It is well acknowledged that urban populations will increase exponentially. Global bodies like the International Telecommunication Union (ITU) are quite engaged with this issue, articulating the role of information and communication technologies (ICT). However, the basic tenets of such strategies need proactive planning and execution. Proactive planning that leads to sustainable urban areas is an unavoidable challenge for policymakers and planners. It needs systems thinking that argues in favor of a holistic approach by critically analyzing and evaluating past trends, cause-effect relationships, and patterns of exceptions in occurrences, recurrent events, and the way challenges are addressed. Proactive planning also includes present situations and linking behaviors to the past while predicting future behaviors. Such studies are not new in business situations that determine sustainable interventions based on holistic analyses (social, technical, economic, environmental, and ecological dimensions). Proactive planning examples from business argue for preventive actions and being prepared for unknown situations leading to sustainable actions and steady states. Smart cities are no different in this context; any intervention should have sustainable effects with steady states. Smart cities, however, should be looked at in terms of organic growth, and these cities have unique demands on infrastructure, services, and resources. Technologies that transform cities to be smart and sustainable are expected to have all the dimensions of user-centered design and service-oriented architectures. A balanced approach that architecturally aligns cities, society, technology, systems, and governance is necessary, and this is essentially part of systems thinking. In this book, the author takes a holistic approach to explain broad contours of the contemporary topics related to smart and sustainable cities. As the focus is context-aware computing, the book has rightly developed the background so that readers get comprehensive exposure to the related dimensions. The book is based on the concepts of urban design planning, sustainable development, sustainability science, computer science, data science, and ICT. It also touches on various issues related to sociotechnical studies, environmental science, innovation science, policy, ecology, and sociology. Despite its broad coverage of systems thinking, the book also provides scope for further studies by covering aspects of architectural convergence, digital divides, and peri-urban dimensions leading to business-to-business (B2B), business-to-government (B2G), government-to-government (G2G), government-to-citizen (G2C), and citizen-to-citizen (C2C) challenges. A social network analysis (SNA) framework could have helped readers analyze predictable behavior of sustainable and smart growth while managing a cohesive society. More on enterprise integration architecture (EIA) and service-oriented architecture (SOA) would have been helpful. In summary, the book will engage academics, researchers, and students with its broad, comprehensive coverage.