This exploratory, descriptive study examined trends associated with Kalamazoo Promise (KPromise) student stop out, reenrollment, and persistence to a credential upon reenrollment. For the 2006–2017 cohorts, 78% were retained from first to second year. Inferential models suggested that first-year stop out was mainly correlated to students’ high school free-and-reduced lunch eligibility (FRL) and high-school GPA. Forty-five percent of stopped out students reenrolled, and reenrollment was primarily correlated with time. The median time to return was 3 non-summer semesters, with Black/African American and Hispanic/Latino(a) students predicted to reenroll in fewer semesters than White students. For the 2006–2012 cohorts, 30% of all stopped out students who reenrolled have earned a degree to date. Upon reenrollment, nearly half of all postsecondary certifications were earned by FRL students. Discussion links our findings to wider trends, highlights actions to bolster outcomes, and illustrates how this study could be a benchmark comparison for other tuition-free policies.