Windows 10 End of Life: Should You Migrate to Windows 11 Now?

With the Windows 10 end-of-life deadline approaching in October 2025, businesses face a crucial decision. After this date, Microsoft will stop providing essential updates, security patches and technical support for the operating system. This means that systems running on Windows 10 will be left without critical protections, making them vulnerable to security threats, performance issues and compliance risks. Your PC or point-of-sale terminal will no longer receive updates that keep it secure and running smoothly.

Windows 10 “End-of-Life” Impact on Businesses

Businesses rely on seamless integration across their systems to maintain efficiency and productivity. Outdated software disrupts this ecosystem, leading to significant challenges like system downtime during critical hours, legacy applications struggling with compatibility issues and broken integrations with essential tools like CRM platforms, finance systems or supply chain solutions. Additionally, employee productivity suffers when collaboration features are unavailable, making it harder to streamline workflows and maintain business continuity.  

Before Windows 10 goes ‘end-of-life’ on October 14^th 2025, businesses will need to make a decision on how to move forward. Once support ends, Microsoft will no longer provide security updates or patches, making systems increasingly vulnerable. Think of it like driving a car without seatbelts: you’re exposed to risks with no safety net. For Windows 10, this means:

• No more security fixes: Unpatched vulnerabilities become easy targets for cybercriminals.
• Compliance gaps: Businesses handling payment data (e.g., Payment Card Industry Data Security Standard – PCI DSS) could face fines for unsupported software.

• Stagnant productivity: Newer Windows versions offer speed boosts, AI tools and features like Windows Copilot to streamline workflows.

The Broader Implications: Cyber Insurance, Compliance and Hardware Challenges

Beyond security and productivity risks, failing to migrate from Windows 10 can also jeopardise your business’s cyber insurance and compliance standing. Insurance providers may require that businesses maintain up-to-date software to remain covered. If your systems run on unsupported versions of Windows, you may find it difficult to claim insurance or face higher premiums due to increased cyber risks. Additionally, maintaining PCI DSS compliance becomes increasingly difficult without the latest security patches, leaving you exposed to potential fines or breaches.

Migrating to Windows 11 isn’t just about updating your operating system. As Windows 10 nears end-of-life, the hardware running it will also start to show its age. Some devices may not support Windows 11, and businesses should factor in hardware upgrades as part of the migration process. Barron McCann provides seamless end-to-end hardware upgrade services, from onsite upgrades and rollouts to endpoint management, ensuring businesses of any scale and device volume stay ahead without disruption. This can require additional planning and budget, especially for businesses that rely on POS systems or specialised hardware that might not be compatible with newer versions of Windows.

What Should Businesses Do?

Businesses should begin migrating to the latest Windows version as soon as possible. Upgrading offers key security improvements, such as Smart App Control and better compliance with standards like PCI DSS. Features like Snap Layouts and Virtual Desktops help teams manage tasks efficiently, balancing efficiency, productivity and security. To ensure a smooth transition, start by evaluating your current systems; assessing applications, hardware compatibility and configurations. A phased rollout during quieter periods, along with testing in batches, can reduce disruptions. Post-migration support and staff training will help your team adapt quickly.

Retail Assist has helped many businesses navigate their Windows migration process with ease, ensuring minimal disruption and maintaining normal business across all stores. If you need support with your migration, Retail Assist can provide this expertise to ensure a smooth transition.

Migrate Before the October Deadline

Delaying your Windows 10 migration can lead to costly mistakes, from system misconfigurations to last-minute expenses. To facilitate a smooth transition to Windows 11, Microsoft is offering a series of informative webinars led by M365 technical specialists and global Microsoft training partners. These 60-minute sessions will equip businesses with the knowledge needed to navigate the upgrade process effectively.

Alternatively, we can help simplify this entire process and ensure your transition is seamless with a detailed migration assessment where our experts will audit your systems and create a tailored, cost-effective plan. Once the roadmap is set, you can schedule your upgrade at a time that works for your operations, allowing your team to focus on peak-season strategies or holiday preparations while we handle the technical details. To keep your systems running smoothly long-term, consider having a conversation with our managed services team for ongoing updates, monitoring and strategic IT support.

Outdated software should never disrupt your busiest season. Talk to us to schedule your Windows 10 migration before the October 14 deadline.