Taking as our starting point Levitsky and Way’s analysis of how linkage and leverage have accounted for the success or failure of transitions to democracy in different regions of the world, my colleagues Nino Kemoklidze, Tetiana Malyarenko, and I consider recent developments in Ukraine and Moldova. Both countries have been pulled in different directions—east, towards Russia, and west, towards the EU—as a result of both the linkages that their societies have and the leverage that Moscow and Brussels can exercise. Yet, at the same time, both countries also suffer from systemic crises of institutional weakness and internal divisions that are enabled by competing vectors of linkage and exacerbated by the exercise of great power leverage. Russia and the EU have both tried to pull Ukraine and Moldova into their respective orbits through similar policies: the Eastern Partnership and the Association Agreements with their various promises and the Eurasian (Customs) Union. While Ukraine and Moldova could be simply considered pawns in the larger game of these competing geopolitical projects, our argument is that domestic factors significantly shape eventual outcomes in both countries and in turn influence the strategies and policies of Moscow and Brussels. Based on years of close observation of both countries, including many interviews and focus groups with political leaders and civil society activists in both countries and with Western and to a lesser extent Russian policy makers and analysts, we use process tracing to map trends in trajectories of domestic politics in Ukraine and Moldova in relation to Russian and EU policies over the past decade and analyse the dynamic and co-constitutive relationships between linkage, leverage and institutional weakness to explain patterns of crisis and relative stability in both countries’ protracted transition processes.