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Reducing incarceration and confinement is a persistent and divisive national problem. Education is often touted as both the problem and the solution to this societal issue. Researchers note that low academic achievement is linked to higher rates of recidivism and that people who have been incarcerated tend to struggle in academic and vocational settings. The author examines what participation in a digital literacy acquisition program looks like for learners moving through the reentry process. Data are part of a larger mixed methods study involving over 12,000 learners, 500 tutors and 100 semi-structured interviews with learners, tutors, and key stakeholders. Interviews were analyzed using grounded theory and themes were iteratively developed by six members of a research team. The reentry setting was what we came to see as a telling case that provided unique insights into what the digital literacy acquisition process looked like for soon to be released learners. Analysis indicated that the digital literacy acquisition process, as part of a larger holistic approach to reentry, created a new figured world which supported the development of new identities in practice, which in turn allowed the participants to develop new imagined futures.