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The Eighth Amendment has long served as the traditional legal vehicle for challenging prison conditions, including long-term isolation or "supermax" confinement. As described by Hafemeister and George in their article, The Ninth Circle of Hell: An Eighth Amendment Analysis of Imposing Prolonged Supermax Solitary Confinement on Inmates with a Mental Illness, some prisoners with mental illness have prevailed in Eighth Amendment challenges to prolonged isolation. Yet an equal or greater number of these claims have been unsuccessful. This Essay considers why some of these cases fail, and suggests that one reason is that Eighth Amendment jurisprudence does not contain a well-defined doctrinal framework for courts to use in considering a prison's proffered "legitimate penological interest" in a given condition of confinement, including prolonged supermax confinement. In this Essay, we explore the idea that the federal disability discrimination statutes may offer a more tailored methodology for challenging solitary confinement of mentally ill prisoners. Unlike an Eighth Amendment claim, in which a prisoner typically challenges the aggregate of supermax conditions, a disability discrimination approach requires courts to assess the individual conditions that comprise supermax confinement, a process that requires an analysis of whether discrimination is occurring vis-a-vis each component deprivation. Finally, the Essay concludes by examining the disability discrimination approach in the context of claims asserted by the Civil Rights Clinic of the University of Denver Sturm College of Law on behalf of a mentally ill man who has been in isolation for over a decade.