Juvenile probation work comprises a mixture of repressive and empowering strategies, since probation officers need to control young offenders’ conduct and at the same time help the offender to take responsibility and live life within the margins of society.This ambiguous nature of juvenile probation work may confuse the communication between probation officers and juveniles. Interviews with offenders of Moroccan origin and their probation officers in the Netherlands show that both parties are unhappy with the mutual communication. According to the youngsters, a restrictive policy is inevitable but might be more effective if this would go together with an empowering approach. Interactional analysis of the conversations shows that the lack of juvenile participation is caused by professional conversational dominance, as seen in topic control, poor role clarification, and a cross-examining style of the conversations.