Windows 10 ESU Year 2 began on October 14, 2026, and the per-device price doubled from $61 to $122, according to Microsoft’s official Extended Security Updates documentation. If your business skipped Year 1, Microsoft’s rules mean you now have to pay for both years at once to get covered. For most Boston-area small businesses still running Windows 10 machines, the real question isn’t whether to swallow the doubled fee, but whether that money is better spent finishing the move to Windows 11.
- Business ESU Year 2 costs $122 per device, double the $61 charged in Year 1.
- ESU purchases are cumulative: skip Year 1, and you pay for Year 1 and Year 2 together before any device is covered.
- Commercial coverage caps at three years total, so the program ends for businesses in 2028 no matter when you enroll.
- Personal Windows 10 PCs have a separate program, now extended through October 12, 2027, that does not cover domain-joined or company-managed devices.
- For hardware already four or five years old, replacing it can cost less over three years than paying escalating ESU fees on a machine you’ll have to retire anyway.
What actually changed on October 14, 2026?
Windows 10 reached its end-of-support date back on October 14, 2025. Businesses that wanted continued security patches could enroll in the paid Extended Security Updates program starting then, at $61 per device for the first year. One year later to the day, that first year closed out and Year 2 began, automatically moving the per-device price to $122. Microsoft built it this way on purpose: ESU is meant to be a costly, temporary bridge rather than a long-term substitute for upgrading, with pricing that climbs each year so staying on Windows 10 keeps getting less attractive.
How much is this going to cost a small office?
A 15-PC business enrolling for the first time now owes $61 plus $122 per device, or $2,745 total, just to get current through Year 2. A business that enrolled on time last year already paid $915 for Year 1 and owes another $1,830 for Year 2, landing at the same $2,745. By the time Year 3 arrives in October 2027 at roughly $244 per device, that same office is looking at close to $6,500 cumulative just to keep aging hardware patched through the end of the program.
Does the free consumer extension help my business at all?
Probably not directly. Microsoft’s consumer ESU program now runs through October 12, 2027, available free by syncing Windows settings, free by redeeming 1,000 Microsoft Rewards points, or for a one-time $30 fee. That’s a real option for a sole proprietor on a personal laptop, or an employee’s home PC that occasionally touches business email. But it does not apply to domain-joined machines or anything enrolled through volume licensing, which is how most Boston businesses with more than a handful of PCs are set up. Mixing up the two programs is an easy way to assume you’re covered when you aren’t.
Should you pay for ESU or just replace the PC?
This is really a hardware-age question. If a machine is two or three years old and simply hasn’t been upgraded to Windows 11 for compatibility or licensing reasons, paying for ESU while you sort that out can make sense. If a machine is already four, five, or six years old, the math tips the other way fast: a new business-class PC capable of running Windows 11 comfortably often costs less than three years of stacked ESU fees, and you get a faster, warrantied machine instead of a ticking clock. We covered the broader end-of-support timeline in our Windows 10 end-of-support and ESU explainer, and our piece on budgeting for small business IT walks through spreading hardware refreshes over a year instead of absorbing them all at once.
What should you do this week?
Pull a list of every PC still running Windows 10 in your office, note its age, and check whether it’s enrolled in ESU or has been quietly running unpatched since last October. Devices with no ESU coverage have gone over a year without critical patches, a real exposure if they touch email, client data, or financial systems. Sort machines into “keep patching for now” and “replace before Year 3 pricing hits” rather than treating the whole fleet the same way.
Frequently asked questions
How much does Windows 10 ESU Year 2 cost per device? Year 2 costs $122 per device for commercial customers, double the $61 Year 1 price, per Microsoft’s official documentation. The price doubles again for Year 3.
Can my business skip Year 1 and just buy Year 2? No. ESU is cumulative, so skipping Year 1 means paying for Year 1 and Year 2 together before your devices are covered.
Does the free consumer Windows 10 ESU extension apply to my business PCs? No. The free and low-cost consumer options, running through October 12, 2027, cover personal PCs only, not domain-joined or commercially managed business devices.
Is it cheaper to pay for ESU or replace the PC? It depends on age. For a PC already four or five years old, replacement often costs less over three years than stacking ESU fees on a machine you’ll eventually retire anyway.
Running an unplanned ESU bill is a sign the Windows 11 transition got stuck somewhere, whether that’s a few holdout PCs, a licensing question, or just not knowing which machines are actually covered right now. Boston Managed IT offers a free 15-minute Microsoft 365 or security review to sort out exactly which of your PCs need ESU, which should be replaced, and what that’s going to cost over the next year. Call (617) 322-5155 or set up a time at bostonmit.com/contact.
— Boston Managed IT
