This study explored key aspects of resident transitions to assisted living (AL), including the frequency and importance of preadmission resident education and the potential role of social workers in this setting. To examine the factors that may help or hinder resident transitions to AL, a written survey was administered to a statewide, geographically representative purposive sample of Medicaid Assisted Living Waiver providers (N = 28). Findings suggest a positive relationship between the availability of a social worker and the frequency and importance of resident preadmission education in several areas. Results also suggest a gap between what AL providers believe is important for resident transitions and what is actually happening in their facilities. Social workers may play a significant role in providing preadmission education and are well positioned to address the unmet psychosocial needs of residents and family members during the transition to AL. Future studies should specifically examine the contributing role of social workers during the period of adjustment to AL and the effect of social work services on the well-being of AL residents and families in AL settings.