How the Shepherd conceives of human–spirit relations leads me to examine two examples of the consequences of this entanglement of spirit possession and enslavement. I point first to how the holy spirit in the Shepherd functions similarly to the Roman enslaved overseer (vilicus) who represents the physically absent enslaver and surveils other enslaved persons. The Shepherd solves the problem that despotic writers (e.g., Cato, Columella) lament regarding how to guarantee that the vilicus is not mistaken for the absentee enslaver: God becomes both the enslaver and the vilicus, the ever-present surveillance over the enslaved through spirit possession. I also focus on one tricky passage in the Shepherd, a parable about an enslaved person working on a vineyard and its complex layers of interpretations offered by the Shepherd (Similitude 5), to better understand how the Shepherd conceptualizes the relationship between the holy spirit and the flesh that it treats as a vessel. I show how the Shepherd views enslavement to the holy spirit as a necessary risk for the enslaver, since the spirit can be polluted and defiled if the enslaved body in which it dwells is not constantly maintained.