This paper presents findings from a study of the experiences and outcomes of older and younger community college students. We developed a discrete-time hazard model using longitudinal transcript data on a cohort of first-time community college students in Florida to compare the impact of enrollment pathways (such as remediation) and enrollment milestones (such as attaining a certain number of credits) on educational outcomes of older students—those who enter college for the first time at age 25 or later—with those of traditional-age students. Results suggest that reaching milestones such as obtaining 20 credits or completing 50 percent of a program is a more important positive factor affecting graduation probabilities for younger students than it is for older students. We also found that although enrollment in remedial courses decreases the odds of graduating for all students, older students who enroll in remediation are less negatively affected than are younger ones who take remedial classes.