This article discusses the digital inequalities experienced by prisoners and the potential opportunities that providing ‘new’ media in prisons offer for offender rehabilitation and resettlement. Currently denied access to online and social media that most of us take for granted, and unable to communicate in ways that have become ‘ordinary’ in the wider community, it is argued that prisoners experience profound social isolation and constitute one of the most impoverished groups in the digital age. In prisons which provide selected prisoners some access to information and communication technologies, their high socio-cultural status and consequent construction as a ‘privilege’ frequently results in them being used in the exercise of ‘soft’ power by prison officer gatekeepers. Moreover, when prisoners come to the end of their sentences, they not only are faced with prejudice and poor job prospects due to their criminal record, but their digital exclusion during a period of incarceration may have compound effects and lead to long-term and deep social exclusion.