Summer camp can be a setting for positive youth development, yet more understanding is needed about how camps measure youth development outcomes. The purpose of this study was to examine the experiences of The Hole in the Wall Gang Camp--a medical specialty camp-- using the American Camp Association's Youth Outcomes Battery (YOB) over six years. In this case study, we examined challenges and successes in the use of the YOB to measure friendship skills, interest in exploration, and independence, and how findings from evaluation studies were used to improve camp practice. Data were analyzed from evaluation reports, participant observations of internal staff gatherings and communications, and document review. Results revealed lessons learned about scheduling data collection and contemplation of intentional outcomes, ease in YOB usage, and utility for stakeholder communications and program improvement.