Although enhancing the social competence of students with severe disabilities has long remained a prominent focus of school-based intervention efforts, relatively little attention has focused on identifying the most critical social and behavioral needs of students during high school. We examined the social skills and problem behaviors of 137 adolescents with severe disabilities from the vantage point of both special educators and parents. We sought to identify areas of potential intervention need, explore factors associated with social skill and problem behavior ratings, and examine the extent to which teachers and parents converged in their assessments of these needs. Our findings indicate teachers and parents of high school students with severe disabilities rated social skills as considerably below average and problem behaviors as above average. In addition, lower social skills ratings were evident for students with greater support needs, lower levels of overall adaptive behavior, and a special education label of autism. We found moderate consistency in the degree to which teachers and parents aligned in their assessments of both social skills and problem behavior. We offer recommendations for assessment and intervention focused on strengthening the social competence of adolescents with severe disabilities within secondary school classrooms, as well as promising avenues for future research.