What do recent trends toward increasingly ambitious educational expectations and rising college completion rates mean for the stratification of higher education? This article shows that the odds of achieving expectations for a bachelor's degree increased across 15 cohorts of young adults, and to a lesser extent, for expectations to attend graduate/professional school. Gender-related constraints on realizing expectations for a bachelor's degree weakened, while constraints associated with minority racial/ethnic and lower socioeconomic statuses did not. Recent trends in educational stratification were thus a mixture of fulfilled expectations for growing proportions of some young adults, but continued social constraints for many others. Note, these results are derived from the experiences of high school seniors successfully reinterviewed over time, who are advantaged relative to school dropouts and nonrespondents. [An earlier version of this article was presented at the 2009 annual meeting of the Southern Sociological Society, New Orleans, LA.)