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Based on a theoretical concept that distinguishes different dilemma types, the article identifies and analyses dilemma situations that arose for the international UN-led peace-building operation in its efforts to combat organised crime in post-war Kosovo. In order to cope with the various dilemmas that arose, the international peace-building operation engaged in compromises that entailed strategic trade-offs. Dilemmas and respective trade-offs in decision-making pertain to the fields of post-conflict security, political inclusion of post-conflict stakeholders, disarmament and demobilization, transfer of ownership, rule of law and local economy.