Disabled individuals have achieved progressive improvements in their daily lives through the advancement of assistive technology throughout the centuries. The evolution of assistive devices from ancient canes and trumpets to the latest AI-powered tools represents the technological advancement of assistance for disabled individuals. The evolution of assistive technology for disabled individuals splits into three distinct eras: the Foundation Period (before 1900) cantered on basic assistance devices followed by the Establishment Period (1900–1972) focused on regulatory frameworks then the Empowerment Period (1973–present) marked the integration of smart assistive technologies from basic machinery to advanced AI-driven digital innovations. This chapter explores the integration of AI technology that has made tremendous advancements in assistive services for disabilities. This chapter explains the historical transformation in assistive technology for disabled individuals from ancient aids to modern AI-based solutions that is from the initial stage of hearing aids and Braille systems and wheelchairs come the latest AI-driven solutions including brain-computer interfaces and computer mobility tools. The chapter reveals the trend toward popular assistive technologies which have become both intelligent and adaptive and personalized through the examination of their advancements. Through this development, AI shapes the way disabled people interact with present-day technology systems.