The benefits of postsecondary degrees are striking for populations who have experienced incarceration, yet little is understood about how this population succeeds with educational attainment upon release from incarceration. This qualitative collective case study examined to what extent and how six formerly incarcerated individuals who started educational programming while incarcerated successfully persisted with postsecondary degrees after being released back into Maine communities. This study found that participants related education to self-care or treatment, described their own education journeys as different, or taking a different path, and felt motivated to persist with education despite external expectations, which one participant labeled "transformational resentment." All participants also identified a need for more individualized reentry supports to help formerly incarcerated students persist with education. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]