School-based peer-to-peer sexual harassment (SH) emerged as an issue of concern in the early 1990s. As a developing field, this literature has several notable gaps. The current study extends previous research by, (a) exploring the understudied experiences of middle school students, (b) assessing students' experiences witnessing SH, and (c) evaluating how SH is related to students' emotional well-being and academic outcomes. Survey findings indicate that the vast majority of middle school students are both SH targets and witnesses. SH experiences were negatively associated with psychological well-being and academic performance. Psychological distress mediated the relationship between direct SH and academic outcomes; however, no significant relationship was found between witnessing SH and psychological or academic outcomes. Students' incident reports offered insight into the context of SH. Most perpetrators are male, victims are both male and female, and SH occurs in public spaces with few adult witnesses. Implications for research, practice, and interventions are discussed.