This chapter focuses on the relationality been enslavement, punishment, and convict mobility in the French, Spanish and British empires in the Caribbean, into the 1870s, arguing for an interconnected approach to punitive European geopolitics. Following the Haitian Revolution and the closure of Spanish colonies to enslaved convicts from other polities, British judicial process used penal transportation to the distant colonies of New South Wales and Van Diemen’s Land. During the 1830s, however, they were closed off following the development of anti-transportation sentiments. At this time, Britain’s West Indian colonies had for some years been interested in the establishment of a penal colony in the Caribbean region. Anti-transportation ideas reignited these debates, and British Guiana and Trinidad each established remote, inland penal settlements, but only for locally convicted felons. The chapter notes that in discussions about the abolition of the slave trade at the turn of the nineteenth century, pro-slavery campaigners justified it through the comparison of judicial enslavement and penal transportation. This provides important background for understanding the use of the language of enslavement more generally as a rhetorical device in broader debates about the abolition of transportation and its aftermath in the Caribbean.