The current case demonstrates the complexities of utilizing Youth Court as a restorative practice in an urban high school, by focusing on the complexities it presents for one student in particular. In this case, there are reasons why Youth Court clearly is not working at this particular school site as intended. However, more importantly for leadership preparation, the case surfaces dilemmas of cultural difference, teacher preparation, leadership preparation, and school policy that leaders must address prior to restorative implementation in order to ensure sustainable restorative practice moving forward.