In the interstices of Cold War rivalries and anti-colonial agitation in late 1950s Africa, African workers came into the focus of African nationalist politicians, Western leftists, colonial regimes and state socialist states alike. They were a small, but influential group, increasingly organized in trade unions and capable of bringing whole economies to a halt. European communists on both sides of the Iron Curtain saw these workers not only as part of an inceptive working class but also debated their role as a potential key force in global anti-capitalist revolution – if they had the right concepts. But how could trade union representatives, particularly those ones from Eastern Europe, actually get in touch with their African counterparts? Based on archival materials of the East German Freier Deutscher Gewerkschaftsbund (FDGB), this article discusses East-West-South connections in labor education with a special emphasis on the role of Western trade union officials working for or affiliated to the communist-dominated World Federation of Trade Unions (WFTU). Drawing on their international experience, personal networks and linguistic skills, French and British communists established and intensified links between African trade unions and WFTU affiliates like the FDGB in the 1950s and early 1960s. Their influence facilitated and shaped these East-South connections. First, through their networks in West Africa, Western communists enabled the WFTU and the FDGB to internationalize their concepts of trade union education and integrate it into African political structures. Secondly, we examine the African Workers’ University in Conakry, an East-West-South joint venture between the West African Union Générale des Travailleurs d'Afrique Noire (UGTAN) and the WFTU, where trade unionists from the entire African continent attended courses between 1960 and 1965 and where European communists broadened their horizons while often holding on to rigid views. Thirdly, the article examines how European trade union functionaries talked about African course participants behind closed doors—building on the transcripts from a 1963 WFTU gathering on education for African trade unionists. Emphasizing their insider knowledge, French communists with experience in African trade union education called for innovative pedagogical concepts including a more practice-related education which acknowledged the heterogeneous conditions in different countries. However, they also promoted Eurocentric stage theories and saw a need to “discipline” Africans. The article concludes that the cooperation between actors from East, West and South rested on some shared assumptions, but encounters also led to reconceptualizations and realizations of ideological and practical constraints in international labor education.