The current study examines whether risk factors associated with child externalizing behavior symptoms differ between two similar low-income urban communities, using baseline parent data of 154 African American youth (ages 9–15) participating in the Collaborative HIV-Prevention and Adolescent Mental Health Project (CHAMP) family program. Separate multiple regression analyses of each city sample indicated that greater child externalizing symptoms were associated with increasing parenting hassles for New York families (n = 46), but greater parent mental health symptoms for participants in Chicago (n = 108). Understanding such distinctions between communities is an important first step towards tailoring services to unique community needs.