This paper describes cases of two adolescents with learning disabilities working in automotive repair businesses as part of a work-based education program. Neither adolescent was judged to have been successful by the workplace supervisors. The frameworks chosen for analyzing these cases draw upon recent work in self-determination, workplace learning, and negotiating accommodations for workers with disabilities. Data for the qualitative cases consist of interviews and detailed observations. Analysis, using a contextualist perspective, provides descriptions of the contexts for the two co-operative education placements and yields four themes that appear central to success in work-based education experiences for adolescents with learning disabilities: negotiating accommodations, routines, expectations, and preparation.