Responsibilization has been seen as a major technique for society’s governing of troublesome youth, yet few previous studies have investigated responsibilization in practice. This article explores a behavior modification program at a youth detention home, specifically how involved self-assessment practices can be conceptualized as a responsibilization strategy (aimed at producing free and self-governing subjects). The study documents and explicates this complex discursive setting, where responsibilization practices are combined with rigorous control. Drawing on video-ethnographic methods, the analyses explore how responsibilization is attempted and resisted in interaction. Institutional rules and manuals were used by residents both to enact resistance and to position themselves as responsibilized, in which self-assessment practices make out a kind of technology of the self (Foucault). Further, the study concludes that both staff and residents at times strategically positioned residents as children, something that ultimately could be conceptualized as both parties jointly enacting resistance in response to the dilemmatic discursive setting.