This chapter focuses on young people’s compliance while subject to community supervision. It commences by exploring the types of issues that influence what constitutes compliance/non-compliance when working with young people and supervisors’ approaches to decision-making about compliance. It also explores the specific challenges that arise when supporting young people’s cooperation with community supervision. The main body of the chapter centres on discussing the skills, practices, and strategies utilized by supervisors to encourage young people’s compliance. Strategies include developing positive working relationships; communicating roles and expectations ‘front-end compliance’; addressing barriers to compliance; ownership and participation in the supervision process; and responsiveness to non-cooperation. The chapter concludes by discussing the relevance of fostering social and psychological legitimacy to encourage compliance, as well as considering possibilities of further enhancing compliance-orientated practice with young people on community supervision.