The evolution of COVID-19 in Italy brought major impacts in social and psychological terms. These impacts have been accelerated by the urban planning approaches applied in the contemporary development of Italian cities (1960-today). The most zoned territories, those with the least amount of green space and those with the fewest neighborhood groceries have suffered heavily the effects from the pandemic. On a building scale, moreover, the absence of common spaces and the smallness of housing units further exacerbated the social and individual effects of the lockdown. These urban planning patterns proved to be particularly ineffective in coping with an unforeseen extreme event, and thus require extensive rethinking. We can derive an important lesson from these failures also to reflect on climate change adaptation.