The purpose of this article is to identify legal issues concerning the transition planning process through a qualitative analysis of administrative and judicial decisions addressing transition services for students with disabilities. The issues that emerged from the analysis were categorized into five prevalent themes: agency contacts, student involvement, individualization of the transition plan, district obligations, and appropriateness of the transition plan. The themes included both procedural and substantive components. Changes in the newly reauthorized Individuals with Disabilities Education Act are discussed, and implications for policy and practice are presented.