Traditional, theoretical pedagogical practices based in disciplinary expertise generally fail to prepare students for high-stakes, public problems. In contrast, “Wicked Problems of Sustainability” is an undergraduate course designed to provide students with the opportunity to redress complex, local problems through an experiential, community-engaged model. By implementing pedagogy developed through the integration of a feminist pragmatist framework with the literature on wicked problems, this course offers opportunities to impact real problems, develop skills, and foster virtues necessary for tackling public problems. Given the value of this work, but also the difficulties, this article highlights the potential pitfalls of community work on wicked problems in addition to providing a series of recommendations for a pragmatic, community-based, experiential pedagogy in a “wicked” world.