Access to, and demand for, healthy and local foods is an issue that crosses numerous political, institutional, and disciplinary boundaries. Traditional philosophical approaches and market strategies have failed to provide stakeholders with the tools needed for addressing the entangled, systemic issues surrounding access to local and healthy food. In contrast, this article describes how a wicked problems1 (WP) framework along with a feminist pragmatist methodology are valuable for empowering students to collaborate with partners on wicked issues in our local communities. This framework encourages stakeholders to recognize the need for collaborative, context-sensitive, and iterative action processes aimed to meliorate current injustices. In particular, this article documents the philosophy behind, and initial outcomes of, Grand Valley State University students’ participatory action efforts designed to support the work of the Heartside Gleaning Initiative (HGI) in Grand Rapids, Michigan. The article ultimately highlights the philosophy behind such work, the structures and processes involved, as well as the challenges and benefits of an engaged, boundary-spanning educational model.