Individuals with disabilities are less likely than their peers without disabilities to be employed or enrolled in postsecondary education. Even with federal legislation efforts designed to provide targeted supports to this population, the discrepancy persists. Students with disabilities who attend schools in rural settings may experience additional barriers to employment and postsecondary enrollment not faced by those in urban and suburban locales. This article reviews post-school outcomes and barriers that youth with disabilities in rural areas may encounter. These may include concerns related to transportation, limited opportunities, and varied perceptions on the value of higher education. In addition, special educators in rural schools may have limited training opportunities and a wide range of position responsibilities that require expertise in many areas. Then, to help address these discrepancies, strategies to support students and improve services are presented in four broad areas, including (a) augmenting teacher training and practice, (b) partnering with vocational rehabilitation, (c) improving public policy, and (d) leveraging the strengths of rural communities.