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As urban environments face increasing energy consumption demands, researchers in architecture and urbanism are becoming increasingly eager to reduce cities’ ecological footprints through innovative architectural and urban development strategies. In this context, we developed a digital device to evaluate and simulate rooftop potential. This research involved exploratory studies of rooftops in three cities: Chicago, Montreal, and Paris. We selected three abandoned buildings to regenerate, beginning with their rooftops. In each case, the rooftop was approached as a space for experimentation aimed at addressing urban issues specifically reducing the urban heat island effect and managing rainwater. One particularly exciting aspect of our research was the study of a historic post office in Chicago, famously featured as the Gotham City bank in the Batman movies. This connection to popular culture has added a new layer of identity to the building, blending historical significance with contemporary relevance. Overall, the strategies identified through this work aim to empower cities and help reduce their dependence on fossil fuels.