Although early work experiences during high school represent one of the most consistent predictors of postschool employment for young adults with disabilities, little is known about how these adolescents might access these valuable transition experiences. This study examined the summer employment and community activities of 136 high school students with severe disabilities. The majority of youth was either not working (61.7%) or reported sheltered employment (11.1%). The most prominent predictors of summer employment status were holding a job during the spring semester and teacher expectations for employment. Recommendations for research and practice focus on increasing the capacity of schools, families, and communities to support the involvement of youth with severe disabilities in meaningful summer activities.