it out for all three years costs $427 per machine, and at the end you still own nothing and still have to replace the computer.
First, what actually happened on October 14, 2025
Windows 10 reached end of support. Not “end of mainstream support,” not “reduced support” — end of support. Microsoft stopped shipping security patches for it entirely.
That distinction matters, because a Windows 10 machine today still works exactly as well as it did two years ago. It opens email. It runs the accounting package. Nothing broke. What changed is invisible: every vulnerability discovered in Windows since that date stays open on that machine unless you are paying for Extended Security Updates.
This is worth sitting with for a second, because it is the reason so many businesses are still on Windows 10. There is no alarm. There is no error message. The operating system does not tell you it has stopped being defended. It just quietly becomes a more attractive target every month, as the list of known, unpatched holes gets longer and the tools to exploit them get more automated.
31% of breaches now begin with exploitation of a vulnerability — up from 20% the year before, and the leading entry point ahead of stolen credentials for the first time. Verizon 2026 Data Breach Investigations Report.
An unpatched operating system is not a theoretical risk category. It is the most common one.
What Extended Security Updates actually are
Microsoft’s Extended Security Updates program lets you keep buying security patches for Windows 10 for up to three years past end of support. It is deliberately structured as a bridge, not a destination — and the pricing is designed to make sure you treat it that way.
The pricing, and the trap inside it
Commercial ESU is sold per device, per year, and the price doubles every year:
| ESU year | Coverage window | Price / device |
|---|---|---|
| Year 1 | Oct 15, 2025 – Oct 13, 2026 | $61 |
| Year 2 | Oct 14, 2026 – Oct 12, 2027 | $122 |
| Year 3 | Oct 13, 2027 – Oct 10, 2028 | $244 |
| All three years | through Oct 10, 2028 | $427 |
The trap is that ESU is cumulative. In Microsoft’s own words: “If you decide to purchase the program in Year Two, you have to pay for Year One too, as ESUs are cumulative.” You cannot sit out a year to save money and rejoin later at the current rate. You also cannot buy a partial period — there is no six-month option.
So a business that skipped Year 1 and now wants coverage is not looking at $122 per device. It is looking at $183 — $61 for a year of protection that has already elapsed, plus $122 for the year ahead.
What you are not buying
This is where a lot of businesses have the wrong mental model. ESU is not a support contract. It is narrower than most people assume:
- Critical and Important security updates only. That is the entire product. Anything Microsoft rates below Important does not get fixed.
- No new features. Windows 10 is frozen where it is.
- No non-security bug fixes. If something is broken and it is not a security hole, it stays broken.
- No technical support. Microsoft is explicit: technical support is not included in the ESU program. Their help covers the ESU licensing and installation itself — not Windows.
- Nothing about your applications. Software vendors set their own support lifecycles. Many have already dropped Windows 10 from their supported platform lists, ESU or not. Paying Microsoft does not oblige anyone else to keep supporting you.
One prerequisite that catches people: devices must be running Windows 10 version 22H2 to receive ESU at all. A machine sitting on an older build is not merely unpatched — it is not even eligible for the paid lifeline until it is brought current.
Now run the math on your own fleet
Here is the calculation, and it takes about ten minutes with an accurate device list.
01. Count the machines that are actually still on Windows 10
Not what you think the number is — what it is. In our experience the count is almost always higher than the person answering expects, because of the machines nobody thinks of as computers: the workstation running a scale or a label printer, the PC in the shop that drives a piece of equipment, the reception machine, the laptop in the truck, the one in the back office that only runs one report each month.
02. Price the rental
Multiply. A 25-device example makes the shape of it clear:
| Scenario for 25 Windows 10 devices | Per device | Total |
|---|---|---|
| Already enrolled in Year 1; add Year 2 | $122 | $3,050 |
| Never enrolled; want coverage now (Y1 + Y2) | $183 | $4,575 |
| Ride it all the way out (Y1 + Y2 + Y3) | $427 | $10,675 |
Ten thousand six hundred and seventy-five dollars, to rent an operating system for three years, for twenty-five machines you will still have to replace in 2028. That number tends to end the debate on its own.
03. Price the alternative — honestly
We are not going to quote you a hardware price in a blog post, because it depends on what those machines actually do. A front-desk PC and a CAD workstation are not the same purchase. Use your own recent quotes.
But compare like for like. The real comparison is not “ESU for one year versus a new computer.” It is the full remaining ESU bill for that machine, plus the productivity cost of running aging hardware, plus the risk you are carrying in the meantime, against a machine that stays supported as long as you keep it on a current version of Windows 11 — and that is faster on the day it arrives.
And check the middle option before you assume replacement is the only path. Some Windows 10 machines can simply be upgraded to Windows 11 in place, at no license cost, if the hardware qualifies.
04. Sort every machine into one of three buckets
Bucket 1 · Upgrade in place. The hardware meets Windows 11 requirements: TPM 2.0, UEFI with Secure Boot, an 8th-generation Intel Core processor or newer (or AMD Ryzen 2000 series or newer), at least 4 GB of RAM, and 64 GB of storage. If a machine clears that bar the Windows 11 upgrade itself is free — though eligibility is not the same as adequacy. A 4 GB machine will pass Microsoft’s compatibility check and then frustrate whoever has to use it. For a business fleet, treat the published minimum as the floor, not the target.
Bucket 2 · Replace. The hardware does not qualify, and the machine does ordinary work. This is most of the fleet for most businesses. Sequence the replacements across your budget rather than doing them all in one painful month.
Bucket 3 · Genuinely stuck. This is where ESU earns its price. The machine runs something that cannot move yet.
When paying for ESU is the right answer
We would rather give you the honest version than push everyone toward new hardware. There are real cases where renting another year is the correct business decision:
- A machine controls equipment — a scale, a labeler, a lab instrument, a production line PC — and the vendor has not certified their software on Windows 11 yet. This is common in agriculture, food processing, and manufacturing, and it is not your fault.
- A line-of-business application your company runs on has a Windows 11 version arriving on a known date, and that date is inside the coverage window.
- The device is already scheduled for replacement in a capital cycle that lands a few months out, and you need to bridge the gap.
In every one of those cases, ESU is a bridge with a date written on the far end. What it must never be is a renewal that happens quietly every year because nobody made a decision. That is how you end up paying $427 a machine and still facing the same problem in 2028.
Why this is a September conversation, not a December one
Year 2 coverage begins October 14, 2026 — a few weeks after this post goes up.
If you are enrolled and doing nothing, your bill doubles on that date. If you are not enrolled, that is the date your exposure has been running for a full year, and the catch-up cost has already accrued.
There is also a practical reason not to wait, which has nothing to do with Microsoft. Business-class hardware is ordered, not bought off a shelf. It has to be configured, joined to your network, loaded with your applications, and handed to a person who then needs an hour to find their files. Multiply that by twenty machines and it is a project, not an errand. Projects started in September finish comfortably. Projects started in December finish in February, badly.
While you have the device list open
Two other lifecycle dates are worth checking at the same time, because they hit the same budget:
- Windows Server 2016 reaches end of extended support on January 12, 2027. If you have one, it needs a plan in this budget cycle, not the next one.
- Anything running a Windows 10 build older than 22H2 is not eligible for ESU at all, and needs attention regardless of which bucket it ends up in.
One more thing worth knowing, because it surprises people: if any of your Windows 10 workloads run as virtual machines in Azure, or through Windows 365 Cloud PCs or Azure Virtual Desktop, ESU is included at no additional cost. It is not a reason to move to the cloud on its own — but if a cloud migration was already on your roadmap, this quietly changes the math on it.
The point of all this
Most of the technology decisions we help clients make involve genuine trade-offs, where reasonable people could land in different places. This one mostly does not.
The doubling price is Microsoft telling you, in the clearest language a vendor has available, that this is not a plan. Every year you delay costs twice what the last one did, buys less protection than a supported operating system provides, and ends in exactly the same place: buying the computers anyway.
So run the count. Sort the machines into the three buckets. Price the rental against the replacement with your own numbers. Whatever you decide, decide it deliberately — the expensive outcome here is not choosing wrong, it is not choosing at all.
We will run the count with you.
We inventory every Windows 10 device on your network, tell you which ones can upgrade to Windows 11 for free, which ones need replacing, and which ones genuinely need another year of ESU — with the dollar figures attached. You get a prioritized list you can hand straight to whoever approves your budget.
No internal IT? That is normal here. Many of our clients have none at all — we serve as their complete technology department, from help desk to strategic planning.
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