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This article explores the process of enslavement in upper Guinea during the eighteenth and nineteenth centuries by analyzing over one hundred autobiographical testimonies from the Freedom Narratives collection. Building on work done by P. E. H. Hair in the 1960s, it argues that testimony from people who experienced enslavement are usually the only sources that can provide specific information on the process of enslavement. Information collected from these sources allows historians to discern changing patterns over time and to contextualize enslavement in regional history. The analysis suggests that before 1820 warfare was the most common mode of enslavement, fueled by the raiding of the ceddo states and the growth of the Islamic states such as Fuuta Jalon and Fuuta Toro. After 1820, kidnapping gained in importance, especially in the area near Gallinas. The article concludes with an analysis of ninety-four additional testimonies from a slave-dealing investigation undertaken in Sierra Leone in 1853–1854, which document the growing significance of children in local slavery during the waning years of the transatlantic trade.