All UNESCO urban World Heritage sites are strictly regulated. In Antigua, Guatemala, this includes building façades and streets, as well as the use of public places. Homeowners and building owners, however, challenge regulations by using unapproved paints, signs, and building materials. Residents modify building façades to accommodate cars and open walls to effectively blend home-based businesses with the street. At the same time, street vendors contest regulated public spaces by behaving inappropriately by selling goods on public streets rather than designated marketplaces. Rather than conceive of property owners and vendors behavior as outside and in contrast to the building and street vending regulations, I reframe their actions within what I am calling urban spatial permissiveness, a concept I derive from Roy’s (2004) theory of the unmapping—flexible regulation—of urban space. Antigua offers an ethnographic setting that shows how regulations are not always rigidly enforced but are negotiated to deal with everyday contingencies that relate to residents’ and vendors’ rights to the city (Harvey 2008). By way of conclusion I consider Foucault’s concept of governmentality as a negotiated process, in order to argue that relationships between building regulations and public space usage reveal the limits of legality and strict enforcement policies.