This article describes how Circular Economy (CE) and Cradle to Cradle (C2C) can be used in university teaching to address these frameworks’ strengths and weaknesses in practice. The advantages of these frameworks for radical change are outlined, including their emphasis on upcycling rather than recycling (downcycling). This article discusses how students apply their understanding of transformative production frameworks to three case studies of products or materials. The student projects evaluating existing products in terms of their circularity value outline a number of practical as well as theoretical challenges. The case studies demonstrate that some products still have a long way to go to fully cycle materials within a closed system. Aside from illustrating the dangers of subversion of circular frameworks to the ‘business-as-usual’ scenarios, the assignments are instructive in showing how CE/C2C can be successfully taught. This article recommends pedagogical strategies involving both theory of sustainable production and sustainability and practical research into company’s operations in order to develop the students’ ability to meaningfully engage with CE/C2C models.