Limited research exists about transfer of rights conversations between students with intellectual and/or developmental disabilities, their parents, and educators within special education. Through key informant interviews with 14 experts in the field of transition and transfer of rights, the authors sought to understand the factors that influence how such discussions occur. Experts described a set of influential factors. Influential factors included: (1) limited knowledge of school-based professionals about alternatives to guardianship and transfer of rights; (2) that school personnel may have presumptions about student competence; (3) limited student engagement in transition planning and decision making; and (4) the fact that schools are often guided by inadequate district and state policies. The authors offer a set of implications to school administrators that focus on promoting early and ongoing parent and youth engagement in transition planning that emphasizes decision-making awareness and skill building as well as shifting from the outdated paradigm to better align with best practice.