Laws governing street vending in New York City are confusing, convoluted, at times contradictory and difficult to enforce with any sort of consistency. In this context of uncertainty and illegibility, the practice of street vending in New York and particularly in central areas of Manhattan, is managed in decentralized, privatized and informal ways. The result is a variegated landscape of street vending that is less a function of the rights that the city grants to vendors or the restrictions the city puts on them and more a reflection of the power, influence, resources and resolve of property owners and business improvement districts to exert control over vending and manage public space using techniques of surveillance, intimidation and physical interventions in the streetscape. This article describes how this landscape is produced and lived, while demonstrating the ways in which uncertainty, legal ambiguity and informal practice are intrinsic to the current regime of spatial management in New York.