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Windows 10 Support Is Gone — Here's Why Your Summer Is the Time to Move to Windows 11

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Quick answer

Microsoft ended free support for Windows 10 on October 14, 2025, which means those PCs no longer receive security patches unless you're paying for Extended Security Updates (ESU) — and for consumers that paid lifeline runs out on October 13, 2026. Every month a business keeps running unsupported Windows 10 is a month of newly discovered vulnerabilities that will never be fixed, making the machines an easy target and, in many cases, a compliance and cyber-insurance problem.

The summer slowdown is the ideal window to migrate: fewer active deadlines, staff cycling through vacation, and time to test line-of-business apps before the fall rush. CairiTech, an Aurora, Ontario managed IT and cybersecurity provider, helps Greater Toronto Area businesses — including Architecture, Engineering, and Construction (AEC) firms running Revit and AutoCAD — plan and execute a clean Windows 11 rollout with no surprises.

3 min read posted on 07/12/26

Did Windows 10 really stop getting updates?

Yes — Microsoft officially ended mainstream support for Windows 10 on October 14, 2025, so it no longer ships free security updates, feature updates, or technical support. The operating system still boots and runs, which is exactly what makes it dangerous: it feels normal while quietly becoming less safe every patch cycle. Windows 10 is what security teams call "end of life" — still in use, but no longer defended.

What are Extended Security Updates, and how long do they last?

Extended Security Updates (ESU) are paid, security-only patches Microsoft offers as a temporary bridge for organizations that can't migrate immediately. For consumers, ESU coverage runs from October 15, 2025 through October 13, 2026; for businesses, ESU can be purchased for up to three years, ending October 12, 2027, with the price rising each year. ESU is a stopgap, not a strategy — it buys planning time, nothing more.

Why is running unsupported Windows a real security risk?

Running an unsupported operating system is risky because attackers specifically hunt for unpatched systems, and every vulnerability found after end of life stays open forever. Historically, one of the most damaging examples was WannaCry, which spread through a known Windows flaw and hit an estimated 200,000+ machines across 150 countries — many of them unpatched. When a platform stops receiving fixes, each new flaw becomes a permanent, publicly known doorway.

There's a business angle too: many cyber-insurance policies and compliance frameworks (including ISO 27001 controls) expect supported, patched systems. An unsupported fleet can quietly void coverage or fail an audit.

Windows 10 ESU vs. upgrading to Windows 11 — which makes sense?

For most GTA businesses, upgrading to Windows 11 is the better long-term move, while ESU only makes sense to cover machines that genuinely can't upgrade yet. Here's the trade-off:

Stay on Windows 10 + ESU

Security patches:

Security-only, temporary

Cost trend:

Rises every year

New features:

None

Hardware needs:

Existing PCs

End date:

Oct 2026 (consumer) / Oct 2027 (business)

Upgrade to Windows 11

Security patches:

Full ongoing updates

Cost trend:

One-time migration

New features:

Yes (security + productivity)

Hardware needs:

TPM 2.0, newer CPU required

End date:

Supported for years

Windows 11 also raises the security floor: it requires TPM 2.0 (a hardware security chip) and enables features like virtualization-based security by default, which is why Microsoft is pushing the move rather than extending Windows 10.

What's the smart way to plan a summer migration?

The smart way to migrate is to inventory first, test second, and roll out in waves — not to flip every machine at once. A clean plan looks like this:

Inventory every device and check Windows 11 eligibility (CPU, TPM 2.0, RAM).
Flag replacements — older workstations that can't meet the requirements need budgeting now, not in October.
Test critical apps — verify Revit, AutoCAD, accounting, and industry tools on Windows 11 before wide deployment.
Migrate in waves, starting with a pilot group, so any issue is caught small.
Back up first — always image or back up before an OS change.

Doing this over a quieter summer means the fall arrives with a supported, secure fleet instead of a last-minute scramble.

October will arrive faster than it feels like in July. Moving now — while the calendar has room — turns a looming deadline into a routine project. See our managed IT services and support services for how we handle rollouts end to end. Book your free discovery call with CairiTech today and we'll map your Windows 11 migration before the fall rush.

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Frequently asked questions

Can I still use Windows 10 after October 2025?

Yes, it will keep running, but without free security updates it becomes progressively less safe. You'd need paid ESU to keep receiving security patches while you plan your move to Windows 11.

Is the upgrade to Windows 11 free?

For eligible PCs, the Windows 11 upgrade itself is free through Windows Update. The cost usually comes from hardware — older machines that lack TPM 2.0 or a supported CPU may need replacing.

How do I know if my PC can run Windows 11?

Windows 11 requires TPM 2.0, a supported 64-bit processor, 4 GB+ RAM, and Secure Boot. Microsoft's PC Health Check tool reports eligibility, and an IT partner can inventory a whole fleet at once.

What happens to our cyber-insurance if we stay on Windows 10?

Many policies require supported, patched operating systems, so running unsupported Windows 10 can jeopardize a claim or renewal. Check your policy wording and prioritize migrating any covered systems.

Written by the Cairitech team — Greater Toronto Area managed IT and cybersecurity specialists, serving Ontario businesses (including AEC firms) since 1990. Head office: 1-2 Vata Court, Aurora, ON. Phone: +1 (416) 361-1441.

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