Three case studies provide detailed accounts of digitalization in pioneering smaller medium-sized municipalities. The historical development of digital policy and its governance is reconstructed using process tracing and is divided into phases based on specific configurations of governance. The chapter presents within-case inferences, focusing on long-term continuities and discontinuities in key dimensions of governance, namely actors, scope, organizational distribution, (de)centralization, institutionalization, personnel capacity, and mode of change. The case studies examine explanatory factors influencing transitions between phases of governance, such as political support from the mayor, the presence of digital champions, pilot projects, external grants, and sufficient financial resources.