Objective: States increasingly create promise programs to increase college enrollment and degree attainment. The objective of this study was to understand the experiences of adult learners using the Tennessee Reconnect Grant (TN Reconnect) as they transitioned to becoming college students. Methods: Drawing upon interviews with 23 adult learners, this longitudinal qualitative study applied Schlossberg's Transition Theory to explore the experience of transitioning to college. Results: Findings revealed students who used the TN Reconnect, many of whom were first-generation and low-income students, faced insurmountable barriers that contributed to their decision to initially not enroll in college or drop out of college. Access to TN Reconnect provided an unexpected opportunity for them to return to college. However, participants still faced barriers often associated with adult, first-generation, and low-income students. Contributions: Findings suggest state and institutional policy, and practice must adapt to fit the unique needs of adult learners to maximize degree completion outcomes. As currently structured, promise programs may not provide substantial benefits to student groups who face significant barriers to success, such as adult learners. State policymakers must explore the benefits of adopting a more equitable policy structure and/or implement additional services and resources for adult learners.