This chapter examines the phenomenon of what he terms repeat rebels, or episodes of enslaved people who involved themselves in more than one slave insurrection. Historians have long known about how news and information spread rapidly throughout the Atlantic world, and pivotal work has been done to show how revolutionary rhetoric, especially that emanating from Saint Domingue, spread throughout Black communication networks and inspired new waves of slave rebellion throughout the littoral to include the Gulf South. However, scholars know much less about the experiences and strategies of rebels who survived their violent attempts to overthrow chattel slavery when their revolts all too often failed and after White authorities meted out heavy-handed punishment. Yet a survey of Atlantic slave revolts from the end of the seventeenth century through the Age of Revolutions reveals that there were numerous episodes of rebellion in which at least one rebel was previously involved in another insurrection. Justin Iverson’s analysis of these repeat rebels shows us how people transferred not only the news of slave insurrection but also their rebellious experience to new shores in the Atlantic and how they prepared others to challenge the transatlantic chattel system themselves.