This draft chapter interrogates the shifting moral attitudes, social critiques, and practices regarding eighteenth-century transported convicts, and it explores the discursive overlap with debates on punishment and African chattel slavery. Colonists criticized convict servants as immoral contagions of crime and depravity; however, British policymakers could not agree on an alternative punishment to transportation. White authorities and convicts themselves also distanced servitude from racialized enslaving practices, but these efforts had the reverse effect; the discourse on convicts cast a brighter light on the brutal conditions in African slavery and unfreedom. While convict servitude was shaped by imperial policy, it was also a distinct practice and rhetorical tool in the deliberations on colonial labor, linking developing ideas of moral sentiment and accountability in transatlantic discourse.