Differentiated assessment of students with disabilities is required to determine vocational skills to plan for transition and employment. Quality differentiated assessment for transition requires a meaningful assessment of the tasks and the environment. This study examined a work setting that used a differentiated assessment process to evaluate student outcomes in an entrepreneurial setting where students were employed in a burrito stand on a school campus in preparation for competitive employment. Student participants were assessed in four broad areas that included hygiene, consumer service skills, management skills, and social skills. Participants included 30 students identified in various low-incidence disability categories such as autism, intellectual disability, and emotional disturbance. The students participated in a work setting for an academic school year, and data were gathered using the differentiated assessment developed. The study results indicated the use of differentiated assessment to measure student outcomes on the job and the reliance on the data obtained to make decisions appeared to be substantial factors in the students' ability to maintain employment. [ABSTRACT FROM AUTHOR]