Extensive research shows that parental monitoring is a critical factor in child adjustment. Using parent and adolescent reports, this study sought to examine predictors of parental monitoring among an understudied, high-risk sample of runaway adolescents. Parent-reported depressive symptoms, couple (romantic) relationship satisfaction, and adolescent-reported bonding with parents were used as predictors of both child- and parent-reported monitoring. Findings indicated that, among parents, the couple relationship was the primary predictor of monitoring, whereas among adolescents, the parent–child relationship was the primary predictor. Maternal depressive symptoms were unrelated to monitoring. These findings suggest the utility of considering monitoring as an interpersonal phenomenon rather than primarily a parent- or child-driven phenomenon.