This study investigates the 2022 decision to outsource parts of the Swedish military pilot training program to Italy, a significant policy shift breaking with over a century of national tradition. Using Carol Bacchi’s WPR approach, the analysis explores the problem representations and underlying assumptions that shaped the decision, as well as what remained unproblematised in the process. The study is based on document analysis and interviews with key personnel within the Swedish Armed Forces. Findings suggest the decision was driven by resource constraints, pragmatism, and gradually normalised assumptions about internationalisation. Pedagogical, cultural, and professional implications were largely marginalised. The study highlights how military policy decisions are shaped by more than operational needs and emphasises the importance of a more strategically reflective decision-making model.