This article documents endeavours to establish a higher education program for incarcerated learners in Aotearoa New Zealand. Presently, prisoners serving lengthy sentences in the country are precluded from obtaining a degree while in custody, which is in stark contrast to other jurisdictions with comparable penal systems. This study examines the challenges of implementing higher education programs in prisons in Aotearoa New Zealand and draws on the authors' experiences to identify potential solutions. Two solutions were considered: a combined universities approach, which involved sharing the costs and efforts of creating a degree program for incarcerated learners among the country's eight universities, and an instance of the Inside-Out Exchange program. However, both of these solutions were impeded by practical and logistical obstacles, including the arrival of the COVID-19 pandemic. Although the initiatives suggested in this study offer promising solutions to these challenges, their implementation has been hindered by practical and logistical difficulties. However, it is argued that it is imperative for policymakers and stakeholders to prioritise the establishment of sustainable and effective higher education programs in prisons, which have the potential to promote social equity and justice. To this end, the authors propose a single university applying for funding to establish and deliver higher education programs in prisons as a practical and viable solution. Policymakers and stakeholders are urged to take action towards realising this proposal, with a view towards creating a more equitable and just society.