When people think about threats to their business operations, they often imagine dramatic events — floods, fires, or extended power outages. But sometimes the biggest risks don’t come from natural disasters. They come from decisions about the technology your business uses every day.
One of those decisions is whether to keep using an older operating system once it stops receiving updates.
That’s exactly where many businesses are right now with Windows10. In just over two weeks, Microsoft will officially end free support for this operating system. This “end of life” stage has serious implications for CyberSecurity, business continuity, and long-term planning.
This guide will walk you through what this means, why it matters, and the steps you should take now to protect your business.
What “End of Life” Means for Windows10
When software reaches “end of life,” the company that makes it stops providing free updates, bug fixes, and technical support. For Windows10, Microsoft has announced that free support will officially end on October 14, 2025.
After that date:
• No more security updates — new vulnerabilities will not be patched.
• No bug fixes — any existing issues will remain unresolved.
• No official help from Microsoft — even if something critical breaks.
Your devices will still work, but they will slowly become less secure, less stable, and potentially incompatible with newer applications and tools.
Why This Puts Your Business at Risk
The most immediate concern is CyberSecurity. Once Windows10 stops receiving updates, every machine running it will become a more attractive target for cybercriminals.
Here’s why:
• Known vulnerabilities stay open — Attackers actively monitor end-of-life announcements and create tools to exploit older systems.
• Malware risk increases — Without regular patches, ransomware, viruses, and spyware have more opportunities to take hold.
• Compliance problems — Depending on your industry, running unsupported systems could mean failing to meet legal or regulatory security requirements.
• Network-wide exposure — Even if only one computer is affected, it can be used as a gateway to attack other systems on your network.
It’s a lot like leaving your office unlocked overnight — except in this case, the “door” is digital, and the break-in could happen from anywhere in the world.0
The Extended Security Updates Option — A Short-Term Fix
Some businesses may try to buy themselves more time with Microsoft’s Extended Security Updates (ESUs) program. This paid service offers security patches for a limited period after official support ends.
However, there are important limitations to understand:
• Cost increases every year — The longer you delay upgrading, the more expensive ESUs become.
• No new features or improvements — ESUs only cover security fixes; performance and compatibility issues remain.
• Short-term solution — ESUs are not a permanent option. Once they end, you must still upgrade.
For most businesses, ESUs are best treated as a temporary measure, not a strategy for the next five years.
Why Windows 11 Is the Recommended Upgrade Path
Upgrading from Windows10 to Windows 11 is the logical next step for most businesses.
Microsoft designed Windows 11 to be more secure and better suited to modern business operations. Key advantages include:
1. Stronger CyberSecurity features
• Built-in hardware-based security (such as TPM 2.0) to better defend against malware.
• Enhanced ransomware protection and phishing detection.
2. Improved productivity tools
• Better integration with Microsoft Teams and other collaboration tools.
• Enhanced multitasking features like Snap Layouts and virtual desktops.
3. Longer support cycle
• Ongoing updates and feature improvements for years to come, keeping your systems secure and current.
Potential Roadblocks to Upgrading
While the benefits are clear, upgrading isn’t always as simple as running an installer. Windows 11 has stricter hardware requirements than Windows10, which means:
• Older devices may not qualify — Systems without TPM 2.0, Secure Boot, or certain processors cannot upgrade directly.
• Performance concerns — Even if a device meets the minimum requirements, it might not perform well on Windows 11 if it’s several years old.
• Application compatibility — Some older software may need updates or replacements to work properly on the new OS.
Because of these factors, planning your transition in advance is critical.
Steps to Prepare for the Windows10 End-of-Life
If your business is still using Windows10, you should begin the upgrade process immediately. Here’s a step-by-step approach:
1. Inventory Your Devices
• Identify every device running Windows10 in your organisation.
• Note the hardware specifications and current software installed.
2. Check Windows 11 Compatibility
• Use Microsoft’s “PC Health Check” tool or similar utilities to see if each device can run Windows 11.
• Group devices into: Ready to Upgrade, Needs Upgrade, or Replacement Required.
3. Review Your Software
• Check whether your key business applications are fully compatible with Windows 11.
• Contact software vendors if you are unsure.
4. Create a Migration Plan
• Decide which devices will be upgraded, which will be replaced, and in what order.
• Factor in downtime, data backup, and staff training.
5. Back Up Your Data
• Use secure, verified backup methods before making any system changes.
• Consider an immutable backup solution to protect against ransomware.
6. Implement in Stages
• If possible, upgrade in phases to minimise disruption.
• Start with non-critical devices to test the process.
CyberSecurity Considerations During the Transition
The period between now and the end of Windows10 support is particularly risky. Cybercriminals often ramp up their attacks as software nears end-of-life.
Here’s how to strengthen your CyberSecurity posture during the changeover:
• Enable multi-factor authentication (MFA) on all accounts.
• Apply all pending Windows10 updates before support ends.
• Update third-party software to reduce vulnerabilities.
• Educate employees about phishing scams and suspicious downloads.
• Monitor network traffic for unusual activity.
By combining good planning with stronger CyberSecurity practices, you reduce the risk of an incident while your systems are in transition.
Why Waiting Could Cost More in the Long Run
Delaying your upgrade can lead to several hidden costs:
• Ransomware recovery expenses — Paying a ransom, restoring backups, and dealing with downtime.
• Lost productivity — Outdated systems are slower and more prone to crashing.
• Replacement in a rush — Emergency hardware purchases often cost more and leave less time for proper setup.
• Reputation damage — A breach involving outdated systems can undermine client trust.
Planning now avoids both financial and operational stress later.
Practical Tips for a Smooth Upgrade
If you’re preparing to move from Windows10 to Windows 11:
• Test critical workflows on a pilot machine before upgrading the whole company.
• Consider hardware leases if budget is tight — spreads out the cost of new equipment.
• Train staff on Windows 11 features to speed adoption.
• Use managed IT services to coordinate upgrades with minimal downtime.
The Bottom Line
The end of free support for Windows10 is more than just a technical deadline — it’s a major CyberSecurity milestone. Continuing to run an unsupported operating system exposes your business to preventable risks.
Whether you choose to upgrade to Windows 11 right away or use Microsoft’s Extended Security Updates for a short time, the key is to act before the deadline. Waiting until after support ends will leave your systems vulnerable and make the upgrade process more urgent — and likely more expensive.
About Robertson Technology Group
Robertson Technology Group, based in Victoria, BC, provides managed technology security and support solutions to small and medium-sized businesses across Canada. We take the burden of technology management off your shoulders, ensuring your systems are secure, reliable, and tailored to your needs.
Our local, client-focused approach means we work with your business, not against it — creating solutions that fit your workflow instead of forcing you to adapt to ours. With a flexible technology stack, we select the right combination of tools to maximise performance and CyberSecurity. Our pricing is customised for each client, and our personalised support ensures you’re never treated as just a number. We’re also exploring AI-driven risk analysis to strengthen security strategies for the future.