This article uses the lens of education to elucidate multidimensional transformations affecting gender equity in the process of democratization in CEE, SEE, and FSU countries. First, the article suggests that postsocialist transformations in these areas have not automatically resulted in greater gender equity across the region but rather have led to a variety of gender outcomes in particular geographic, economic, and historical contexts. Second, the article proposes that transformation processes in the former socialist block have had differential effects on gender equity in education, negatively affecting both female and male students depending on contextual variables.