Understanding the elements of educational success for adult English language learners (ELLs) is an important priority for correctional educators, especially today with an increased population of non-English speaking students in correctional schools throughout the country. There is a dearth of information, however, about incarcerated adult ELLs and how they approach learning in an academic context. This article documents the five-year journey of Adalberto, an 18-year-old incarcerated Hispanic student in Maryland and his quest for a General Educational Development (GED) diploma. Challenges included similar situations found in a more traditional high school and also unique situations found only in correctional education. Factors influencing Adalberto's educational success included reading extensively in his second language, using bilingual dictionaries and textbooks, articulating his goals in class, cooperative learning including the use of inmate tutors, and being a positive role model for other ESL students.