Urban agriculture initiatives are on the rise, providing healthy food while teaching a land ethic to youth. In parallel, increasing numbers of university graduates are obtaining Extension work requiring the effective communication of science in a diverse, urban, low-income setting. This study evaluates a pilot service-learning program, the Community Food Security Scholars program, designed to teach students the complexities of urban food security issues while they acquire basic agriculture production skills. By analyzing student responses in pre- and post-service interviews, the authors evaluated students’ interaction with the diverse and economically disadvantaged populations, with which many of the students had little previous experience. Results revealed that although students felt they gained valuable theoretical and experiential knowledge about food access, they also faced challenges interacting with community members, possibly affecting the project’s learning outcomes. The evaluation resulted in a new course with enhanced opportunities for cultural competency training and outreach.