This Article argues judicially-imposed rigid rules governing the conduct of those responsible for providing adequate healthcare to the incarcerated will not reform prison healthcare. This is largely because the “need to customize and adapt makes rules an ineffective means of controlling discretion.” Instead, judges and policymakers should supplant limited rules with principles of ongoing monitoring and correction of these facilities if they hope to improve these facilities’ provision ofhealthcare. Part I quickly describes the United States’ criminal legal system and the dire conditions inside American prisons, jails, and detention centers. Part II surveys class-action litigation challenging inhumane healthcare provisions in four jurisdictions, each one using a different healthcare delivery model. Part III examines how institutional systems and structures at these facilities may be improved by incorporating systems of ongoing monitoring and correction, in line with the principles used in the Alabama-Utah model of child welfare service provision. Finally, Part IV offers a brief conclusion and notes possible implications for correctional facilities across the country.