During his visit to Ethiopia in 1968, the shah spoke to representatives of the Organisation of African Unity about his commitment to combatting colonialism and racial discrimination. It is surprising, therefore, that not long after the shah had returned to Iran, his diplomats began to discuss with South African diplomats the establishment of political relations between the two countries. The chapter explores the origins of this engagement and examines what drove the two sides together in this period. At the United Nations and other international forums, the shah and his diplomats spoke out in harsh terms against discrimination, racism and human rights violations in Southern Africa. But in spite of this public condemnation, the shah developed and maintained strong security and economic ties with apartheid South Africa. The chapter questions to what extent the shah was able to maintain his position as a champion of independence and human dignity, while enjoying such friendly ties with the apartheid regime.