Monrovia’s unplanned settlements provide a window into the diverse rationales and practices that go into planning and managing urban space. Even though unplanned settlements are economically, spatially, and socially integrated into cities, the desire to eliminate or formalise them persists. In the essay, I examine how everyday risks are addressed in the coexistence and co-evolution of planning and unplanned urbanisation in postwar contexts. As well as showing how expert-recommended risk management approaches cross over into local practices, I explain how and why multiple understandings of ‘risk’ and ‘resilience’ can influence practice. The unequal power dynamic suggests that the practices of state actors influence the residents of unplanned settlements, in a manner that is discernible of governmentality. As riskscapes, and by extension resilience, represent multiple realities to stakeholders, the question of coalescing the mosaic of practices into a common risk governance framework is critical. The essay emphasises that resilience-building should evolve from a thorough understanding of the dynamics of the multiplicity of riskscapes. Finally, the paper argues that an evolutionary approach to risk governance, paying attention to the interacting elements and configurations that link discourse, actors, institutions, power, and knowledge, will provide a platform for negotiating the links between risk perception and risk assessment within the emerging riskscapes. This will be the basis of a deliberative and negotiated resilience pathway that will integrate the priorities and interests of all stakeholders in the planning and decision-making process.