Microsoft will cease free support for Windows 10 on October 14, 2025. Continuing to use Windows 10 after this date will incur significant additional support costs through the Extended Security Updates (ESU) program, which doubles fees each subsequent year. A one-year ESU option extends support only until October 2026. Organizations face challenges such as increased support costs, outdated technology, cybersecurity risks, and lack of AI integration. Transitioning to Windows 11 Pro devices with advanced technology is essential for maintaining competitiveness and productivity. A seamless device refresh strategy should include assessing current assets, budget planning, establishing an implementation timeline, and providing training and support for staff.