This chapter reconstructs the events that Yugoslav diplomacy encountered in two distinct historical contexts: the Balkan Federation project, elaborated during WWII, and the collaborative defense and political agenda coordinated with Greece and Turkey under the Balkan Pact negotiations from 1950 to 1955. Typically, the Balkan and international historiographies have treated these events in isolation, with the Yugoslav expulsion from Cominform in 1948 marking a powerful ideological divide in the communist geopolitical landscape of the Balkans. Moreover, the Balkan Pact has been mainly examined by prioritizing its military and defense components. However, investigations into Yugoslav and Italian archives uncover a surprising continuity between these two historical contexts. Notably, the attitudes and actions of key regional and international players greatly influenced regional developments despite the differing ideological positions and historical legacies resulting from Tito’s partisan triumph, the Greek civil war, the Cominform breakup, and the NATO efforts to engage with the Balkans through Belgrade, all of which faced resistance from Italy. Therefore, while the concept of “historical continuity” always requires a scholarly cautious approach, the events scrutinized in this chapter reveal an intriguing connection to enduring federal (or confederal) projects in the Balkan political discourse since the early nineteenth century.