This case study investigates the digital literacy acquisition process for learners within a corrections setting. The digital literacy program was part of the reentry program available to some individuals approaching their release date. The case study describes the lab within a prison, and details of how mentor-facilitated, self-paced learning was organized. Examination of the learner path in a corrections setting highlights how learners perceived the relevance of digital literacy in their lives; how they overcame their fears of computers or technology and their self-confidence grew; and potential changes in their self-identity, which often led to imagining new and different possible futures. Implications for these findings include how correctional education and reentry programs can improve post-release employment rates and reduce recidivism by offering incarcerated individuals strength-based skills development training that aim to empower these individuals, foster confidence, capability, and hope for the future.