A post-secondary qualification earned in prison has been noted as a factor in reducing rates of recidivism and contributing to improved prisoner behaviour. However, delivering higher education into prisons is a challenging process. In Australia, many higher education institutions prioritise online modes of delivery, and most jurisdictions prohibit prisoner access to the Internet. The lack of Internet access means that incarcerated students do not have the opportunity to experience learning in the same way as students who are not in prison. Digital technologies, including mobile devices, offer affordances in terms of providing the incarcerated student with a digital learning experience. From 2012 to 2017, a university research team in Australia has been trialling digital learning initiatives in 28 prisons across the country. The Making the Connection project aims to enhance the student learning experience using an offline learning management system and personal devices. Even so, introducing digital technology into prisons is a challenging process. Prisons have low levels of trust and strict security requirements. Digital technology must comply with jurisdictional constraints and correctional centre policies. Personal devices must be ‘prison-suitable’ yet at the same time ‘user-friendly’ for incarcerated students who traditionally do not have high levels of literacy, including digital literacy. Providing prisoners with mobile devices requires trust in two dimensions: researchers trust the prisoners to use and maintain the devices for learning purposes, and prisoners trust the researchers to provide a pedagogically-appropriate learning tool. This paper reports on the complex process of preparing and deploying mobile technologies in Australian correctional centres.