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This study examines how punishment is structured and interpreted within a secure reentry setting. Although reentry programs are often framed as supportive and rehabilitative, they also involve supervision, monitoring, and rule enforcement that can function as punishment, creating tension in how these practices are understood and experienced in everyday life. Drawing on qualitative interviews with residents and staff, along with observations in a Nordic-inspired reentry center, this study explores how institutional practices are both structured and interpreted. Guided by penal consciousness (Sexton, 2015) and street-level bureaucracy (Lipsky, 1980/2010), the analysis focuses on how meaning is shaped through institutional roles, expectations, and interactions. Instead of assuming a clear boundary between support and punishment, this study examines how punishment is negotiated and experienced in practice. Comparing staff and resident interpretations highlights where perspectives align and where they diverge. The findings show how reentry settings operate as hybrid spaces where support and control coexist, complicating the boundary between care and punishment.