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The astonishing growth in the United States’ incarceration rate has received widespread attention in recent years. State governments have been gradually implementing reforms, and we are seeing uneven declines in state prison populations across the country. However, a related trend—the massive growth of the number people supervised by probation and parole agents—has received comparatively little attention. 4.5 million people are on parole or probation in the United States and far more people are under community supervision than are in prison. Drawing from 50 interviews with a random sample of parole agents in three Midwest counties, I examine the decisions parole agents make during their everyday work routines and how these choices influence the trajectories of individuals on parole after prison. Specifically, I focus on how competing narratives concerning protecting public safety versus providing support to formerly incarcerated people shape the everyday work of agents. Further, findings reveal how these competing pressures agents encounter in turn affect the increased use of jail as sanction that has accompanied the recent decline in the country’s prison population. I find that the gradual shift away from more punitive prison sentencing polices obscures the problem of a large population under parole supervision experiencing challenges after prison and subsequently entering jail for periods of time ranging from two days to three months as a result of custodial sanctions administered by agents. This practice carries with it its own negative consequences for the lives of people returning from prison, even in the era of de-incarceration.