What is the state of civil society in the Black Sea region? What is the West’s track record in supporting civil society? Why does democracy still remain at the mercy of ruling elites, while donors struggle to create strong citizen pressure for social transformation? This brief focuses on the quality of civil society in Georgia, Moldova, and Ukraine, mostly because they have a more enabling environment for civic activism, a “partly free” system of governance and enjoy substantial investments by the Western donors to develop civil society. The brief addresses general trends and similarities in civil society and points to key missing pieces of the civil society puzzle. It suggests how donors’ approaches to strengthening civil society can be recalibrated to encourage democratization more effectively. Zooming in on these three societies could offer insights about future strategies in the wider Black Sea region.