Little is known regarding the predictors of arrest for homeless and runaway youth. The self-reported criminal activity of homeless and runaway youth has been associated with familial abuse, deviant peers, and situational street stressors. The path to running away was suggested to differ by gender, with more girls running away from sexually and physically abusive homes than boys. We asked two questions in our research: Are the predictors of arrest among homeless and runaway youths similar to the predictors of self reported offending and do these predictors differ by gender? Our results indicated that association with deviant peers, prior arrest, sexual abuse, and poor parental monitoring were associated with the number of arrests homeless and runaway youths reported. Yet the effects of prior arrest and deviant peers were stronger for boys, suggesting a gendered process of arrest for homeless and runaway youth.