This case study examines the struggles and successes of teachers and students collaborating with community organizations on the Second Tuesday Project, a community-based research and service program at an urban high school. Using qualitative methods, the study includes data from interviews, participant-observations, and focus groups to describe the experiences and perspectives of students and teachers participating in the Second Tuesday Project. Findings from the study highlight challenges with communication and curricular planning as well as successes with logistics and program flexibility. Implications for educators include the importance of clearly articulated goals, purposes, and guiding theories shared with all participants and a creative approach to removing logistical barriers between schools and communities. (Contains 1 endnote.)