The Russian-Ukrainian conflict has heightened security concerns in the Black Sea region, particularly for Romania, Bulgaria, and Moldova. This article examines how historical-cultural legacies in the Eastern Balkans – political-historical, territorial, ideological, religious, and ethno-linguistic – have shaped enduring Russophile or Russophobe sentiments, influencing each country’s response to the war. Although all three governments condemned Russia’s aggression and expressed support for Ukraine, their practical measures diverged. Romania adopted a full-fledged balancing strategy, combining sanctions, military support, and increased defence spending. Bulgaria pursued a lukewarm balancing posture, endorsing sanctions but avoiding substantial military commitments. Moldova engaged in façade balancing, issuing condemnations without imposing sanctions or enhancing defence capabilities. The article argues that these differences stem less from membership in Euro-Atlantic institutions than from the depth and direction of legacy-based attitudes toward Russia, which continue to shape official discourse, economic decisions, security policy, and public opinion across the Eastern Balkans.