An earlier generation of planners turned to Rittel & Webber’s 1973 conception of “wicked problems” to explain why conventional scientific approaches failed to solve problems of pluralistic urban societies. More recently, “complex systems” analysis has attracted planners as an innovative approach to understanding metropolitan dynamics and its social and environmental impacts. Given the renewed scholarly interest in wicked problems, we asked: how can planners use the complex systems approach to tackle wicked problems? We re-evaluate Rittel and Webber’s arguments through the lens of complex systems, which provide a novel way to redefine wicked problems and engage their otherwise intractable, zero-sum impasses. The complex systems framework acknowledges and builds an understanding around the factors that give rise to wicked problems: interaction, heterogeneity, feedback, neighbourhood effects, and collective interest traps. This affinity allows complex systems tools to engage wicked problems more explicitly and identify local or distributed interventions. This strategy aligns more closely with the nature of urban crises and social problems than the post-war scientific methodologies about which Rittel and Webber had grown increasingly sceptical. Despite this potential, planners have only belatedly and hesitantly engaged in complex systems analysis. The barriers are both methodological and theoretical, requiring creative, iterative problem framing. Complex systems thinking cannot “solve” or “tame” wicked problems. Instead, complex systems first characterize the nature of the wicked problems and explore plausible pathways that cannot always be anticipated and visualized without simulations. The intersection of wicked problems and complex systems presents a fertile domain to rethink our understanding of persistent social and environmental problems, to mediate the manifold conflicts over land and natural resources, and thus to restructure our planning approaches to such problems.