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This paper introduces the notion of ‘future-proofing’ to describe how urban futures are made in the Southeast Asian global city-state of Singapore through methods of design that become articulated as political possibilities. It seeks to add to STS literature on the production of futures as sociotechnical imaginaries (Jasanoff and Kim 2013), and the examination of future-making practices as an “anthropology of the Meantime” (Fischer 2018) that moves “between the fantasies of nostalgia and apocalypse.” I present three brief ethnographic episodes from 2015, the year when Singapore marked fifty years of postcolonial independence, that reflect three modes of urban future-making: 1) the ‘event-scape’ of The Future of US, a government-driven public exhibition held in a large installation of geodesic domes that targeted Singaporean audiences with an immersive vision of a hi-tech future, which, in making an intergenerational claim, gestures back to the city-state’s moment of achieving independence in 1965; 2) design-making sessions conducted in the Singapore makerspace Sustainable Living Lab that taught methods of future-casting and design thinking to members of the public; and 3) discussions of potential collaborations between complexity scientists and researcher-officials from a Singapore government-run urban thinktank. These episodes demonstrate Singaporean future-proofing as post-apocalyptic utopian performances of entrepreneurial rationality pivoted around a notion of limitation, which oscillate between techno-utopian projection, and pragmatic problem-solving that returns to the past and/or a formula, with regards to the city-state’s collective future.