Why Businesses Still Struggle with Windows 11 Upgrade Challenges

Many sectors face Windows 11 upgrade challenges as they move from Windows 10, with healthcare and industry struggling due to hardware and software compatibility issues

As enterprises respond to the end of life of Windows 10 and transition to Microsoft’s newest platform, many are discovering unexpected Windows 11 upgrade challenges. While most organizations are making steady progress, industries that rely on specialized hardware — such as healthcare, industrial manufacturing, and maritime operations — are finding the transition far more difficult than anticipated.

Healthcare Faces Expensive Windows 11 Upgrade Challenges

A report from Digital Health News highlighted that the UK’s Rotherham Health Trust successfully upgraded most of its systems to Windows 11. However, the authority hit a major obstacle when a portion of its devices failed to meet the operating system’s compatibility requirements.

According to the report, the Trust faced a costly bill of £25,000 (about $32,900) to make a three-year-old machine compatible. This situation underlines how Windows 11 upgrade challenges can quickly become financial burdens when specialized medical devices are involved.

The problem isn’t isolated. Posts on Windows Forum revealed that several clinical software suppliers have refused or failed to certify their programs for Windows 11. Without certification, healthcare organizations cannot complete the upgrade without risking system failures or violating compliance standards.

Compatibility Issues Add to the Complexity

Gartner director analyst Timon Watson explained that medical environments make upgrades particularly difficult because of their complexity. “These devices operate on isolated networks with no outside access and require dedicated management tools,” he said. “Any changes demand extensive testing and validation that can take months.”

Watson also emphasized that many of these systems are tied to equipment sold and maintained by vendors. This means that any Windows 11 upgrade challenges often involve expensive vendor support or hardware replacement — costs that can stretch into the thousands or even millions, especially for MRI scanners and X-ray systems.

Industrial Vendors Also Struggle with Windows 11 Compatibility

The healthcare industry isn’t the only one grappling with the issue. Rockwell Automation recently warned that its ASEM 6300P and 6300B industrial computers are generally not compatible with Windows 11 due to older processors. Similar compatibility concerns are expected across other industrial sectors, as legacy hardware cannot always meet the system requirements of the new OS.

Maritime Sector Slow to Respond to Windows 11 Upgrade Challenges

Beyond healthcare and manufacturing, the maritime industry is also lagging behind. Research from Marlink found that nearly half of all shipping vessels have yet to upgrade from Windows 10. This delay could expose fleets to potential cybersecurity threats as Microsoft phases out support for the older operating system.

However, Gartner security specialist Chris Silva noted that the risks aren’t immediate. Third-party vendors continue to offer extended security services for legacy systems, allowing companies more time to plan their Windows 11 upgrade challenges strategically.

Microsoft Extends Support with Windows 10 IoT Enterprise

To ease the transition, Microsoft introduced Windows 10 IoT Enterprise, which will receive updates until 2032. This solution gives organizations with embedded or industrial systems a way to remain secure without fully migrating right away.

For businesses still deciding their next steps, the Windows 11 upgrade challenges highlight the need for thorough planning. Evaluating hardware compatibility, vendor certification, and total cost of ownership will be key to achieving a smooth and secure migration in the years ahead.