In 2023, Federal Pell Grant funding was reinstated for learners who are incarcerated, and new regulations were released to govern the eligibility of higher education in prison programs for such funding. This has driven increased interest in higher education in prison programming, as programs look to help their students access Pell grants and adjust their practices to account for the new regulations. At the same time, research and advocacy organizations have also redoubled efforts to better understand how higher education in prison programs are provided, what technology their students have access to, and how the student experience of education in prison differs from the student experience on college campuses. The cultural and institutional focus on security within departments of correction allows correctional institutions wide latitude to practice censorship and surveillance; however, higher education institutions have a duty to protect the privacy and academic freedom of their students. As higher education opportunities expand for individuals who are incarcerated, new configurations and collaborations will be needed to meet these needs. With funding from Ascendium Education Group, Ithaka S+R has published two reports on relevant issues: a report detailing survey findings on technology access in higher education in prison programming and a report on media review directives and censorship policy in higher education in prison. Past work has explored the ways that media review directives and censorship policies may limit or protect student access to intellectual and education material and explored what technology students on the inside can access for educational purposes--and the quality of both the access and use that they have. Building on that work, this report, also made possible with funding from Ascendium Education Group, contributes to the conversation by exploring how educators in higher education in prison programs navigate censorship and self-censorship. Specifically, the authors sought to understand how the institutional context, and the relationship between educational programs and departments of corrections, may have an impact on both how students experience higher education in prison and their learning outcomes.