The end of Windows 10 support is approaching, prompting IT decision-makers to consider transitioning to Windows 11. This transition allows organizations to modernize hardware, rethink client infrastructure, and adopt advanced management technologies. Continuing to use Windows 10 can lead to high maintenance costs and potential performance issues with M365/Office applications after October 14, 2025. Upgrading to AI-capable PCs can enhance operational efficiencies, while unsupported systems expose organizations to cyber threats and compliance risks. Windows 11 Pro offers improved security features, and upgrading aligns with sustainability goals through practices like Asset Recovery Services. A well-planned transition strategy is essential to avoid rushed decisions and ensure compatibility and training. Delaying the upgrade poses risks, including financial burdens from extended security update fees.