This chapter provides an exploration of the notion of urban life, the concept of awareness, and the emergence of the digital, forming an introduction and background to urban life and AI (artificial intelligence) in support of the chapters that follow in this book. As such, a panoramic glimpse of urban life, awareness, and the digital is provided across cities based on the research and practice literature, highlighting key issues, developments, and unexpected events and their aftermath spanning the timeframe of 2010–2024. Challenges and opportunities are identified giving rise to a range of research questions to be explored in this chapter and those that follow. The exploratory methodological approach guiding the inquiry is described along with conference-based polling and interactions that occurred pertaining to key challenges and opportunities for urban life infused with AI. The chapter concludes with the identification of insights, limitations, and future directions.