This article analyses the history of Assicurazioni Generali in Turkey and Romania from the nineteenth to the twentieth century, focusing on how a major European insurer adapted to imperial collapse, nation-state formation and regime change. In the Ottoman Empire and later Turkey, Generali expanded through agency networks, local affiliates and real estate investments. In Romania, it consolidated its position through Generala, which became one of the country’s leading insurance firms in the interwar period. The article also examines the effects of authoritarianism, war and communism, showing the contrasting post-war outcomes of nationalisation in Romania and continuity in Turkey. It argues that Generali’s long-term resilience depended on its capacity to reorganise transnational networks within changing political environments.