Food deserts in low-income and underserved communities pose a significant challenge to ac- cessing healthy, affordable food, leading to poor health outcomes for residents. This project aimed to address this issue by examining the benefits and barriers that arise from connect- ing a student-run community garden (SRCG) with student-run free health clinics (SRFCs) to provide low-income patients with access to sustainable food and nutritional education. Using a case study research model, the study focused on investigating the organizational structure and potential mismatches between the two kinds of student-run systems. Birnbaum’s Higher Education Organization Framework (1992) was utilized to analyze how loosely and tightly coupled organizations can affect the success of collaboration. Vignettes were developed based on participants' observational experiences, and lessons were derived from fields and discussions with participants. The study identified several organizational barriers that complicated the re- lationships between student-run organic gardens and student-run free clinics. The SRCG was a loosely coupled organization with little centralized cybernetic control, and the lack of orga- nizational structure in SRCGs made it challenging to use SRFCs as outlets for providing fresh food to patients in the free clinics. Although connecting SRCGs and SRFCs shows promise for increasing food access and promoting health, the study found that it remains challeng- ing to use gardens as food production systems without creating a more cybernetically con- trolled structure in the SRCGs. By analyzing the benefits and barriers that arise from connecting these two organizations, this project sheds light on the potential of student-led initiatives to address health disparities and promote sustainable food systems in underserved communities.