This paper reports on a project that was first introduced to World Conference on Mobile and Contextual Learning attendees in 2012, the PLEIADES project (Portable Learning Environments for Incarcerated Adult Distance Education Students) and discusses how this project evolved into two separate projects; one each from the two technologies originally trialled. PLEIADES introduced a version of an internet-independent version of the Learning Management System (LMS) called Stand Alone Moodle (SAM) and eBook readers to incarcerated students in a correctional centre in Southern Queensland. The Triple ‘E’ Project (Empowerment, E-Learning and E-Readers) using eBook readers similar to those trialled in the PLEIADES project, were rolled out to a further four correctional centres. This paper explores the issues and challenges involved with deploying eBook readers to incarcerated students through the PLEIADES and Triple ‘E’ projects.