Britain’s practice of purchasing enslaved Africans in the Caribbean to fill these regiments is well documented, yet historians know far less about Britain’s process of turning enslaved people into West India Regiment soldiers in colonial Africa. Drawing on service records and biographical vignettes, this paper traces the odysseys of conscripted Africans from the slave ships on which they arrived in Freetown to the companies in which they served. West India Regiment recruiters awaited the arrival of recaptured slave vessels in Sierra Leone and pressured groups of Africans to enlist. Officers led new recruits to the local regimental depot for basic training, and soon after, forced them aboard transport vessels which carried them to the West Indies to join their regiments. By following the journeys of Africans conscripted into the West India Regiments in Sierra Leone, this paper demonstrates how British officials in Freetown used slave-trade abolition as a means of forcing Africans to serve in the British military. Further, it shows that for conscripted Africans themselves, “liberation” in Sierra Leone meant a life of military service to the British empire.