Since World War II, value liberalization has been a worldwide trend, but more recently, there has been a resurgence of conservativism. Modernization and cultural theories have difficulty explaining the shift to liberal or illiberal values, but the political environment, an underestimated contextual factor, could shed light on the mechanisms driving it. This study used hierarchical linear modeling on all six waves of the World Values Survey data (1981–2014) to demonstrate that political freedom helps to explain the rise and fall of liberal attitudes when controlling for societal affluence, inequality, and cultural backgrounds. It finds that political freedom conditions the effects of education: although education is usually considered a liberalizing force, its effect is much weaker in non-free than free societies. The findings remind us of the importance of a free political environment for a robust democracy and point to the complex nature of educational effects, namely the ability of education to socialize people in liberal or illiberal directions depending on the political context and the regime’s agenda.