When Microsoft ended free support for Windows 10 in October 2025, a lot of business owners took a wait-and-see approach. The machines still turned on. Word still worked. Nothing exploded. So the upgrade got pushed to "next quarter" and then to "next year."

We get it. Replacing a fleet of workstations is expensive, and if the current ones are doing the job, the pressure to change feels artificial. But we're now a full year past the deadline, and the reasons to move are no longer hypothetical. They're showing up on our tickets and in our clients' insurance renewal letters.

Here's what we're actually seeing.

Cyber insurance is starting to say no

This is the biggest one, and the one most owners don't see coming until renewal time. Carriers have gotten specific about supported operating systems, and "Windows 10 with no extended support subscription" is increasingly showing up as a disqualifier — not a rate increase, an outright decline.

We've had two clients this year get renewal letters that essentially said: replace the Windows 10 endpoints by X date or we won't renew. In both cases the deadline was measured in weeks, not months, and the replacement cost hadn't been budgeted.

If your renewal is coming up in Q4 or Q1, check now whether your carrier has added OS requirements. Ours can help you read the fine print if you're not sure — this ties directly into the Security Assessment work we do.

Extended Security Updates are not a long-term plan

Microsoft does offer paid Extended Security Updates (ESU) for Windows 10, and for some businesses that's a reasonable bridge. But it's a bridge, not a destination. The price roughly doubles in year two and doubles again in year three, and there's a hard end date after which no amount of money buys you patches.

We've helped a few clients use ESU strategically — usually when they have a specific line-of-business application that isn't Windows 11 compatible yet and they're waiting on the vendor. That's a legitimate use case. Using ESU as a way to avoid ever thinking about the problem is not.

Third-party software is starting to drop support too

This is the quieter problem. When an OS goes end-of-life, the vendors of the software running on it eventually follow. We're seeing accounting packages, industry-specific tools, and even some browsers starting to say "Windows 11 or newer only" in their release notes.

When that happens, you're not just missing security patches — you're stuck on old versions of the applications your business runs on. Old versions have their own security issues, and they don't get bug fixes for the annoying stuff either.

The hardware question is real, but not as bad as you think

Windows 11 has stricter hardware requirements than Windows 10, most notably around TPM 2.0 and specific CPU generations. A lot of the resistance to upgrading comes from owners assuming they need to replace every machine.

In our experience, it's a mix:

Machines from roughly 2018 onward usually meet the requirements and just need the upgrade run
Machines from 2016-2017 are a coin flip depending on exact model
Anything older than that is almost always due for replacement regardless

The cheapest path is rarely "replace everything." It's usually "upgrade what can be upgraded, replace what has to be replaced, and stage it over one or two quarters instead of all at once." That's the kind of planning we do inside our Managed IT plans — the audit of what you have, what it needs, and what order to do it in.

What about the machines that can't upgrade?

A few honest options:

Replace them. For a lot of front-desk and back-office roles, a decent business-class laptop is under $1,200 and will last 5-6 years. The math often works out better than people expect once you factor in support hours saved.
Repurpose them. An older machine that can't run Windows 11 might still be fine as a dedicated device for one specific task — a print server, a monitoring display, a piece of shop-floor equipment that only runs one program and isn't on the main network.
Segment them. If you have a machine that has to keep running an old OS because of a specific application, we can isolate it on the network so a compromise on that machine can't reach the rest of your business. This isn't a substitute for upgrading, but it buys time safely.

What we'd suggest doing this month

If you haven't looked at this since last October, now is the time — not because something's on fire, but because the runway to do it calmly is shrinking:

Pull an inventory of every machine in your business and its OS version (we can do this in about an hour if you're a managed client)
Cross-reference against Windows 11 compatibility
Get a rough cost for the replacements you'll need
Check your cyber insurance renewal date and its OS requirements
Plan the rollout across Q4 and Q1 so you're not doing it all in one painful weekend

If you're not sure where you stand, we'll do a no-charge inventory and give you a straight answer on what needs to move, what can wait, and what it'll cost. Book a walkthrough and we'll come take a look.

Windows 10 hit end-of-support a year ago. A lot of Cape Breton businesses are still running it.