This article compares the changes in the determination of educational aspirations from the end of the communist period in 1989 to 2003, focusing on a single postcommunist country, the Czech Republic. The Czech case is particularly relevant for comparative research on educational inequality and aspirations, as previous studies have shown that--contrary to one of the main goals of communist ideology--socialism did not equalize access to higher education in the long run. Furthermore, the Czech educational system currently generates more inequality in access to higher education as well as a stronger determination of educational aspirations by social origin than is the case in other Organization for Economic Cooperation and Development (OECD) countries. On the basis of those findings, this article examines whether and how these strong determining forces have changed over time. As background, this article first reviews the literature on the impact of revolutions and other major transitions on educational inequality. The article then contextualizes how the labor market returns of higher education and the continuities and changes in the Czech educational system shaped aspirations during the communist and transition periods. The authors then develop hypotheses about the change in the relationships between socioeconomic background, measured ability, beliefs about the role of education in life success, and educational aspirations from 1989 to 2003. The core of the article is dedicated to presenting the key findings about the role of social background, ability, and the perceived role of education in life success among parents and their children in the formation of educational aspirations of 15-year-old boys and girls. The authors then conclude by summarizing what changes in the determination of the educational aspirations of adolescents have occurred during the 15 years of transition. (Contains 5 figures, 6 tables, and 18 footnotes.)