Smart city development is recognized as a potential solution to urbanization issues. This study examines Philippine cities’ readiness for smart city development by answering three policy questions: (1) What drives Philippine local government units toward implementing smart city initiatives; (2) What is the extent of smart city development among Philippine cities; and (3) How can the Philippine government facilitate the development of smart cities? A desk review of smart city initiatives in some Philippine cities was carried out, and interviews were conducted with local government units, national government agencies, businesses, and development organizations. It finds that the Philippines has started to tread the path toward building smart cities, and some cities already exhibit readiness. However, additional pathways to smart city development must be paved. There is a need to address funding, data management, and sustainability challenges. Addressing the challenges not only requires actions at the local level but also demands additional support from the national government in developing policies and standards to improve data flow, promoting technology- and innovation-powered cities, and ensuring transparency and accountability in the implementation of smart city initiatives.