This study of two legal cases of sexual harassment investigates employee perceptions and organizational characteristics associated with policy and implementation procedures in two public school districts in New York State. Thirty-one employees involved in the investigative and litigation proceedings responded to interview questions and questionnaires. Both cases under study claimed that retaliation was exercised by district authorities. In one case it appeared to be in response to complaints of sexual harassment while in the other case it was seemingly used as a preemptive measure to facilitate the firing of an undesired employee. The findings indicate how employee expectations of personal and organizational consequences affect their interpretation of district and school leader responses to sexual harassment claims. The insufficient separation between those holding investigative authority and executive power had a chilling effect on the willingness to voice concerns in one district and facilitated retaliatory behavior in both districts, underscoring the importance of a clear separation of executive from investigative power.