This chapter synthesizes the qualitative and quantitative findings of an exploratory sequential mixed-methods study to address the challenges of digitalization capacity in smaller medium-sized municipalities. It highlights the characteristics of digital policy governance, the factors influencing it, and the relationship between governance and digital service provision. The quantitative findings reveal that most smaller medium-sized municipalities face significant challenges with digitalization. Nearly two-thirds of these municipalities have weak institutions for governing digital policy, and almost half exhibit a medium-low availability of online services. However, there are also pioneering municipalities with well-developed digitalization governance and a broad range of online services. A positive correlation between certain institutionalized organizational structures and online service provision underscores importance of governance in advancing digitalization. The case studies demonstrate that pioneering municipalities follow a trajectory of growth and institutionalization in the digital policy field over time, with case-specific variations in organizational structures, (de)centralization, and modes of change. The interaction of explanatory factors—such as political support from the mayor, digital champions, pilot projects, external grants, changes to the legal framework, and the municipality’s financial situation—creates a positive feedback loop that fosters growth trajectories. The conclusion highlights the limitations associated with municipal size in relation to digitalization while also recognizing the existence of pioneering municipalities. It advocates for a nuanced perspective on the factors that interact with size to either promote or constrain digitalization. The chapter proposes avenues for further research on change agents, the role of mayors, and policy diffusion, and it discusses practical implications and policy recommendations.