Underpinned by the new world Kirkpatrick model and in the context of a community-based, sport psychology program (My Strengths Training for Life™) for young people experiencing homelessness, this process evaluation investigated: (1) young peoples’ reactions (program and facilitator evaluation, enjoyment, attendance, and engagement) to and learning (mental skills and transfer intention), (2) the relationship between reaction and learning variables, and (3) the mediators underpinning this relationship. 301 young people living in a West Midlands housing service completed questionnaires on demographics, reaction and learning variables. Higher levels of program engagement were positively associated with more favorable reactions to the program. Enjoyment positively predicted learning outcomes, which was mediated by transfer intention. Recommendations are made for: (1) a balance between rigor and flexibility for evaluation methods with disadvantaged youth, (2) including engagement as well as attendance for indicators of meaningful program participation, (3) measuring program experiences (e.g., enjoyment) to understand program effectiveness, and (4) providing opportunities for skill transfer during and after program participation. Findings have implications for researchers, program commissioners, and policy makers working designing and evaluating programs in community-based settings.