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This paper reviews the current theoretical scholarship on maladaptation and provides some specific case studies—in the Maldives, Ethiopia, South Africa, and Bangladesh—to advance the field by offering an improved conceptual understanding and more practice‐oriented insights. It notably highlights four main dimensions to assess the risk of maladaptation, that is, process, multiple drivers, temporal scales, and spatial scales. It also describes three examples of frameworks—the Pathways, the Precautionary, and the Assessment frameworks—that can help capture the risk of maladaptation on the ground. Both these conceptual and practical developments support the need for putting the risk of maladaptation at the top of the planning agenda. The paper argues that starting with the intention to avoid mistakes and not lock‐in detrimental effects of adaptation‐labeled initiatives is a first, key step to the wider process of …