The problems associated with undue and overbroad guardianship for people with intellectual and developmental disability (IDD) have received increasing attention in recent years. In simple terms, guardianship threatens one's ability to exercise self-determination and make important decisions that reflect their own unique values, preferences, and goals. As such, there is both a practical and ethical argument for special education professionals supporting youth with IDD and their families in navigating the transition to legal adulthood using the least restrictive means possible for adult decision-making support. The current study explored responses to an open-ended item from two surveys with special education leaders (n=117) and special education teachers (n=272) on what they perceived to be the most challenging aspects of supporting students and their families to this end. Between these two groups of professionals, 328 responses were collected. Findings from a thematic analysis yielded a total of four themes represented by these responses: (1) lack of professional training, knowledge, or resources; (2) lack of family training, knowledge, or resources; (3) not applicable to teacher population or setting; and (4) infrequent family involvement or low expectations. Each theme is presented alongside illustrative quotes and followed by a discussion of the implications of these challenges for the field and directions for future research.