Using 1,400 survey responses collected from two large urban community college systems in Texas, this study examined how students' financial habits, stress, and well-being influenced their enrollment behaviors. Working students, compared to their nonworking peers, reported significantly lower levels of overall financial well-being. After controlling for other relevant predictors of persistence, regression results showed that students with lower financial well-being and higher financial stress were more likely to doubt their ability to complete college. Results for the restricted sample of working students revealed a strong relationship between a student's financial well-being and stress. These students also reported having to reduce their semester course load and/or stopping out for a semester in order to work more hours to pay for expenses. These findings suggest that initiatives aimed at helping students improve their financial literacy and money management skills may be an effective, yet underutilized, way to improve retention rates at community colleges.