Unlike the traditional disciplinary approach to research and problem-solving still common in higher education, this article explicates and recommends an interdisciplinary, holistic pedagogical approach that takes seriously the interconnectedness of our wicked social sustainability challenges (e.g., poverty, global climate change, food access, among others). We argue that educators can better prepare students to tackle such wicked problems by requiring they engage with locally based problems connected to large-scale systemic challenges. By discussing the design and outcomes of the course “Wicked Problems of Sustainability” from both the students’ and instructor’s perspectives, we seek to extend and enhance effective pedagogical strategies. As a laboratory for sustainability education and innovation we have developed a transdisciplinary, community-engaged, upper-division undergraduate course that engages students in participatory research on the inextricably linked dimensions of social sustainability. Collaborating with community partners to work across networks, disciplines, and institutions, students have the opportunity to ameliorate real problems in the local community. In doing so, the course confronts students and the instructor with a series of robust challenges from intensive collaborations, to logistical and time-management dilemmas, to real-world execution issues. This article details the obstacles associated with messy inquiry, participatory research, and community engagement and provides recommendations for overcoming them.