Rapid urbanization can result in challenges, such as overcrowding, congestion, and a lack of urban services. To address these challenges, an increasing number of communities are exploring the concept of a smart city (SC). Although rapid urbanization is a problem for cities around the world, its consequences can be severe for those located in developing nations. While previous studies have focused on SCs that were built from the ground up, there is a critical need for studies that focus on how to advance SC initiatives in developing regions faced with limited land and resources. This study identified two proposed SCs in India—Kakinada and Kanpur—which are currently implementing SC projects to explore their SC transformation. This case study aims to explore how “smartness” is understood in these cities and examines the local conditions shaping SC objectives by studying the existing issues in the cities, the proposed projects, and the perception of SC experts on a) what they understand by “smartness”; b) why cities want to become smart; and c) how they will become smart. The study findings indicate that although the high-level goals of the proposed SCs in India are similar to those of existing SCs in developed nations, the underlying objectives and strategies vary and are shaped by the urbanization challenges facing the Indian cities. This research also highlights the key questions a SC planning effort should address, especially in a developing nation context.