This chapter offers readers an opportunity to reflect critically on the new frontiers of digitization in relation to prisons. Our collective research and scholarship has led us to reflect poignantly on the impact and consequences of digitization and explore more closely the ethical factors of this evolving landscape. Prisons are experiencing a digital revolution and this is a poignant moment in the history of the modern prison. Elsewhere we have made recommendations for meaningful and responsible digital implementation to prisons and consequently we began to explore the ethical dimensions of this practice. In our chapter we outline the key moral drivers in respect to the digital prison. We apply suggested models of digital rehabilitation and disruptive innovations proposed by other scholars and suggest the fundamental ethical principles that would sensitively respond to the prison setting and its people. Our theoretical development has global potential for digital developers, prison practitioners, policy makers as well as prisoners and provides a significant contribution to the evolution of digital criminology and computer ethics.