The use of assistive technology in special education has grown over the past four decades. In inclusive settings, assistive technology plays a vital role in providing access to academic content for students with disabilities. As the role of assistive technology in secondary classrooms expands, concerns regarding student autonomy, personal preferences, and the societal implications associated with certain tools increase in significance. This article outlines important considerations for teachers to factor in when making assistive technology selections and identifies three decision-making evaluation tools to aid in the selection process for secondary students with disabilities.