Campus outdoor recreation programs can play an integral role in developing student leaders. In this study, we sought a better understanding of the shared positive elements exemplary outdoor programs are using to develop their student leaders. The study was designed using a collective case study methodology and the theoretical lens of the Leadership Identity Development (LID) model. Representatives from five exemplary outdoor programs were interviewed with an appreciative inquiry approach. Five common themes emerged from the data: (a) Institutional Support, (b) Transformative Experiences, (c) Meaningful Culture, (d) Facilitative Structures, and (e) the Keys to the Castle: Authentic Leadership Opportunities. Themes were interrelated and contributed to an overall understanding of the environment that allows for successful leadership development in campus outdoor programs.