Although youth probation (in some countries described as youth justice or youth offending work) has been widely discussed in older and more recent criminological literature, less attention has been paid to youth probation officers’ accounts of their attitudes and strategies. In this study, the author uses in-depth interviews with 20 youth probation officers in Toronto, examining officers’ attitudes toward the youth they work with and how these attitudes are reflected in the strategies that the officers use to achieve their professional goals. Findings reveal that the officers balance their authoritative and supportive roles not only to hold youth accountable, to encourage them to assert control over their lives, and to maintain optimism about the possibility of a nondeviant life, but also to assist the youth in attaining the means and resources necessary to make positive changes. These findings are interpreted within the framework of Canadian youth justice legislation as well as the broader desistance literature.