Abstract: This article investigates relations between Africa and socialist Eastern Europe by tracing the trajectory of the Tanzanian economist Kassim Guruli. It discusses Guruli’s journey in pursuit of higher education from late colonial Tanganyika to Liberia, Guinea, and East Germany. In Tanzania, he was part of a group of Marxist academics from various backgrounds who both supported and challenged official positions on how Tanzania’s experiment in African socialism—ujamaa—should be conducted. In 1977 he was purged from his position, together with other Marxist academics. Negotiating activism, functionary positions, and his relationship with authorities in different national settings, Guruli made use of connections and contacts across various borders; neither ujamaa stalwart nor dissident, his biography does not fit within the narratives of student radicalism or apolitical careerism. Providing a biographical perspective on the transnational dimension of struggles over socialism in Tanzania, and highlighting the important but often precarious position in which returnees from socialist Eastern Europe found themselves, Guruli’s case exemplifies the significance of connections to socialist Eastern Europe forged through educational migration and the role played by Marxist-Leninist actors in postcolonial Tanzania.