The role of the “wounded healer” can have positive effects for former offenders as regards desistance and social (re)integration; however, research focusing on wounded healing/peer mentoring from a gender perspective is limited. Drawing on fieldwork conducted in Swedish peer support organizations (PESOs) for former offenders and qualitative interviews with former offenders working in five different PESOs, this study analyses how masculinity and support are performed and narrated by 15 wounded healers/peer mentors (men = 11, women = 4, age range 19–60 y/o). It contributes to knowledge about gendered power dynamics of peer support by showing that while masculinity can and do function as capital in peer support work, some displays of masculinity can trigger trauma, with negative consequences for women within PESOs.