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Menstrual education is imperative for the health of developing females. Female youth in detention often lack menstrual health resources and report poor overall gynecological health. Scholars recognize the potential for detention to improve the health of detained youth for those who have not had regular healthcare access in the community. Despite the central role adults play in aiding youth access to healthcare, little is known about the role of detention staff in facilitating menstrual health within juvenile detention. Semi-structured interviews with juvenile detention staff were conducted to understand their perceptions, experiences, and needs when engaging with detained youth about their menstrual health. The data suggest staff comfortability when interacting with menstruating youth was often dependent on the gender of the staff member and how knowledgeable they felt about menstrual health. Participants also emphasized the need for menstrual health education for detained youth. The findings identify potential next steps for gender-specific healthcare policy and practice in detention that can increase staff confidence and comfortability when interacting with youth about menstrual health. We discuss the implications of preparing staff to engage in non-stigmatizing, factually correct, and compassionate ways of promoting menstrual health for system-involved menstruators.