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Exclusionary discipline receives considerable scholarly attention, but the concept homogenizes practices that rely on the physical detainment of youth, like in-school suspension, and practices that do not, like out-of-school suspension. In this paper, I argue that school discipline should be evaluated not only on the basis of whether it is exclusionary, but also whether it is detainment-based. I draw on three years of ethnographic observations and 108 interviews in a public high school to explore why and how students and adults differently evaluated detainment-based versus non-detainment-based practices. Although both groups drew parallels between detainment-based discipline and carcerality, adults insisted that detainment-based discipline was less “severe.” Students, however, strongly preferred non-detainment-based discipline because it released them to relative “freedom.”