Transportation of prisoners during the eighteenth and nineteenth centuries within the British Empire was principally from Britain and Ireland and typically to the Australian colonies. This article focuses on a much smaller scale of prisoner transfers by the executive, not transportation as a sentence imposed by the judiciary, between the Cayman Islands and Jamaica in the British West Indies. Such transfers were perhaps unsurprising during the period when the Cayman Islands were a dependency of Jamaica, but this practice continued during the late twentieth century following Jamaican independence. The historical development of what is now a relic of the past but still on the statute book of the present is uncovered by focusing on three distinct periods: before Jamaican independence; the period shortly after; and finally, from the establishment of a prison service to the present day. It will be argued that the colonial legacies of prison management in the late nineteenth century have pervaded until the present day, with executive power vested in the government to implement such transfers with little or no judicial oversight. Jamaican independence effectively removed any oversight relating to European Convention on Human Rights violations by a state party for prisoners relocated to another jurisdiction. Examples will be given of instances where a relatively short-term prison sentence, accompanied with a fine, has transformed into a much harsher result of incarceration overseas with inevitable, although perhaps not expressly intended, and additional punitive measures such as few family visits or a lack of any community rehabilitation and reintegration into the country of origin. This questions whether the practice of sending prisoners to Jamaica was for punishment, or as punishment, as well as uncovers legacies of colonialism in the modern era.