At a time when higher education in prison (HEP) is growing in popularity and acceptance, a myopic approach threatens the field's potential to develop into a more robust and sustainable enterprise. Blindly accepting HEP as a personal and/or societal good while failing to consider the ethical challenges that individuals engaging in HEP work may face not only does a disservice to those individuals--it does a disservice to the field of HEP as a whole. To that end, the purpose of this critical essay is to shed light on one such challenge in particular: contending with the belief that HEP may somehow help contribute to or legitimate the larger prison system--and therefore, be fundamentally antithetical to the aims of prison abolition. Drawing upon previous interview conversations with faculty who have taught in prison, the author underscores how prevalent this felt tension is among practitioners and thus why it is an area that deserves greater attention. Finally, the author concludes by offering practical recommendations for addressing this issue moving forward.