Scholars of organizational paradox are becoming increasingly interested in how paradoxes become hierarchically related to or determined by other paradoxes, a relationship often referred to as “nesting.” While studies of nested paradoxes have begun to illuminate the interdependencies between complex social and organizational phenomena, there is still little consensus about the nature and the workings of nesting itself. To address this, we review the organizational paradox literature and develop a typology of approaches to theorizing nested paradox. Our typology concentrates on how studies describe two properties of nesting paradoxes: their empirical and theoretical continence. From these two continua, we argue that there are three general approaches to theorizing nesting. While two of these categories have already yielded extensive theorization, the category that understands nested paradoxes as both highly empirically and theoretically continent remains largely empty. This category, we argue, is the most ontologically oriented way of thinking about nested paradox and, consequently, is particularly powerful for explaining the emergence and failure of organizations through paradox itself. We illustrate the explanatory potential of this perspective by analyzing Wework’s dramatic rise and fall as an arrangement of nested paradoxes.