After the Cold War, Italy started to act as an international peacekeeper, deploying troops in dozens of military operations, mainly within multilateral frameworks. Recently, with the end of the “war on terror” and after the 2015 White Paper, Italy devoted growing interest and resources to the “Enlarged Mediterranean”. Despite Italy’s post-bipolar military dynamism, limited attention has been paid to assessing missions. The withdrawal from Afghanistan, as well as the debate about European Union defence and NATO, particularly after the Russian aggression on Ukraine, have emphasised again the need for a detailed analysis of Italian operations. This analysis discusses the effectiveness of international interventions and the features and the trajectory of Italian missions. Three policy recommendations are advanced: the need to 1) create standard and systematic evaluations as events proceed; 2) establish transparent and inclusive assessments when interventions are completed; and 3) plan strategically for long-term proactivity rather than short-term reactivity.