Initial validation was sought for the Life-Challenges Questionnaire-Teen Form, a 120-item youth-risk assessment tool. The questionnaire was administered to 99 students enrolled in an adolescent detention facility and a comparison group of 305 students attending high school. The survey items included correlates of youth violence and categorized risk level in a Risk Assessment Index (RAI) based on 53 critical items most strongly correlated with youth violence. Higher RAI scores were expected for the detention sample, males, minorities, and 15- to 18-year-olds. Differences between adolescents in detention and high school in terms of risk for violence were assessed by means of analysis of variance, and multiple regression analysis was used to examine the relative effect of detention status, race/ethnicity, gender, and other factors on risk behavior as measured by the RAI. Findings revealed that the detention group endorsed correlates of youth violence more often than the non-detention group and received significantly higher RAI scores. In addition, being in detention, male, and a racial/ethnic minority were significant predictors of risk behavior. The authors conclude that The Life-Challenges Questionnaire (and Risk Assessment Index) effectively differentiated between the detention and student samples, thus, providing initial support for its validity as a risk-assessment measure.