This paper explores an Australian trial of mobile learning technologies, including internet-independent eBook readers loaded with tertiary preparation materials, which attempted to improve access to tertiary courses and pathways for incarcerated students. Attempts to close the digital gap for incarcerated students however reveal deeper and persistent problems within the digitized and vocationalized university, economy, and society. While delivering economic efficiencies and flexibility for some, the digital revolution may also be reducing opportunities for the most marginalized of students such as incarcerated students and other groups without direct internet access. Education technology interventions which aim to prepare incarcerated students for the digital knowledge economy must also consider the situated context of the postmodern prison and the social, political and cultural practices and problems that emerge around the technology. In the face of neoliberal undercurrents fueling the vocationalization of prison education it is particularly necessary to recognize the inherent personal and social value of a humanities education. The challenge is to ensure incarcerated students are not left behind in this digital age and to balance institutional prison priorities such as order and security against opportunities for authentic and current learning experiences within the Humanities.