As most universities move to blended or entirely online digital delivery models, large cohorts of students are excluded from participation. For those universities that espouse the idea that education is democratic, this proves to be problematic. The digital delivery of education, while enabling participation from certain groups such as regional learners or stay-at-home carers, excludes those without ready access to technology or connectivity. Prominent among the latter group are prisoners who in most correctional jurisdictions do not have access to modern technologies or to the internet. This chapter will examine how one university, the University of Southern Queensland, responded to the challenge of delivering digital higher education to prisoners. The journey has been a tortuous one that began with a few idealistic academics acting as champions some three decades ago and became a university-wide project pushing the boundaries of what was technically possible and culturally palatable. The university is now the largest supplier of higher education into prisons in Australia and one of the largest in the world. This chapter will argue that this was enabled by a shift in culture in both the university and in the correctional jurisdictions in which it operates. The university has challenged the largely unspoken but widely held notion that prisoners have limited intellects and are only capable of completing low-level qualifications. The incarcerated learners engaged with the university boast both higher retention rates and better results than their non-incarcerated counterparts.