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For most incarcerated individuals in the United States, communication with loved ones is restricted to costly, heavily surveilled phone calls or brief video visits. Amid these unreliable and profit-driven communication systems, many turn to what prison authorities deem “contraband cell phones.” This paper examines digital access inside US prisons through a digital inequality lens. Drawing on qualitative, in-depth interviews with formerly incarcerated individuals reflecting on their digital experiences during and after incarceration, I argue that prisons represent not just a site of uneven digital access, but of institutionalized digital deprivation. First, I show how first-level digital inequalities are structured by institutional priorities that privilege surveillance and control over connection, failing to account for shifting communication norms in a digital-by-default society. Second, I demonstrate how maintaining access through contraband phones is precarious, risky, and labor-intensive. Finally, I examine how enforced disconnection produces consequences after release, including digital skill gaps that delay educational and employment integration. Attending to the case of digital inequalities in prisons expands scholarship to confront how institutions actively produce and sustain digital deprivation.