Published by Pund-IT 

Windows 10 reaches end of support on October 14, 2025. After that date, devices on Windows 10 will no longer receive security fixes or feature updates from Microsoft. For Ontario small and mid-sized businesses, this isn’t just an IT milestone—it’s a security and continuity decision that affects risk, compliance posture, and day-to-day productivity. Microsoft Support

What “End of Support” actually means

• No more security updates or bug fixes from Microsoft.

   

• Increased exposure to ransomware and other threats over time.

   

• Certain Microsoft apps and integrations will gradually lose support and reliability on Windows 10. Microsoft Support
  

   

Keep in mind: Microsoft’s Extended Security Updates (ESU) can provide time-limited security updates past October 2025, but ESU is a safety net, not a long-term strategy. 

Why it matters for Ontario businesses

Ontario organizations handle customer and employee data subject to Canadian privacy laws. Running unsupported operating systems increases risk exposure and may complicate cyber-insurance obligations. Proactive planning now reduces security risk, upgrade rush costs, and downtime later.

A simple, low-friction plan

1) Assess what you have

Create a current inventory of laptops and desktops: age, role, warranty status, and whether each device is likely Windows 11-capable.

• Check official Windows 11 hardware requirements (CPU, TPM 2.0, UEFI/Secure Boot, RAM, storage). Microsoft – Microsoft Learn
  

   

• Use Microsoft’s PC Health Check to verify eligibility on a per-device basis. Microsoft Support
  

   

2) Decide: upgrade vs. refresh

• Windows 11 in-place upgrade: Best for devices that meet requirements and are in good health.

   

• Hardware refresh: For older or borderline machines, replacement is often more reliable and cost-effective than investing in stopgaps.

   

How Pund-IT helps
For our managed clients, we handle hardware refresh and procurement, imaging, device configuration, and warranty tracking, so you stay current without the scramble.

3) Build a staged rollout (avoid the “big-bang”)

• Pilot with a small group → incorporate feedback → expand by department or location.

   

• Schedule cutovers after hours to minimize disruption.

   

• Provide quick-hit user guidance (what’s new in Windows 11, where common settings moved, etc.).

   

4) Protect data and maintain continuity

• Ensure reliable backups before any migration. Pund-IT’s Kopi series covers full-system images, file-level protection, and cloud-to-cloud backups (Microsoft 365/Google Workspace) so rollbacks are quick if needed.

   

• Document restore points and test them, restore testing is part of real resilience.

   

5) Modernize security as you move

• Pair upgrades with essential controls: endpoint protection (e.g., AnzenXDR), DNS-layer filtering (AnzenDNS), and email threat protection (AnzenEdge/Sentinel).

   

• Align device baselines (BitLocker, Secure Boot, least-privilege, patch cadence) as part of your Windows 11 standard.

   

6) Use ESU only as a short-term safety net

If a subset of devices must remain on Windows 10 temporarily (regulatory app, vendor dependency, or timing), enroll them in Microsoft ESU while you complete your transition plan. ESU extends critical and important security updates, but it’s temporary and should run alongside a firm migration timeline. Microsoft Learn

Helpful Microsoft references

• Windows 10 end of support overview (official) — what EOL means and timelines. Microsoft Support
  

   

• Windows 11 system requirements — official minimums and details. Microsoft
  

   

• Windows 10 ESU program — how ESU works for organizations. Microsoft Learn
  

   

How Pund-IT can help

• Readiness assessment: inventory, eligibility, and a right-sized rollout plan.

   

• Procurement & lifecycle: device refresh for managed clients, W11-ready standards, warranty coordination.

   

• Migration delivery: imaging, deployment, data migration, and user handoff with minimal downtime.

   

• Resilience & security: Kopi backups + Anzen security stack to keep your team productive and protected.

   

Contact us if you need support. We’ll help you plan and execute a smooth move to Windows 11—without the rush or the risk.