The present study examined the link between sexual orientation and adjustment in a community sample of 97 sexual minority (gay male, lesbian, bisexual, and questioning) high school students, taking into account their experiences of peer victimization and social support within peer and family contexts. Adolescents were identified in a large-scale survey study conducted at 5 high schools. They were matched to a comparison sample of their heterosexual peers. Sexual minority adolescents reported more externalizing behaviors and depression symptoms than heterosexual youth. Compared to their heterosexual peers, sexual minority youth reported more sexual harassment, more bullying, less closeness with their mothers, and less companionship with their best friends. There were no significant differences between gay male, lesbian, bisexual, and questioning adolescents. Overall, both victimization and social support mediated the link between sexual orientation and psychosocial symptoms. Among sexual minority youth, the link between social support and externalizing was mediated by experiences of peer victimization. These findings highlight the contextual risk and protective factors associated with non-heterosexual sexual orientation in accounting for the emotional and behavioral problems in this population.