Abstract: The juvenile justice system is predicated on a theory of rehabilitation with concern for protecting juveniles and society. For lesbian, gay, bisexual, and transgender (“LGBT”) youth, however, the system has developed into a punitive arrangement. LGBT youth face higher rates of criminalization and incarceration for non-violent crimes than any other group of youth. They also face unique threats, including sexual, physical, and emotional harassment; isolation; and a lack of medical care. Transgender youth are especially impacted. In response, victims have increasingly brought constitutional claims against federal prison officials for unconstitutional conditions of confinement. The courts are inconsistent on whether the judiciary should utilize the protections of the Fourteenth Amendment’s due process clause or the Eighth Amendment’s proscription against cruel and unusual punishment to evaluate juvenile conditions of confinement cases. This Note weighs the two approaches to determine that the due process clause is more protective of transgender and LGBT juveniles more broadly.