In this paper, we examine the antecedents and consequences of timing in the transition from high school to college. Using the National Education Longitudinal Study of 1988 (NELS:88), we find that 16 percent of high school graduates postpone enrollment by seven months or more after completing high school. Delayers tend to have some common characteristics: they come from families with few socioeconomic resources, they have performed poorly on standardized tests, they have dropped out of school, and they have exited high school with a GED. We find that even after controlling for these academic and socioeconomic characteristics, students who delay postsecondary enrollment have lower odds of bachelor degree completion. Additionally, we find that delayers are more likely than on-time enrollees to attend less than four-year institutions and to transition to other roles such as spouses or parents before entering college. Controlling for institutional context and life course contingencies, however, does not completely explain the negative relationship between delayed enrollment and degree completion. The following is appended: Covariate Construction and Classification. (Contains 5 tables.)