Since gaining independence in 1991, Ukraine has been undergoing a long-winded transformation from authoritarian rule toward democracy. The country’s political orientation has fluctuated between democratization and autocratization, depending on the government in power. As a post-socialist state, Ukraine inherited from the Soviet Union an extensive welfare system, along with a widespread public preference for a strong state role in social protection. At the same time, economic transformation, resource constraints, and demographic shifts have created increasing pressure for social policy reform. Against this backdrop, this chapter examines the extent to which political regime changes have influenced Ukraine’s social policy. Based on an actor-centered analysis, this chapter explores the challenges and driving forces behind these developments, including historical legacies, international reform incentives, and the effects of war. Case studies on the pension and healthcare systems reveal a clear tendency of the Ukrainian state to scale back its social commitments and to realign welfare policy toward financial efficiency and market-oriented principles. However, differences emerge between democratic and autocratic regimes: democratic governments have tended to promote greater transparency and equality within the welfare system.