Teacher education programs that focus on preparing urban elementary school educators face a daunting task. In a relatively short time, roughly four semesters of coursework, students are prepared to be transformed into teachers who are certified to meet the challenges of urban schools. This transformation occurs from the outside in as they learn culturally responsive pedagogy, effective strategies for classroom management, instructional design, assessment, and develop strong content knowledge in literacy, mathematics, science, and social studies. At the same, they must be transformed from the inside out, developing the dispositions and identity of an urban educator. To maximize development within program confines, it is essential that every assignment in every course be relevant and powerful with elements that facilitate both content and disposition development. The authors decided to study how this happens with pre-service teachers in the context of a reading methods course. Accordingly, the authors' purpose was to examine the use of a case study assignment in a reading methods course for elementary and early childhood pre-service teachers preparing to be urban educators. They sought to identify elements that resulted in outside in/inside out development as well as those that were not functioning as designed. (Contains 1 table.)