Problem, research strategy, and findings: Cities experimented with street design to address health and economic impacts of the COVID pandemic between 2020 and 2023. Scholars have suggested that COVID represented a window of opportunity to transform aspects of urban planning, but the degree to which emergency interventions portend longer-term changes requires study. This study focused on street cafés as one of the more significant COVID-era street transformations. Street cafés are allocations of space in the cartway for outdoor dining. They introduce a social use to street space while increasing the complexity of managing street space. To assess the idea that the COVID crisis was a window of opportunity, we conducted a comparative case study of COVID street café programs in five North American cities. We drew on 16 interviews and analysis of policy documents to examine how street café programs were implemented, how they adapted existing policy and institutions, and whether their implementation represented a policy punctuation. Despite common objectives, implementing COVID street café programs played out differently in each case city. Urban form, existing policy, administration of emergency programs, and café design and experimentation all affected outcomes. These COVID-era programs led to one city initiating a new street café program; in two other cities, they accelerated implementation of recent policy initiatives, and the experience in the final two cities was ambiguous. Takeaway for practice: This research highlights the importance of recently adopted street policy in shaping emergency response. Although installation of COVID street cafés was widespread, planners will have to renegotiate emergency actions taken to lessen regulatory, administrative, and financial hurdles to café implementation to sustain viable street café programs in the long run.