Juveniles in secure confinement allegedly suffer from more mental health problems than their peers. This may reflect background and behavioral characteristics commonly found in clients of both mental health and juvenile justice systems. Another explanation is that mental disorders increase the risk of arrest. These interpretations were tested on a sample of Pittsburgh boys (N=736). Findings indicate that arrested youth exhibit more attention deficit hyperactivity (ADH) problems, Oppositional Defiant (OD) problems, and non-delinquent externalizing symptoms prior to their first arrests compared to their never-arrested peers. However, arrested and non-arrested youth score similarly on prior affective and anxiety problems and internalizing symptoms. Net of delinquency, substance use, and other selection factors, internalizing problems lower the risk of subsequent arrest, while OD problems and non-delinquent externalizing symptoms increase the risk of arrest. ADH problems have no effect on arrest net of delinquency and substance use. These findings lend only partial support to the criminalization hypothesis. Whereas some mental health symptoms increase the risk of arrest, others elicit more cautious or compassionate official responses.