Although higher education has been linked to better income, longer life expectancy, and better health, about 25–45% of incoming college freshmen never graduate. The current study examined whether optimistic expectancies are associated with college retention. Participants (N = 2,189) were given surveys when entering college, and academic records were attained after freshman year completion. Dispositional and academic optimism were associated with less chance of dropping out of college, as well as better motivation and adjustment. Academic optimism was also associated with higher grade point average (GPA). Structural equation models revealed that dispositional optimism predicted retention through motivation and adjustment, which in turn predicted retention. Academic optimism, on the other hand, predicted retention through its effect on GPA, motivation, and adjustment.