Objectives. To understand point-of-care decisions, and in particular rule breaking, by personal support workers (PSWs) regarding institutionalized elders with dementia within a context of legislative and organizational care mandates. Methods. Qualitative baseline data including focus groups and semi-structured interviews with PSWs (n = 26) and supervisors (n = 9) were collected during a 2-year, multi-method trial of a 12-week interprofessional arts-informed educational intervention in two Alzheimer support units and were analyzed using a critical realist approach. Results. PSW care decisions were the outcome of a discordant interrelationship between PSWs’ reflective deliberations, and legislative and organizational care mandates. PSWs responded to discordance through rule breaking in order to provide individualized care. Unbeknownst to PSWs, rule breaking was contingent upon supervisors’ case-by-case complicity as they strove to balance fears of regulatory citations with private assessment of the soundness of PSW logic. Discussion. Quality care emerges at the intersection of policies governing long-term care, PSW rule breaking, and the supportive but undisclosed role supervisors play in these violations. Understanding this complexity has important implications for initiatives to improve care practices and to challenge legislation and policies that impede dementia care.