This study examined the experiences of learners who took part in a digital literacy learning program as part of a re-entry program. These learners were provided Internet access for the purpose of acquiring digital skills that would help them transition to the outside world. A digital curriculum that was self-paced and tutor-facilitated provided a structured learning experience for these incarcerated learners. Interviews were conducted with inmates, the program coordinator, and individuals who had gone through the program and were recently released. Qualitative analysis revealed that a peer tutoring model empowered individuals to not only learn the content offered, but also develop socials skills required for persevere in contexts outside the jail.