In October 1860, US agent for recaptured Africans John Seys paid five dollars to S. S. Winkey for “arresting and delivering 4 fugitive Liberated Congoes.” Seys's seven-word phrase conveyed the contradictory situation of recaptive Africans in mid-nineteenth-century Liberia. Along with scores of other young West-Central Africans, these four fugitives had been liberated from illegal slave ships only to be captured again in flight across the Liberian countryside. The actions of these four young men—part of a broader pattern of escapes observed during the period of initial Liberian resettlement— suggest that many recaptives viewed their situation not as a legitimate form of emancipation but instead as another phase of bondage. Just as they had throughout their global exile, recaptive Africans in Liberia drew upon shipmate bonds and their West-Central African ethnolinguistic commonalities to survive and resist emancipation in the form of heavily supervised apprenticeships.

Although liberated Africans in many parts of the Atlantic basin struggled with the conditions of apprenticeship, their experiences in Liberia emerged from distinctive US slave-trade abolition laws. After banning the transatlantic trade in 1808, the US government resisted bilateral treaties that would have allowed Britain the right to search American vessels. Recaptive Africans in US custody thus came under the jurisdiction of US federal courts rather than passing through mixed commission courts such as the ones in Havana, Freetown, and Rio de Janeiro that determined the destination of the vast majority of liberated Africans. By 1819, the United States mandated the removal of recaptive Africans beyond national borders. The newly established colony of Liberia soon began to serve as the removal destination under the auspices of the American Colonization Society, which received occasional congressional appropriations for the support of slave-trade recaptives. Free and manumitted African American migrants made up the majority of Liberia's early colonial population, supplemented by occasional arrivals of African recaptives liberated from illegal slavers. By the time Liberia declared independence in 1847, the precedent of apprenticing recaptives to black American migrants (also referred to as Americo-Liberians) and missionary stations had been established. Thus, when thousands of recaptive Africans arrived during the peak years of US slave-trade suppression between 1858 and 1861, they faced conditions of apprenticeship shaped by colonial labor demands and the “civilizing” imperatives of supervising authorities.