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Recent reports indicate 97% of youth are connected to the Internet. As more young people have access to online communication, it is integrally important to identify youth who may be more vulnerable to negative experiences. Based upon accounts of traditional bullying, youth with depressive symptomatology may be especially likely to be the target of Internet harassment. The current investigation will examine the cross-sectional relationship between depressive symptomatology and Internet harassment, as well as underlying factors that may help explain the observed association. Youth between the ages of 10 and 17 (N = 1,501) participated in a telephone survey about their Internet behaviors and experiences. Subjects were required to have used the Internet at least six times in the previous 6 months to ensure a minimum level of exposure. The caregiver self-identified as most knowledgeable about the young person's Internet behaviors was also interviewed. The odds of reporting an Internet harassment experience in the previous year were more than three times higher (OR: 3.38, CI: 1.78, 6.45) for youth who reported major depressive symptomatology compared to mild/absent symptomatology. When female and male respondents were assessed separately, the adjusted odds of reporting Internet harassment for males who also reported DSM IV symptoms of major depression were more than three times greater (OR: 3.64, CI: 1.16, 11.39) than for males who indicated mild or no symptoms of depression. No significant association was observed among otherwise similar females. Instead, the association was largely explained by differences in Internet usage characteristics and other psychosocial challenges. Internet harassment is an important public mental health issue affecting youth today. Among young, regular Internet users, those who report DSM IV-like depressive symptomatology are significantly more likely to also report being the target of Internet harassment. Future studies should focus on establishing the temporality of events, that is, whether young people report depressive symptoms in response to the negative Internet experience, or whether symptomatology confers risks for later negative online incidents. Based on these cross-sectional results, gender differences in the odds of reporting an unwanted Internet experience are suggested, and deserve special attention in future studies.