In the light of increased organizational and environmental complexity, research turns ever more often to the notion of paradox to investigate how managers can navigate conflicting demands. However, the internal dynamics of paradox remain unclear, making it difficult to understand what exactly is meant by the concept, and how it can be managed in practice. This article notes that the full potential of paradox as an analytical tool for understanding complex situations of organizational life has not been reached, and reveals instances of organizational complexity that appear even more radical than current definitions of paradox posit. Using the sociologist Niklas Luhmann’s concepts of distinction and re-entry, we unfold the complexity of such situations and develop a typology that includes a novel type of paradox that appears underexplored. Illustrating several different ways that opposites can appear interdependent, interwoven, persistent, and synergistic, we contribute to theory- building within paradox research. Finally, we discuss our findings and managerial implications and point towards future research.