As Windows 10 approaches its end-of-life, Ontario businesses face a pivotal decision: upgrade to Windows 11 or risk exposing their systems to growing security vulnerabilities. While legacy systems may continue to function, the absence of regular patches means the safety net is gone—and cyber threats are waiting to pounce.
Microsoft will officially end support for Windows 10 on October 14, 2025. That means:
Cybercriminals often target outdated systems. The infamous WannaCry ransomware attack exploited a known vulnerability in older Windows versions—costing businesses millions in downtime and recovery.
With the deadline fast approaching, here are the most pressing issues Ontario businesses should be aware of:
Free Upgrade Window Is Closing
Businesses still running Windows 10 may qualify for free upgrades—but time is running out. Delaying could mean paying out-of-pocket for licenses later.
TPM 2.0 Hardware Requirements
Windows 11 requires Trusted Platform Module (TPM) 2.0, which many older devices lack. IT teams across Ontario are conducting hardware audits to identify upgradeable machines.
Enhanced Security Features
Windows 11 introduces passwordless authentication, virtualization-based security (VBS), and ransomware protection—critical for industries with strict data compliance needs.
Deployment Challenges for Enterprises
Recent updates have caused issues in enterprise environments using WSUS/SCCM. IT partners are helping businesses test and validate updates before full deployment.
Funding Opportunities
Ontario and federal programs offer grants for digital modernization. These can help offset hardware and software upgrade costs—especially for SMBs.
Many Ontario-based companies are already planning their transition. For example:
Upgrading doesn’t have to mean breaking the bank. Here’s how Ontario businesses can ease into Windows 11:
Assess Hardware Readiness
Use tools like Microsoft’s PC Health Check to identify which devices meet Windows 11 requirements.
Stagger the Rollout
Start with critical departments and expand gradually to minimize disruption and spread costs.
Use Refurbished or Certified Pre-Owned Devices
Many vendors offer Windows 11-ready machines at reduced prices.
Apply for Grants or Tax Incentives
Keep an eye on Ontario’s business support portal for funding updates.
A trusted IT support partner can make the transition smoother, smarter, and more cost-effective. Here’s how:
Hardware Lifecycle Reports
Identify which devices are eligible for free upgrades and which need replacing—prioritizing high-risk endpoints.
Upgrade Planning & Roadmaps
Create a phased rollout strategy tailored to your business size, industry, and budget.
Security Audits
Assess vulnerabilities in legacy systems and recommend patching or migration paths.
License Optimization
Ensure you're not overspending on software licenses—especially during transitions.
Staff Training & Support
Help your team adapt to Windows 11 with onboarding sessions and ongoing helpdesk support.
Cloud Integration
Assist with migrating to Microsoft 365 or Azure services to future-proof your infrastructure.
| 🔒 Benefit | 💡 Why It Matters |
|---|---|
| Closes Known Vulnerabilities | Prevents attackers from exploiting outdated code |
| Ensures Compliance | Meets industry regulations for data protection |
| Improves Stability | Reduces crashes and performance issues |
| Enables Threat Detection | Modern OS versions include real-time security features |
We know businesses have enough on their plate so we are doing everything we can to take the planning and budgeting stress off of our clients. Also to communicate that there is not one size fits all response to the Windows 11 upgrade and we are here to help your business create the most efficient plan to stay protected during the upgrade.
Whether you're a small business in Cobourg or a growing enterprise in Whitby, we’re here to help. Our team specializes in Windows 11 migration planning, hardware assessments, and security-first strategies tailored to Ontario businesses. Call us at 416-900-6047 or email info@attitudeit.ca