This chapter examines five successful cases of public sector digitalization in Italy, adopting a bottom-up perspective to understand how feasibility and innovation emerge in diverse operational contexts. The authors analyze P@doc, GIT, the National School Buildings Registry (NSBR), the On-Line Civil Trial (OLCT), and pagoPA, highlighting how each project reflects varied levels of organizational interdependence and technological complexity. These cases are treated as positive outliers that showcase the learning processes and strategic adaptations of local policymakers. The chapter emphasizes that success is tied to the mobilization of local expertise, the blending of technological and organizational competencies, and the ability to create “trading zones” where innovation can be collaboratively developed. It underscores the critical role of policy entrepreneurs at the operational level and the importance of aligning institutional design with implementation realities. Ultimately, the chapter illustrates how policy innovation in digitalization depends on context-aware, experimental, and resilient governance strategies.