This paper describes cases of two adolescents with learning disabilities working in automotive repair businesses as part of a workbased 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 selfdetermination, 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