This thesis analyses the making of West German policy towards the Portuguese dictatorship during the governments led by Willy Brandt and Marcelo Caetano, from 1968 until the dictatorship's downfall on 25 April 1974. This case study sheds new light on the interaction between the Cold War and colonial politics, particularly on the multilateral dimension of the process of Portuguese resistance to decolonisation. Although the starting point is the bilateral relationship between the Federal Republic of Germany and Portugal, this thesis takes a multifaceted approach to the topic. It examines the role of various external and internal forces pushing for change and continuity in Bonn's policy towards Lisbon. Research demonstrates that not only did that policy become a contentious issue internationally, it also polarised West Germany's society, parliament and different sections of Bonn's social-liberal coalition government. Taking this into account, my work covers the diplomatic, economic and military areas of the relations between the two states. It also addresses the parallel ties between the German Social-Democratic Party and the opposition to the dictatorship, including the Portuguese socialists and the African liberation movements. The thesis argues that, despite many impulses and pressures to assertively confront the Portuguese dictatorship's refusal to decolonise and democratise, West German policy towards the Caetano regime remained essentially cooperative, even if becoming increasingly ambiguous over time. That option reflected the geopolitical and conceptual contradictions between adopting a more aggressive policy towards Portugal and defending Bonn's contemporary policy of rapprochement with Eastern Europe (neue Ostpolitik). Thus this thesis illustrates the interconnectedness between the global Cold War framework and the perpetuation of colonialism in Africa.