Rule enforcement is critical in democratic, self-governing societies. Many political disputes occur when citizens do not understand the fundamental rationales for enforcement (e.g., COVID-19 pandemic). We examined how naïve groups learn and develop wise enforcement systems. Based on theories from behavioral economics, political science, psychology, and education, we predicted that groups need to experience failure of an enforcement system, but be guided on restorative justice principles to collectively learn from this failure. Undergraduate students (N = 288) from a Midwestern U.S. metropolitan university self-governed a simulated common-pool resource with real financial payoffs. Groups began with one of three conditions designed to create different experiences with enforcement and regulatory failure: (a) no enforcement (no communication or peer sanctioning), (b) lax enforcement (communication with peer-sanctioning), or (c) regulatory abuse (peer sanctioning without communication). Half then received facilitated guidance on restorative justice principles (e.g., discuss whether/why to use sanctions). To examine cooperation, we measured how well participants maintained the resource. To examine group learning, we created a novel coding system, which tracked groups' constitutional decisions about conservation agreements and enforcement, conceptual understanding, and the enforcement systems they created. The no-enforcement and lax-enforcement conditions quickly yielded moderate cooperation via voluntary agreements. However, such agreements prevented groups from discovering how and why to use enforcement (peer sanctioning) to improve performance. Initial exposure to regulatory failure had different effects depending on facilitation. Unfacilitated groups fixated on initial misconceptions, causing them to abandon or create less sophisticated enforcement systems, hindering cooperation. Facilitated groups learned from prior failure-discovering principles of wise enforcement (e.g., collective efficiency, self-restraint)-and created more sophisticated enforcement systems (e.g., coordinated sanctions) that improved cooperation. Guidance on restorative justice principles and experience with regulatory abuse may be necessary preconditions for naïve individuals to understand and develop wiser collective enforcement systems.