Studies of prison masculinities have often focused on adult men and the reproduction of aggressive, dangerous masculinities, involving men’s strategic management of emotions as a survival technique. This chapter takes a different perspective, engaging with subtle emotional aspects of young prison masculinities among incarcerated men at a Swedish youth prison, and highlighting complex and multiple prison masculinities. Furthermore, by drawing on a perspective on affect as productive of subjectivities and co-constructed in interaction, this study illuminates how prison masculinities are produced through subtle affective practices in an interview setting, rather than drawn upon intentionally. The analysis reveal subjectivities and affects as emergent from intricate interactional processes, and as intrinsically intertwined with discourse. Through the young men’s talk about their childhoods and emotions, and the interviewer’s empathetic responses, a less familiar young prison masculinity emerges–one of vulnerability. Several incarcerated young men resist this position though nuanced affective practices: indifference and irritation, which appear as more automatic than as strategic enactments, in response to being empathetically positioned as affected by trauma or loss of loved ones. Furthermore, the analyses highlight the importance of considering deviant cases, such as the few young inmates who did enact vulnerability.