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In early New South Wales, madness was identified as a problem of colonial order, but there was little effort to understand it before it was sequestered. For much of the penal phase of the colony’s history, there is little evidence of definition, diagnosis, or medical treatment. Nor was there much talk of cure. My contention is that rather than a medical problem, madness was a problem across several spheres of colonial government and experience; because it was at once seen as recognizable, and in deeper ways unknown, it produced negotiation and dispute across these spheres. In many ways madness complicated and unsettled the peculiar structures and patterns of the penal colony, and the philosophies of punishment and reform driving it. The changing formulation of madness, and the solutions conceived for it, reveal the influence of the shifts in colonial and metropolitan policy, but also the sort of society which criminal transportation created: from a ‘society of felons’ to a society anxious about felonry. In the 1840s, the increasing majority of free colonists claimed madness as a problem of free society: it was made subject to medicine, and therefore to cure. In a penal colony, madness was highly political. This thesis explores these negotiations, ranging from criminal sentencing in Britain through to the peculiarities of a society of transported convicts; the complications of government policy toward the convict and free insane; the strain of competing colonial projects which might end in madness and suicide; and the politics of asylum reform in a colony reaching towards self-government. To narrate and interrogate those negotiations across 70 years, and throughout the many fields in which madness sowed, the chapters linger on a series of historical episodes. These show both the mystery of madness itself – causes, pathology, even symptoms – and the significance of responses to it. There was entanglement between personality, law, politics and the structure of empire. This study therefore illuminates colonial history in new ways as it follows a course which diverged dramatically from the path of madness in Europe.