As part of the infiltration of automation across diverse domains of urban life, autonomous vehicles (AVs), or driverless cars, are traversing cities and regions across the world. This chapter presents a critical analysis of trials of these vehicles, which are being shaped by, and are shaping, the material, political and economic fabric of the city. It takes the burgeoning literature on urban experimentation in a new empirical direction – that of mobility – and deepens understanding of the sense in which such experiments are urban. Its extensive analysis of global experiments with automated vehicles provides an analytical typology of four forms of experimentation – on-road, test bed, precinct and living lab – each with differing relations to the city and differing potentials for political transformation. It illuminates the city as much more than a container for experiments, being multiply implicated in these AV trials through which, we argue, differentiated conditions of possibility emerge for contesting and reconfiguring the city’s ‘automobility.’