Facing massive protests, why did incumbent regimes in both South Korea and Poland repress movements for democratization in the early 1980s but make democratic concessions to the opposition in the late 1980s? I demonstrate how the United States and the Soviet Union as superpower patron states influenced democratic transitions in South Korea and Poland. The different outcomes across time are partially attributed to superpower policies toward their client states. Absent in 1980 were strong, credible signals from the United States and the Soviet Union to their respective client states to support political liberalization. But in the late 1980s superpowers affected the calculus of client state elites by either signaling or encouraging governments to make concessions to the opposition.