Moscow has maintained a constant presence in Africa, dating back to the Soviet era. The USSR, together with its satellite states from the communist bloc, such as Bulgaria, got heavily involved especially in the southern part of the continent, in the context of the Cold War. Moscow forged alliances with African liberation movements fighting against the apartheid regime in South Africa. The anti-apartheid struggle in South Africa finally proved to be successful in 1994, which saw the dissolution of the regime and the election of a new government, although the USSR was by then no longer in existence. Ties between post-Soviet Russia and post-apartheid South Africa continued to develop, reaching a high point with South Africa joining the BRIC group in 2010 founded by Brazil, Russia, India, and China. When Russia started its war of aggression against Ukraine in early 2022, the South African government found itself in a difficult situation. How does South African foreign policy relate to the war is the central question of this article. The answer is not as simple, as the war makes it necessary to revisit the complicated relations between South Africa and Russia in detail in order to understand Tshwane's (Pretoria's) choices. South Africa's motivations and actions remain rather misunderstood by political scientists in Bulgaria. This gap in understanding originates from the lack of research on the topic in the country. The aim of this article is to fill that gap by analyzing and explaining the links between South Africa and Russia, from the anti-apartheid struggle to the present day. In the process, special attention will be given to a number of considerations – including historical, economic, military, domestic, and geopolitical aspects – that are vital for answering the central question. The article will refer to sources primarily in English, Russian, Bulgarian, German, and Afrikaans. In the conclusion the key findings will be summarized and possible future scenarios and challenges facing the South Africa-Russia relations will be presented. This will encompass highlighting, among other things, how South Africa's prioritization of good relations with Moscow might harm its international image.