This case study details the NHS Board in Scotland's transition from Windows 10 to Windows 11, necessitated by the impending end of support for Windows 10 in October 2025. The Board, which serves over 400,000 citizens and operates a complex IT environment with multiple hospitals and healthcare facilities, faced significant challenges during this migration. XMA conducted a comprehensive readiness assessment to identify compatibility issues and developed a phased deployment plan aimed at minimizing disruption to healthcare services. The assessment included hardware and software inventory, compatibility testing, and evaluation of existing management solutions. XMA also provided strategic recommendations and implemented a Proof of Concept for Windows 11 deployment using Autopilot. The successful transition ensures that the NHS Board can continue delivering quality healthcare while enhancing security and management through modern practices. This case study outlines the critical steps taken to prepare the Board for future technological advancements.