This chapter presents the analysis with convictism and its constitutive historical themes because it brings back into focus issues such as slavery, and forced and indentured labour through practices such as blackbirding, and migration. It focuses on convictism which enables a fresh look at penal modernity and the postcolonial, foregrounding the history of colonial penality's most enduring legacy, the contemporary hyperincarceration of Indigenous peoples. The chapter examines one specific feature of convictism: that of 'secondary punishment', an issue which connects with the discussion of the rise of 'supermax' prisons and the historical legacy of high-security regimes. Transportation was also an important part of a global debate about the punishment of crime, penal philosophies and practices, and notions of reform under the influence of the Enlightenment. The interesting effects of viewing convictism through the lens of World Heritage significance are that it places transportation in the category of one of the major forms of intercontinental forced migration in world history.