Windows 10 reached end of life on October 14, 2025. Microsoft stopped releasing security patches for it on that date. If your business is still running Windows 10 machines, those devices are now accumulating unpatched vulnerabilities with every passing month — and that number will only grow.

This isn't theoretical risk. The period immediately after an OS reaches end of life is when attackers specifically target it, because they know patches will never come. We saw this pattern with Windows 7, and it's repeating with Windows 10.

Here's how to plan the migration properly.

Step 1: Know What You're Working With

Before you migrate anything, you need an accurate inventory of every Windows machine in your environment. For each device, you need to know:

The current OS version and build number
The CPU, RAM, and storage specs
Whether the machine has a TPM 2.0 chip

That last point is the one that trips people up. Windows 11 requires a TPM 2.0 (Trusted Platform Module) chip. Most machines manufactured after 2018 have one — but some have it disabled in the BIOS, and some older machines simply don't have it at all.

To check TPM status on a Windows 10 machine, run tpm.msc from the Run dialog. If it shows TPM 2.0 as ready, you're eligible for an in-place upgrade. If it shows no compatible TPM, or TPM 1.2, you have a harder conversation ahead.

The full Windows 11 hardware requirements: 64-bit processor at 1GHz or faster with at least 2 cores, 4GB RAM, 64GB storage, UEFI firmware with Secure Boot, TPM 2.0, and a DirectX 12 compatible GPU. The CPU requirement is the other common blocker — Intel 7th generation (Kaby Lake) and older processors are not supported by Windows 11, regardless of TPM status.

Microsoft's PC Health Check app can scan a machine and give you a pass/fail in about 30 seconds. Run it on every machine before you plan anything.

Step 2: Separate the Hardware That Can't Upgrade

Once you've audited the fleet, you'll have two lists: machines that can run Windows 11, and machines that can't.

For machines that can't upgrade, you have a few options:

Replace the hardware. The most straightforward path. If the machine is more than 5-6 years old, it's probably due for replacement regardless of Windows 11. A business-class Windows 11 Pro machine (Dell OptiPlex, Lenovo ThinkCentre, HP ProDesk) runs $700–1,200 CAD for a reliable unit.
Extended Security Updates (ESU). Microsoft offers paid ESU for Windows 10 — $61 USD per device for the first year. This buys time, not a solution. Factor it in if you have a few legacy machines running specialized software that needs a compatibility window.
Isolate and monitor. If a machine absolutely cannot be replaced or upgraded yet, move it off the main network segment, restrict its internet access, and monitor it closely. This is a risk management decision, not a long-term plan.

Step 3: Choose Your Migration Path

For machines that pass the hardware check, you have two options:

In-place upgrade. You run the Windows 11 installer on the existing Windows 10 machine. Applications, settings, and user data are preserved. This is faster and less disruptive, and it's the right call for most small business environments. The failure rate on in-place upgrades is low when the hardware is healthy — but you should still back up the machine first.

Fresh install (wipe and reload). You wipe the machine and install Windows 11 clean. This takes longer because you need to reinstall applications and restore data, but it results in a cleaner system without legacy cruft. If a machine has been in use for 4+ years and feels sluggish, a fresh install often noticeably improves performance.

Our recommendation: use in-place upgrades for machines less than 3 years old and in good condition. Use fresh installs for older machines or machines with known performance or stability issues.

Step 4: Pilot Before You Roll Out

Don't migrate everyone at once. Pick 2-3 technically comfortable users — ideally people who can handle a hiccup without calling in a panic — and run the first wave of upgrades on their machines. Give it a week.

What you're watching for:

Application compatibility issues (this is rare with mainstream business software, but line-of-business applications sometimes need updates)
Printer driver issues (this is the most common real-world problem)
User confusion with the Windows 11 interface changes

If the pilot goes cleanly, proceed with the rest of the fleet.

Step 5: User Training (Keep It Brief)

Windows 11 looks different enough from Windows 10 that some users will be disoriented. The Start menu is now centered by default (you can move it back to the left in Settings), the taskbar is consolidated, and some right-click menus require an extra click to see all options.

A 15-minute walkthrough covering the key differences is usually enough for most users. Cover: Start menu, search, Settings, Quick Settings panel (the WiFi/battery area), and how to right-click properly. Don't overload people — they'll figure out the rest through use.

Step 6: Leverage Autopilot and Intune for Larger Teams

If you're managing 20 or more machines and your organization is on Microsoft 365 Business Premium, look seriously at Windows Autopilot combined with Intune.

Autopilot lets you configure a new machine by logging into a Microsoft 365 account. The machine downloads its configuration, installs its applications, and joins the domain — all automatically. You don't need to touch it. For fresh installs or new hardware purchases, this eliminates most of the per-machine setup time.

Intune also lets you push Windows 11 upgrade policies to eligible devices across the fleet from a single admin console, without touching each machine individually. Combined with a hardware inventory from your RMM tool, you can manage a fleet migration without being on-site for every device.

Realistic Timeline

| Fleet Size | Timeline | |------------|----------| | 1-10 machines | 1-2 weeks | | 11-30 machines | 2-4 weeks | | 31-100 machines | 4-8 weeks | | 100+ machines | 8-16 weeks (phased by department) |

These assume healthy hardware and no major application compatibility issues. Add buffer for hardware replacement cycles on machines that fail the TPM check, and for any line-of-business software that needs vendor testing before you migrate it.

The sooner you start, the less pressure you're under. Every month you run Windows 10 after end-of-life is a month of unpatched exposure. If you need help running the assessment or managing the rollout, reach out to IPCONNEX — we handle fleet migrations for Montreal businesses regularly.

Windows 11 Migration Guide for Small Businesses