The goal of this study was to examine whether, in African American families with adolescents, the associations between adolescents' racial discrimination experiences and adolescents' internalizing and externalizing problem behaviors differed based on involved-vigilant parenting and the genders of the parent and child. The sample included 567 African American parents of adolescents who completed an online survey on parenting, race-related stressors, and adolescent outcomes. Path analyses examining main effects and the interaction between adolescents' racial discrimination experiences, as reported by the parent, and involved-vigilant parenting were conducted in MPlus 8.2. Multigroup analyses by the gender pairing of the parent and target child were also conducted. Adolescent racial discrimination experiences were positively related to internalizing and externalizing problem behaviors. Multigroup analyses indicated that high maternal involved-vigilant parenting buffered the association between girls' racial discrimination experiences and problem behaviors whereas high paternal involved-vigilant parenting buffered the association between boys' racial discrimination experiences and problem behaviors. Overall, the results indicated that when adolescents experienced high levels of racial discrimination, involved vigilant parenting was protective for problem behaviors when received from same gender parents. Involved-vigilant parenting was compensatory when received from cross-gender parents.