Over the 50 years since its publication, Ian McHarg’s Design with Nature has been enormously influential in shaping design and planning in cities and regions around the world, including in the flood-prone cities of New Orleans and Dhaka, Bangladesh. This commentary reviews the influence of Design with Nature in key plans and proposals in Dhaka and New Orleans to highlight the potentials and limitations of applying McHarg’s methods. In both cities, McHarg-influenced urban expansion plans of the 1970s and 1980s were largely not implemented because their focus on geophysical landscape processes did not address considerations of power, politics, and property. More recent green infrastructure proposals have threatened to entrench urban inequalities by labeling low-lying low-income settlements as against natural laws of landscape suitability. Drawing on these cases and on critical environmental scholarship produced in the years since Design with Nature, the commentary argues that McHarg’s work is essential for addressing contemporary urbanization challenges, but that it must be amended with a greater recognition of the politics of urbanization and environmental risk. To do so would require (1) expanding and problematizing the idea of nature, challenging the stable nature–society binary, and embracing pluralistic forms of environmental knowledge; (2) shifting from a conceptualization of design as “revelation” by technical experts to methods centered on synthesizing diverse perspectives and enabling democratic deliberation; and (3) recognizing that the shift to designing with nature is a politically fraught process in which adaptation opportunities and constraints are defined by place-specific historical patterns of urbanization.