This chapter outlines the research design guiding the empirical inquiry into digital transformation in Italy’s public sector. The authors justify Italy as a least likely yet instructive case to study public sector digitalization, due to its complex political context, fragmented governance, and limited prior success in reform. The empirical strategy emphasizes positive deviant cases—instances where digitalization achieved operational success despite institutional inertia. The chapter details the selection of both national and sub-national cases to capture variation in technological and organizational contexts. It also explains the methodology, which includes document analysis, qualitative interviews, and longitudinal tracking of policy implementation. Interviews focused on actor roles, innovation dynamics, resistance, and adaptation strategies. The approach emphasizes learning from within-case variation and process tracing to identify mechanisms behind success. The chapter sets the foundation for analyzing how theoretical frameworks on digital governance and Digital Service Teams (DSTs) apply in practice, highlighting the relevance of adaptive strategies and contextual awareness.