In 1976, the United States Supreme Court established an incarcerated person’s constitutional right to healthcare in Estelle v. Gamble. In 2012, in an Arizona District Court, 14 incarcerated persons formed a class alleging the Arizona Department of Corrections was violating this constitutional right. Six years after that initial filing, the Arizona Department of Corrections was held in contempt for violating a settlement agreement it had reached with the plaintiff class. Multiple hearings revealed the deeply systemic—and sometimes fatal—flaws in the monitoring and administration of healthcare in prisons across Arizona. The plaintiff class has continued to struggle to bring the Arizona Department of Corrections into compliance with the settlement, and this has led the court to question the integrity of all monitoring systems and resort to the appointment of an outside expert. This is further complicated by Arizona’s statutory mandate of contracting with private healthcare providers, and the available litigation solutions are increasingly more finite and drastic. This Note explores the Parsons v. Ryan litigation, including possible next steps the court could consider in compelling compliance from the Arizona Department of Corrections; and ultimately suggests the most sustainable solution is systemic change.