This article explores the British Empire’s configuration of imprisonment and transportation in the Andaman Islands penal colony. It shows that British governance in the Islands produced new modes of carcerality and coerced migration in which the relocation of convicts, prisoners, and criminal tribes underpinned imperial attempts at political dominance and economic development. The article focuses on the penal transportation of Eurasian convicts, the employment of free Eurasians and Anglo-Indians as convict overseers and administrators, the migration of “volunteer” Indian prisoners from the mainland, the free settlement of Anglo-Indians, and the forced resettlement of the Bhantu “criminal tribe”. It examines the issue from the periphery of British India, thus showing that class, race, and criminality combined to produce penal and social outcomes that were different from those of the imperial mainland. These were related to ideologies of imperial governmentality, including social discipline and penal practice, and the exigencies of political economy.