In a sample of over 700 high‐school sophomores, a jive‐category measure of family structure is found to be not related to either frequency or seriousness of self‐reported illegal behavior, except for unusually high delinquent behavior by boys from mother/stepfather homes. On the other hand, family structure does show an overall association with self‐reported trouble with police, school, and juvenile court officials. Specifically, while boys (not girls) with stepfathers admit the most delinquent acts, controlling for the amount of admitted delinquency shows that officials are more likely to respond to the misbehavior of children (especially girls) from mother‐only families. None of these findings are accounted for by race, social class, the quality of parent‐child relationships, or the quality of school