The purpose of this chapter is to explore urban engagement and participation in the context of smart cities, learning cities, and future cities, focusing on the elements of collaboration, openness, and privacy. As such, a review of the research literature for urban engagement, urban participation, collaboration, and openness and privacy is provided in the context of smart cities. Issues, controversies, and problems are highlighted contributing to formulation of a conceptual framework for urban engagement and participation in smart cities. Using an exploratory case study approach combined with an explanatory correlational design, variables of interest are explored, such as collaborating and privacy, to learn more about the nature of their relationship in contributing to understandings of smart cities. Limitations of this chapter are identified, possibly opening opportunities, challenges, and directions for future research and practice. Insights and ideas emerging from this chapter are presented along with exercises encouraging further explorations.