This chapter discusses the broader spectrum of ability as part of the continuum of human competence. Thomas Armstrong’s theory regarding brain disorders is applied to all forms of disability as a means to better understand users with disabilities and how to design for them. Also discussed are the social factors influencing online and digital behaviors. Various assistive technologies and strategies are reviewed according to individual disabilities and conditions: blind, deaf, mobility, and cognitive impairments. The chapter includes a story that contextualizes the way digital outcasts are constantly adapting and evolving to meet emerging needs, ending with a case study about a stand-up comedian with cerebral palsy who uses an iPad to deliver his act.