Automated driving has attracted intense attention in the media and among the general public, based on extremely optimistic predictions from some industry participants, but these have started to become more realistic in the last couple of years, after the “hype cycle” for automation peaked. This paper explains the opportunities for Automated Driving System (ADS) technology to improve the urban transport of people and goods, together with the challenges that will limit the scope and timing of the deployment of urban ADS. The discussion emphasizes the diversity of ADS applications and services, each of which has its own opportunities, challenges, and uncertainties, leading to diverse deployment scopes and schedules. The associated challenges are sufficiently daunting that ADS deployment will lag behind electrification and connectivity, leaving more time for cities to prepare for it.