What shapes a country’s foreign policy formation in times of crisis? This article explores the factors that were behind the response of Ukrainian decision makers in their relations with Russia and the European Union during the annexation of Crimea between February 21 and March 26, 2014. I view Ukraine’s foreign policy through the lenses of an analytical framework inspired by game theory, where the decision-making process is divided into four parts—information about others’ preferences, trust in interlocutors, everyone’s payoffs, and resources. This article employs a rigorous qualitative thematic analysis of 38 elite interviews, numerous primary documents, and media reports. The core finding suggests that the uncertain times and unpreparedness of Ukrainian decision makers obstructed them from a comprehensive analysis of the environment and formation of the country’s foreign policy strategy, which, consequently, facilitated Russia’s annexation of Crimea.