Historically, students with disabilities experience less in-school preparation and postschool success compared with their peers without disabilities. U.S. federal legislation has evolved in an effort to promote successful in-school and postschool success for students with disabilities. Since 1990, legislation has emphasized the importance of postschool preparation (the Individuals with Disabilities Education Act), and more recently, the Every Student Succeeds Act of 2015 mandated all students be prepared for college and careers. In this article, we overview one court case ("Brown v. Board of Education") and seven pieces of pivotal legislation that had substantive impact on college and career readiness efforts. In addition, we discuss successes over time and suggest opportunities for change to enhance college and career readiness efforts.