This chapter examines educational choices and inequalities therein in terms of the changing nature of educational risk caused by educational expansion. We argue that today adolescents face choices within a much more complex educational system than they did in previous decades. However, because families differ in the extent by which they have the resources required for navigating the risks associated with making these choices, educational inequality may persist in spite of educational expansion. Analyzing class differences in adolescents’ educational expectations for two Danish cohorts born in 1954 and 1995, we find support for the contention that inequalities persist. We discuss the implications of these findings for how educational risks affect the opportunities for promoting social mobility.