We analyse trends in female inclusion in secondary education in a large set of (post-)socialist countries in a regression discontinuity design (RDD) as well as include non-socialist countries as contrasting cases in multilevel analyses. We test under which conditions the implementation of socialism increased the participation of women in secondary education and, at the same time, whether the post-socialist transformation after 1990 decelerated or even reversed the trend towards women’s inclusion in (secondary) education. In the second step, we aggregate individual indicators of values and culture related to secularisation and emancipation to the country-year level and apply latent class analysis (LCA) to assign each country-year to a respective cultural sphere. We investigate how these cultural spheres, as well as a country’s status as a socialist country, moderate the effect of female participation in secondary education. We also test how cultural spheres and socialism moderate the risk of achieving only lower education for women while controlling for indicators of economic development and individual-level characteristics. Overall, socialism reduced the risk of receiving only a low education, but this effect was significantly weaker for women than for men.