Medication management is among the most commonly cited reasons for moving to assisted living and is closely associated with resident quality of life. Yet, the issue has received little research attention. Using data from the state-wide study, “Job Satisfaction and Retention of Direct Care Staff in Assisted Living”, this thesis examines medication management practices and accompanying regulations across 45 facilities in Georgia. A combination of quantitative and qualitative analyses is used to examine surveys with 370 direct care workers (DCWs) and in-depth, qualitative interviews with 41 DCWs and 44 administrators. Findings suggest that medication practices are not uniform and vary across settings and frequently, within facilities, in some cases violating regulations. Facility size, administrative philosophy, staff training and backgrounds, resident frailty, communication between staff, and ambiguous regulations, influence medication management. Future improvement will depend on clarifying and modifying existing regulations in ways that are achievable in practice and protect residents’ rights.