This article explores the agency-structure problem in foreign policy analysis of former Soviet Union states, by examining the cases of Ukraine and Armenia. It applies a holistic model of foreign policy analysis that considers its structural, dispositional, and intentional dimensions and outlines a more dynamic structure- agency interplay. While the ideational incentives have been the core rationale behind Ukraine’s and Armenia’s drive towards Europe, the structural constraints, along with arbitrary decisions of the authoritarian incumbents would considerably obstruct countries’ rapprochement with Europe. Thus, as the article concludes, along with structural constraints, stemming from Russian resistance to Europeanization, agency-level factors, such as the preferences and perceptions of Armenian and Ukrainian presidents have been critical to shaping countries’ foreign policy outputs.