This study follows the experiences of adult learners one year after completing a transition program. Transition programs seek to prepare students to enter and succeed in postsecondary education. These programs typically offer remediation and academic skill building and help adult learners to navigate matriculation and financial aid processes. Although there have been some promising studies about the outcomes associated with participation in transition programs, more understanding of how these programs impact adult learners as they seek to enter postsecondary education is needed. There is also a need to better understand how to best support adult learners as they attempt to enroll in postsecondary education. Drawing from the stories of the participants in this study, this article provides recommendations for colleges and universities to better support students in the gap between transition program completion and postsecondary enrollment.