As of May 2025, the Global Stat Counter reports that 53% of all Windows users are still running Windows 10, compared to the 43% running the newest Windows version, Windows 11(1). Despite its end-of-life date on October 14, 2025, these numbers indicate that a significant number of Windows users have not completed their migration to Windows 11. With Windows 10 support ending in the fall, businesses need to start preparing now.
What Does Windows 10 End of Life Mean?
According to Microsoft, after October 14, 2025, Windows 10 devices will no longer receive technical assistance, feature updates, or security patches(2). After that date, computers running Windows 10 will become increasingly vulnerable to threats, compatibility issues, and performance problems. Without these updates, organizations may also face regulatory compliance risks, higher IT costs for extended security updates, and challenges integrating with newer technologies.
Key Challenges and Strategies for a Smooth Transition
Upgrading to Windows 11 isn’t as simple as clicking “update.” There are critical steps and challenges organizations must address to ensure a seamless migration.
1. Hardware Requirements and Software Compatibility
Windows 11 has stricter hardware requirements, and many older devices will not support the upgrade. This means businesses may need to invest in new hardware that meets updated security, stability, and performance standards. Start by conducting a full device inventory to identify which systems meet Windows 11 requirements and which require upgrades or replacements. Planning early can help avoid unexpected budget overruns and supply chain delays.
In addition to hardware, software compatibility is a major consideration. Some legacy applications and custom infrastructure configurations may not be compatible with Windows 11. Businesses should evaluate their IT environments to determine whether software updates, replacements, or other workarounds are needed. Preemptive testing in a Windows 11 sandbox environment can help identify potential issues before full deployment.
2. Pilot Testing and Rollback Planning
To further mitigate the risk of running into compatibility issues and other critical errors, organizations should consider creating a pilot group to test Windows 11, then gradually expand the deployment based on business priorities and IT capacity. When doing so, management should ensure a robust rollback option is in place to minimize the risks surrounding critical issues or failures.
3. Ongoing Security Measures
As with any major IT infrastructure change, on-going reviews and evaluations can minimize security risk and ensure success. We recommend (1) establishing a regular schedule for security audits and vulnerability assessments to address emerging cyber threats, (2) implementing continuous monitoring of systems, and (3) maintaining a patch and vulnerability management program to ensure latest security patches and updates are applied to all devices.
We’re Here to Help
Navigating the transition from Windows 10 to Windows 11 comes with a variety of risks, but a well-planned strategy and adequate preparation can help organizations avoid unnecessary costs and minimize business impact.
If your organization has any questions about how to manage these risks and prepare for migration, Herbein’s Risk Management Practice has dedicated professionals who specialize in tailored risk management solutions to help businesses stay secure and compliant.
Learn more about our cybersecurity services and get in touch with our Risk Management team today.
Article Contributed by Melissa Gallo
