This article reports on the preliminary findings, design criteria and lessons learned while developing and piloting an alternative to traditional print-based education delivery within a prison environment. PLEIADES (Portable Learning Environments for Incarcerated Distance Education Students), was designed to provide incarcerated students with access to internet-independent secure digital and mobile technologies. An internet-independent version of Moodle was developed to complement course readings deployed on eReaders. The aim of the project was to increase access to and participation in higher education courses that are increasingly offered exclusively online. The article begins with an overview of the current provision of education within prison environments and introduces the rationale for commencing the project. The research findings of the project trial are discussed and the paper concludes with the lessons learned and implications for further research, development and implementation.