This chapter argues that architectural judgment is best understood and practiced as a public conversation through which we shape our material, social, and ecological conditions. It outline four characteristics of public conversation essential to the success of regenerative design and identify capacities required of facilitators and participants in these conversations. It then demonstrates that such regenerative dialogue is, indeed, possible, drawing from research in various social sciences and examples from regenerative design practice. The chapter also offers propositions from the emerging scholarship and practice of regenerative design as partial answers to these core challenges for architectural judgment, drawing primarily from three recent inquiries: We see promise for the future of regenerative design in architectural judgment, yet we also observe significant challenges. Our research identifies two primary obstacles to achieving regenerative design within conventional architectural discourse: it is both too exclusive, and too narrow.