There has been significant policy interest in Smart Cities as a means of harnessing the power of new IT solutions, urban sensors and Big Data to provide services more efficiently. But Smart Cities are part of a broader set of initiatives with a long history in urban technology and planning to try and generate innovation. Whilst data-driven service delivery initiatives are succeeding on their own, so-called living laboratories, knowledge precincts and other techno-utopian dreams that try to create a holistic Smart City have usually fallen short of expectations. Today's most interesting experiment is Google's Sidewalk Labs Quayside development in Toronto, where the firm is trialing tech solutions to urban problems, including shared mobility. This paper explores what underpins the Toronto experiment, describes what is happening with other Smart City initiatives, and provides critiques of Smart City philosophy from key urban theorists. This is used to explore what it means for innovation in urban mobility, and to identify a set of issues that require resolution.