This dissertation explores the politics of prison reform and the intersections between the carceral state and the family in postcolonial India. The Indian state has publicly distanced itself from colonial legacies of punishment through its experiments with community-involved prison reform. These include informal counseling projects with citizen collectives and the popularization of the open prison. Open prisons are mix-gendered institutions where prisoners live with their families without material barriers against escape, allowing them to go out to earn livelihoods in the surrounding community. Each of these projects prescribe prisoner rehabilitation as a return to the family- which is envisioned as a catalyst for moral transformation from prisoner to reformed citizenry. However, I contend that this return is difficult in practice as a large section of prisoners’ offenses are situated in conflicts within the family and between stratified communities on matters of marriage, land, and property. Prisoners experience, contest and redirect state reforms and broader regimes of familial confinement through strategic negotiations with prison staff and community actors. I argue that through these gradual and everyday engagements, they refashion their identities, shape their lived environment and articulate new meanings of community and belonging from below. By drawing on prisoners’ narratives of captivity, mobility, and freedom, this dissertation brings analytical attention to informal spaces and practices of confinement beyond the prison, in welfare institutions such as shelters and people’s own homes across the city. Ultimately it recasts reform and rehabilitation with a relational perspective that centers the modes of engagement between prisoners, prison administrators and community actors, to identify networks and improvised spaces of care that create opportunities for the renegotiation of criminalized identities.