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Popular notions of US criminal justice invoke prison gates and razor wire. Yet over half of the total correctional population—3.7 million Americans—live under community supervision on probation. 73% of all justice-involved women are serving a probation sentence. Despite being the single most common form of punishment, we know little about the lived experiences of women on probation. Often viewed as a slap on the wrist, scholarship tells us that probation is deeply punitive and hinders opportunities for mobility, especially among poor and minoritized women. Drawing on 50 interviews with women on probation in Baltimore, Maryland, this study highlights the daily hardships associated with living under community surveillance as they relate to race, class, and motherhood. Analyzing for whom probation operates as a second chance, and for whom it feels like a set up to fail, this paper contributes to our understanding of the mechanisms of life course inequality that stem from correctional sanctions.