Every year, 600,000 formerly incarcerated people return to society, and over forty-four percent will be incarcerated again within a year. As advocates work to improve the conditions of reentry, recent efforts have focused on higher education as the ticket to long-term freedom for formerly incarcerated people. Any success of these efforts hinges on formerly incarcerated people's ability to stay out of jail and to benefit from their participation in higher education. However, despite increases in funding and support programs for formerly incarcerated college students, we know little about their experiences. In this dissertation, I use multiple data sources to investigate the motivations, experiences, and outcomes of formerly incarcerated college students. In chapter two, I show how sponsor organizations like colleges help destigmatize entities like formerly incarcerated people, some potential motivations and risks they face, and I provide common conditions of cumulative destigmatization. In chapter three, I use interview and media data to show how different stakeholders valorize stories of formerly incarcerated college students and how this valorization can serve as both recruitment for prospective students and a source of frustration, especially for students who never live up to their valorization. In chapter four, I use original survey and interview data to show that most formerly incarcerated students have student loan debt, that debt is an accepted reality among them, and that most borrowers either feel "hopeful" or "hopeless" about their debt. In sum, I argue that higher education does not benefit formerly incarcerated people equally, valorizing prominent success stories can backfire, and the debt accrued by some students is vastly disproportionate to their income or expected earnings and can stifle their upward mobility. I conclude by discussing my contributions and some implications from this project and providing future directions for research and policy. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]