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The number of parents behind bars remains alarmingly high. The detention/incarceration of parents is a critical yet often overlooked issue that intersects with race, gender, and economic inequality. Drawing on semi-structured interviews with 41 detained/incarcerated parents in a large urban jail in the southeastern United States, this study examines how structural barriers shape their experiences of parenthood while confined. Thematic analysis reveals three key findings: (1) Black parents face heightened surveillance, harsher sentencing, and greater child welfare involvement; (2) gendered expectations stigmatize incarcerated mothers as failures while marginalizing fathers' caregiving roles, with LGBTQ+ parents facing additional marginalization due to biases against non-heteronormative family structures; and (3) economic precarity limits parental engagement. The study highlights the ways in which detained/incarcerated parents negotiate their roles despite restrictive policies and practices, financial hardships, and societal stigma, and calls for policies that move beyond punitive frameworks and recognize the complex realities of parenting behind bars.