Obstacles encountered by young adults with intellectual disability (ID) during the transition from high school to post-school employment have great potential to limit an individual's opportunity and/or capacity for self-determination with regard to employment. This qualitative study examines the challenges to self-determination experienced by a group of nine interns with ID during a one-year Project SEARCH internship program in a Kentucky distribution center. Through field observations, interviews, photographs, goal-reporting, and administration of the "AIR Self-Determination Scale," challenges to self-determination were identified. These included challenges related to communication; social competence in the workplace; work skill development; emotional regulation; and seeing oneself outside of the current work experience. Workplace interactions, experiences, instructional strategies, and individualized supports were implemented collaboratively among interns, supervisors, co-workers, instructor, and employment specialist during the program year. As a result, interns demonstrated positive growth and development in the characteristics of self-determined people related to the identified challenges.