This research was designed to understand current school gardening efforts in Pinellas County, Florida. School gardens have become an important aspect of experiential learning and nutrition education in schools throughout the United States. Many not-for-profit organizations have attempted to increase the prevalence and efficacy of school garden programs as a means of providing educational opportunities and working to curb diet-related health issues in children. Most of these organizations are seen as apolitical in nature, because they access mainly private sector funding sources and volunteer support. This provides flexibility for these social projects, but also takes pressure off of the state to support school food and nutrition education efforts and reinforces neoliberal ideas about food systems. Paradoxically, strict public school standards and measures of success as a result of neoliberal education reform often prevent teachers and school administrators from utilizing these school gardens fully, and from using them as a sufficient means to fully discuss nutrition, healthy eating, and local food (instead focusing on other topics that fit more closely with state-regulated education standards). This research analyzed one such organization in Florida that installs gardens in “failing” Title I schools. Ethnographic research was conducted with these two organizations in an attempt to uncover some of the infrastructural challenges faced and uses a comparative approach to offer critical insights, suggestions for improvements, and best practices for navigating these challenges as determined by teachers, school administrators, and organization staff and volunteers.