The limited research on instructors who provide higher education in the correctional environment highlights the complexities of navigating the tensions and restrictions that exist at the intersection of providing quality higher education in the correctional environment. In response to the call to explore how scholars, educators, and activists navigate teaching, including the challenges at the intersection of equity, justice, and education on the ground, the current study considers how instructors navigate the practical constraints associated with teaching in the correctional environment. Through a qualitative investigation of instructor experiences teaching inside correctional facilities across the United States (n = 41), findings support prior research by emphasizing the complexities associated with adapting to and navigating correctional policies related to the provision of credits, degrees, and compensation similar to traditional on-campus course offerings.