The reinstatement of Pell grant eligibility for incarcerated individuals marks a pivotal moment in the landscape of higher education in prison (HEP) programming in the United States. However, despite this promising development, financial barriers persist, hindering the growth and sustainability of HEP initiatives. This qualitative study delves into the challenges faced by faculty, staff, and administrators within Pennsylvania's colleges and universities as they establish and operate HEP programs amidst an evolving funding environment. Drawing on interviews with nine HEP administrators across the state, we explore obstacles they confront, ranging from the Pell grant funding gap to logistical hurdles such as access to educational materials and technology. Moreover, demographic disparities and security concerns emerge as significant factors impacting the relationship between HEP programs and the Pennsylvania Department of Corrections (DOC). Our findings extend beyond financial constraints, revealing broader systemic barriers to equitable and accessible HEP programming. We provide potential policy solutions to address these multifaceted challenges and foster a more supportive institutional environment for post-secondary education in Pennsylvania's carceral system.