Windows 10 End of Support: What GTA Businesses Must Do Now

Windows 10 reached its end of support on October 14, 2025. If your business still has Windows 10 machines in daily use, they are no longer receiving free security updates from Microsoft — every month that passes, newly discovered vulnerabilities on those PCs stay unpatched. For businesses in Toronto and the GTA still running a fleet of Windows 10 desktops and laptops, this is now an active risk, not a future deadline.

What 'End of Support' Actually Means

The machines do not stop working. What stops is the flow of security patches, bug fixes, and technical support. In practice that means: new vulnerabilities remain exploitable, compliance and cyber-insurance questionnaires that ask 'are all systems supported and patched?' become harder to answer honestly, and software vendors progressively drop Windows 10 from their supported platforms.

The last point catches businesses off guard: over time, the applications you rely on — accounting packages, browsers, line-of-business tools — release versions that will not install or are not supported on Windows 10, so the problem compounds even if you accept the security risk.

Why Cyber Insurance Makes This Urgent

Cyber-insurance applications routinely ask whether you run unsupported (end-of-life) operating systems. Running unsupported Windows 10 without a documented plan can affect coverage or become a problem during a claim. If your business carries or is shopping for cyber insurance, unsupported endpoints are one of the first things to deal with.

Your Three Realistic Options

1. Upgrade Eligible PCs to Windows 11 (Free)

If a PC meets Windows 11's hardware requirements — which include TPM 2.0 and a supported CPU (roughly 2018 or newer for most business machines) — the upgrade is free. The work is in doing it properly: checking application compatibility, backing up first, scheduling around your business hours, and verifying everything works after.

2. Replace Hardware That Can't Upgrade

Many older PCs fail Windows 11's requirements and cannot officially upgrade. For machines in that category, replacement is usually the right call — and often overdue on performance grounds alone. A staged replacement plan spreads the cost over months instead of a single painful purchase, prioritizing the machines that handle sensitive data or critical work.

3. Buy Time with Extended Security Updates (ESU)

Microsoft offers paid Extended Security Updates for Windows 10 — security patches only, no new features or fixes — for up to three years for businesses, with published per-device pricing that roughly doubles each year. ESU is a bridge for machines you genuinely cannot migrate yet (for example, a PC tied to specialized equipment), not a long-term strategy. If you use it, pair it with a dated migration plan.

A Sensible Plan for a Small Business

1. Inventory: list every Windows machine and whether it is Windows 11-eligible. 2. Triage: eligible machines get scheduled upgrades; ineligible ones get replacement dates or a justified ESU exception. 3. Back up everything before touching anything. 4. Migrate in waves, testing your critical applications with the first wave. 5. Securely wipe and dispose of retired machines — old hard drives full of business data should never just go in a bin.

The Servers Are Next

If you are planning a Windows 10 transition, do the server inventory at the same time. Windows Server 2016 reaches its own end of support on January 13, 2027, and the two projects share a budget, a maintenance window and usually the same application compatibility questions. Doing them as one planned refresh is significantly cheaper than handling them as two separate emergencies. We cover the decision in detail in our guide to Windows Server 2016 end of support for Ontario businesses.

Don't Run This Project Alone

Some environments need extra care because a machine is welded to a piece of equipment. Medical and dental offices are the clearest example — an operatory workstation is tied to an imaging sensor whose driver may not be certified on Windows 11 yet, so the vendor has to be consulted before the upgrade rather than after it. We cover that specific situation in our dental office IT guide for Ontario practices.

This is a routine project for a managed IT provider and a disruptive one for a business trying to do it off the side of a desk. IT Rapid Support handles Windows 10 transitions for businesses across Toronto and the GTA — eligibility audit, upgrade scheduling, hardware recommendations and procurement guidance, Microsoft 365 and cloud moves where they make sense, data migration, and secure disposal. Call (289) 582-9930 for a straight answer on what your fleet needs.