This chapter addresses a clearly defined question: how can the ambiguities of the Biden administration’s stance on the Ukraine War be understood? Moving beyond simplistic explanations, this chapter argues that the only way to comprehend the observed pattern is to situate it within the broader context of US-Russia relations since the end of the Cold War. Beginning with a concise overview of the complex situation resulting from the Soviet Union’s collapse and the cyclical nature of diplomatic relations between the two nations, this chapter highlights the unsolvable problem of integrating Russia into the US-led, rules-based international order. Focusing on the long-term consequences of two strategic decisions made by the United States – nuclear supremacy and NATO enlargement – this chapter examines the internationalization of Ukraine’s political crisis and the escalation of the conflict leading to the outbreak of war. Finally, it explores the role of the Ukraine War in the US national security strategy, contrasting the Biden administration’s policies with differing perspectives expressed in public debates on this issue.