The chapter explores the lives and experiences of enslaved Africans across the island in a variety of rural contexts. Labor was often the over-arching factor that defined the experience of an enslaved person; therefore, this work looks comparatively at different types of plantations and other work environments. The chapter argues that the illegal slave trade period of the nineteenth century is vital to understanding the lives of people of African descent, as it was a sharp departure from earlier eras. It was marked by rapid expansion of the population and the plantation complex, which in turn resulted in living and working conditions that were increasingly poor over the course of the mid-century. This change would have both immediate and longer-term consequences for Cuba and its diverse and growing population.