Poor postschool outcomes historically await students with disabilities upon graduation. For more than three decades, professionals have responded to this unfortunate reality by focusing on the provision of effective supports and services for the successful transition to adulthood. Social workers play critical roles in supporting this successful transition, yet they are often left out of conversations on policy and practice. One such area involves the role of social workers in the lives of students with disabilities approaching the rights and responsibilities of legal adulthood. Ethics of social work dictate that social workers must navigate a dynamic tension between acting on behalf of “vulnerable” groups and supporting their capacity to act on their own behalf. This tension may create an unnecessary ambiguity when it comes to responding to issues related to adult decision-making support. In this paper, the authors discuss the landscape of decision-making supports in the context of modern social work practice and the ways in which social workers can and should re-think their position on guardianship for transition-age students with disabilities. Practical suggestions to enhance transition outcomes through alternatives to guardianship are provided.