A diffused assumption within the Italian foreign affairs community argues that the relationship between Italy and Russia follows a generally cooperative attitude, fostered by strong cultural, economic and political ties. This narrative misses a significant part of the tale, which is at odds with the idea that the good offices with Moscow represent a ‘constant feature’ of Rome’s foreign policy. Indeed, a competitive interaction has frequently emerged, as a number of events in the last decade confirm. To address this shortcoming, the article aims at providing a more nuanced interpretation of the investigated relationship. Focusing on the outcomes of structural changes on Italian foreign policy, it posits that Rome is more prone to a cooperative stance towards Moscow whenever the international order proves stable. By contrast, its interests gradually diverge from those of its alleged ‘natural’ partner as the international order becomes increasingly unstable. This hypothesis is tested by an in-depth analysis of Italy’s posture towards Russia amidst the crisis of the international liberal order (2008-on). Furthermore, the recurrence of a similar dynamic is verified through a diachronic comparison with two other international orders in crisis, i.e. that of the interwar period (1936-1941) and that of the Cold War (1979-1985).