As a high-priority task in German municipalities, digitalization has attracted significant attention from scholars. However, the majority of research is focused on large municipalities, while some studies focus on digital villages and rural areas. The medium-sized municipality, particularly the smaller medium-sized municipality—a subtype between 20,000 and 50,000 inhabitants—has been mostly ignored by empirical research. Competing perspectives in the literature alternately argue that smaller medium-sized municipalities are in a favorable or unfavorable position for digital transformation based on shorter administrative paths, the purportedly simpler and more agile governance of smaller sizes, economies of scale, and (lacking) capacity. This introductory chapter presents the research design and conceptual foundation required to address this research gap and puzzle. It introduces the questions that guide the study, namely, what characteristics does the governance of digital policy have, which factors influence it, and how does governance influence digital service provision. The chapter explains the mixed-methods design used, introduces key terminology such as digital transformation, digital policy, and governance, and discusses the competing scholarly perspectives on the potentials and limitations of this size.