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The importance of inscribing maintenance and continuity — disruption mitigation — measures into Smart City technology has long been an overlooked topic in proposals and procurement processes, hampered in part by lack of legibility, advocacy, and community capacity for addressing innovation. The paper analyzed four select cases from the Top 20 finalists of Infrastructure Canada’s Smart Cities Challenge by asking the question, ‘what happens when innovators move on?’. Cases focused on the themes of intergenerational knowledge, food security, test-bed urbanism, and disaster response. Case specific examinations were synthesized into broader explorations regarding addressing underlying infrastructure, labour force availability & training, and the role of government and planners in these projects. Finally, future research recommendations discuss how to package site specific maintenance and continuity measures into Smart City projects such that communities are equipped to assume systems from the innovators.