At the NASFAA convening Breaking Barriers: Bridging Worlds in Prison Education and Student Advising convening in June 2024, the National Association for College Admission Counseling (NACAC) led a panel discussion exploring questions and practices in recruiting and admissions in higher education programs for students who are incarcerated. This webinar continues that conversation. People who are incarcerated have limited access and agency when trying to learn about options and make responsible decisions about their educational pathways. Often, correctional system policies create restrictive barriers and define limits for recruitment and admissions that need to be considered. Colleges and universities doing prison education have to find compromises that accommodate environmental constraints while still ensuring compliance with institutional policies.