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Responses to sexual harassment (SH) within policing are often directed at reforming individuals as opposed to addressing systemic organizational factors. In this paper, we argue that part of the issue is the tendency of police leaders to rely on the “rotten apple” theory of police misconduct and their own assumptions about SH rather than consider the perspectives of organizational members. Through secondary survey data collected from a large North American law enforcement agency experiencing extensive complaints of SH, we illustrate the challenges of the “rotten apple”, leader centric approach, highlighting how employee sensemaking can provide important insights about the differing interpretations of SH, perceived factors enabling it to persist, and potential issues with misaligned and compliance-driven solutions. More than a decade later, data collected from the same agency reveals several enduring themes, including a fear of speaking up, the influence of the “boys’ club”, distrust in leadership, bullying and harassment, and growing backlash against a “woke” mandate. These results demonstrate the value of sensemaking in helping create a shared understanding of SH and facilitating more targeted solutions. Further, the study highlights the importance of sensemaking as part of an ongoing process of police reform.