The Windows 10 Bill just Went Up

A year ago, Windows 10 end of support kicked in — Microsoft stopped patching it. If your business skipped the upgrade and just... didn't do anything, you got away with it for twelve months. That grace period is about to get a lot more expensive.

What's changing this month

Here's what actually happened: Microsoft ended free support for Windows 10 back on October 14, 2025. For anyone who wasn't ready to move to Windows 11 yet, they created a bridge — the Extended Security Updates program, or ESU. Pay a fee, keep getting security patches, buy yourself time.

That bridge gets a lot more expensive starting this October. Year one of ESU cost $61 per device. Year two — which starts this month — jumps to roughly $122. Year three, after that, is around $244. And if you're running Windows 10 Home instead of Pro, that option disappears completely; there's no ESU path for you at all.

This pricing curve is not an accident. It's Microsoft's way of saying "we'll let you procrastinate, but we're going to charge you more for it every year until you stop." I'd probably do something similar if I were selling operating systems. But if you're running a business on machines that are quietly becoming more expensive to keep alive, it's worth making a gameplan while you still have options.

Why this actually matters

Here's why this matters beyond the invoice. An unsupported machine doesn't just miss out on new features — nobody's patching the holes in it anymore. Every vulnerability discovered after support ends just sits there, wide open, on that one machine, indefinitely. Attackers know exactly which systems stopped getting patched and go looking for them specifically. And it only takes one of those machines on your network to become the way in for everything else.

There's a second hit a lot of business owners don't see coming: compliance and insurance. If you're carrying cyber insurance — and at this point, you probably should be — insurers are increasingly asking whether your systems are still supported. An office full of end-of-life machines can get flagged in an audit, or worse, get you denied at renewal. I've seen it happen to a company that thought their old machines "still worked fine."

What to do about it

So what do you actually do about it? Three options, roughly in order of how much I'd recommend them:

1. If your hardware's from 2019 or newer, check whether it qualifies for a free upgrade to Windows 11. A lot of machines do and nobody's bothered to check.
2. If it doesn't qualify, this is the year to budget for replacing those machines in phases — not all at once, but on a real schedule, not "eventually."
3. ESU exists as an option, but we didn't set our own clients up with it. Paying more every year — on a curve that doubles annually — to delay a decision you're going to have to make anyway, plus now tracking another renewing subscription per device, didn't feel like solving the problem so much as postponing it with extra paperwork. If you go that route anyway, that's a legitimate call for some situations — just go in knowing it's a rental, not a fix, and the clock runs out entirely in October 2028.

The bottom line

My actual takeaway, and it's not "buy new computers from us": do you know, right now, off the top of your head, how many machines in your office are still running Windows 10? If the honest answer is "I'd have to check," that's the twenty minutes I'd spend this week — before the bill gets bigger and the excuse gets weaker.

If you're a client of Revolution Group, you know that a regular part of our service is keeping you informed on the status of all of your equipment and software, as well as helping you develop your annual IT budget, as a regular feature of being your IT partner.

— Rick