School digitalization necessitates effective leadership strategies. How do leaders implement digitalization strategies if they operate in a non-strategic setting? This chapter provides insights into school leadership strategies for sustaining post-pandemic digitalization in rural Indonesia. The schools under study are situated in a “non-strategic setting” due to external and internal factors. Externally, they are in rural areas with limited digital resources, while internally they perceive an incompatibility between their traditional boarding system and digital technology. The findings reveal that while the conventional strategies formulated and applied in schools in developed countries are contextualized, the schools under study have a specific internal constraint that requires a non-conventional internal strategy. This suggests that, despite certain aspects of digitalization being universal and requiring strategies applicable across any organizational context, unique circumstances within organizations can give rise to localized constraints, thus necessitating internalized strategies. Consequently, each school requires both contextualized and internalized digitalization strategies aligned with its unique circumstances. Further scrutiny is warranted for schools with unique conditions considered “non-strategic” (unsupportive of achieving strategic plans) as a new focus area of research in school digitalization or strategic leadership.