This paper explores a proposal for an off-line e-learning platform that will provide a bridge for digitally unconnected students and educators to join the contemporary information and communications technology (ICT) intensive world. Individual remote and unconnected learners face a chicken and egg problem for engagement with contemporary e-learning offerings. Without connectivity, remote learners have no way of engaging with now common ICT intensified learning materials that are intended to teach them how to engage in an ICT intensive world! The paper takes systems approach to developing a solution that will fit into the world we have, and not one we wish we had in terms of infrastructure, economics and skills available in remote and developing regions. Digital learning courses are placed onto a portable e-learning environment that is not reliant on a constant network connection to function but retains interactivity, analytics and the ability to synchronise data with an educational institution when a connection is found.