This chapter provides a comprehensive account of the US-Baltic alliance formation stage. Drawing upon sizable archival material and interviews with key participants, the following delves into the complex dynamics of the Baltic road to NATO. From today’s vantage point, it may seem like a foregone conclusion that Estonia, Latvia, and Lithuania were somehow destined to join the transatlantic alliance. The material presented, however, starkly illustrates that this was never a preordained outcome. Before the turn of the century, the idea that NATO would extend Article 5 responsibilities to small states in the backyard of a nuclear-armed Russia seemed highly unlikely. Given Russian objections and the overwhelming consensus across European capitals against eastward expansion, how did Riga, Tallinn, and Vilnius defy the odds and squeeze under the NATO umbrella? By interrogating a vast trove of US and Baltic sources, the following peels back the various layers of this process and breaks new ground in the NATO expansion literature.