Cities everywhere are struggling to adapt to demands of a changing climate as well as changes in resident expectations of environmental and spatial justice. This dissertation looks at urban transformation – fundamental change in one or more aspects of a city’s operation which triggers change in other aspects. To do so, it uses the social-ecological-technological systems (SETS) perspective to consider many aspects of the city as a complex adaptive system. It also employs as an analytical tool a framework developed to assess an urban system’s transformative capacity – the presence of multiple elements that may enable a desired transformation. It uses as a case study New Orleans, Louisiana’s efforts over its life to manage storm- and groundwater, and recent attempts to move the city toward accommodating water as an ecological reality rather than excluding it. Social influences on this technological manipulation of the ecology are key subjects of interest. Analysis of the city’s history indicates that parallel to heroic measures to remove water has been severe social inequality and inequity, characterized by exploitation of less powerful residents, extraction of their labor, and deferral of flood risk onto them. Ethnographic study of New Orleans over the time of fieldwork shows promising action towards new models of adaptation to water, and to greater social equality, in the form of infrastructural experiments, public education, and collective visioning. However, progress is blocked by powerful self-interested parties, maladaptive policies, and low political will. The population also experiences a great deal of cynicism and demands on attention, which causes divestment from the processes of equitable urban change. Lack of funding for new infrastructure is also a challenge, as it is in many U.S. cities, as comparative supporting research shows, among other findings. Final assessment is that New Orleans’ transformative capacity is low, but has some resources to improve. Recommendations include adding stronger equality and equity components to transformative capacity assessment, and that researchers and practitioners commit to long presence and activity in cities of interest. Future research should include assessments of more covert influences suppressing transformation, and disruptive means of adaptation.