This study identified homelessness, substance use, employment, and mental health correlates of homeless youths' arrest activity in 5 cities. Two hundred thirty-eight street youth from Los Angeles, Austin, Denver, New Orleans, and St. Louis were recruited using comparable sampling strategies. Ordinary least squares (OLS) regression results reveal that being arrested for criminal activity is associated with length of homelessness, history of juvenile detention and incarceration, receiving income from theft, substance abuse, and mental illness. Arrests are also associated with interactions between lack of formal employment income and receiving income from theft and between drug and alcohol abuse/dependency. Understanding the health and situational factors associated with homeless youths' delinquent activity has implications for providing more comprehensive health, mental health, and substance abuse services.