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In October 2003 the Supreme Court of the United States allowed Arkansas officials to force Charles Laverne Singleton, a schizophrenic prisoner convicted of murder, to take drugs that would render him sane enough to be executed. On January 6 2004 he was killed by lethal injection, raising many ethical questions. By reference to the Singleton case, this article will analyse in both moral and legal terms the controversial justifications of the enforced medical treatment of death-row inmates. Starting with a description of the Singleton case, I will highlight the prima facie reasons for which this case is problematic and merits attention. Next, I will consider the justification of punishment in Western society and, in that context, the evolution of the notion of insanity in the assessment of criminal responsibility during the past two centuries, both in the US and the UK. In doing so, I will take into account the moral justification used to enforce treatment, looking at the conflict between the prisoner's right to treatment and his right to refuse medication where not justified by outcomes that can be reasonably expected to be positive for the individual. Finally, in contrast with some retributivist arguments in favour of enforced treatment to enable execution, I will propose a possible alternative, necessary if we are to consistently uphold the notion of autonomy.