Sexual victimization of students endures—especially in secondary schools—and women’s perpetration in this setting is increasingly recognized. Nonetheless, our understanding of this population and contemporary cases remains limited, and research in the Australian context is lacking. This study contributes to the evidence base and represents the first Australian study of its kind. We draw on (1) legal documents (N = 19) describing 18 established cases of female-perpetrated sexual abuse against 20 adolescent students (aged 13–17 inclusive) and (2) semi-structured expert interviews with professionals possessing specialized experience of female-perpetrated cases involving adolescent students (N = 8). These data are integrated in a reflexive thematic analysis to identify the personal, contextual, and situational antecedents of female-perpetrated cases thereby exploring the ‘why’ and ‘how’ of their perpetration. Taken together, the results indicate a key interaction between individual emotional and relational needs, environmental opportunities, and contextual tolerance. Practical implications for targeting and disrupting these dynamics are discussed.