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This article explores findings from 23 expert stakeholder interviews on working with cisgender heterosexual men and boys in the fields of gendered violence prevention, relationships and sexuality education (RSE), sexual health, sport, and emotional and mental well-being. It focuses on how organisations and individual consultants navigate political and social tensions when working with boys and young men. Findings from these interviews note several significant challenges and barriers stakeholders face in implementing programs designed to support cisgender, heterosexual boys and young men, particularly in areas of sex, sexual health and wellbeing. These include 1) broader questions as to who is responsible for teaching about sex, relationships, and sexuality; 2) the lack of public support in running programs about sex and sexuality, 3) uncertainty as to the best settings to engage boys and young men, and 4 …