On 14 April 1816, enslaved men and women in the British sugar colony of Barbados erupted in a well-planned revolt that ever since has been known as Bussa’s Rebellion. The British responded rapidly, and with severity. They declared martial law, executed almost 150 men, and transported over 100 more. My paper will open with an examination of the fate of these ‘slave-convicts’. Spanning the British colonies of Honduras, the Bahamas and Sierra Leone, I will explore the relationship between penal transportation, enslavement, imperial governance and repression in the first decades of the nineteenth century. I will then go on to contextualise the 1816 rebellion and its associated penal transportations within the larger history of convict connections, spanning the Caribbean, Bermuda, Britain, the Australian colonies, and British India. Finally, the paper will focus on some of the global impacts of the Bigge and Molesworth reports, which in the 1820s and 1830s were critical of the convict colony of New South Wales. Linking these to both the abolition of slavery in Britain’s West Indian colonies in 1834, and to growing anti-transportationism across Empire, I will discuss debates about a new penal colony for the Caribbean, and in particular the important penal settlement of Mazaruni, in British Guiana. This was established in 1843, when the governor described it as ‘the most perfect example for convicts of any part of the colonial empire of Great Britain’.