The impact of external actors on political change in the European neighbourhood has mostly been examined through the prism of elite empowerment through externally offered incentives. The legitimacy of external policies has received less scrutiny, both with regard to liberal powers promoting democracy and illiberal powers preventing democracy. This article investigates the conflicting notions of legitimate political governance that underpin the contest between the European Union (EU) and Russia in the Eastern neighbourhood. It proposes four mechanisms of external soft influence that take into account the EU’s and Russia’s actorness and the structural power of their norms of political governance, and consider their effects on domestic actors and societal understandings of appropriate forms of political authority. It finally traces the EU’s and Russia’s soft influence on political governance in Ukraine. It maintains that through shaping the domestic understandings of legitimate political authority and reinforcing the domestic political competition, the EU and Russia have both left a durable imprint on Ukraine’s uneven political path.