The wide expansion of community supervision has resulted in large-scale reliance on probation officers to facilitate change among both youth and adults. This is especially true for supervising high-risk populations, such as gang-involved individuals. To understand how probation officers balance the dual goals of public safety and rehabilitation, in-depth interviews with 12 youth and adult officers in Oregon were conducted. Results revealed that both groups had a shared understanding of gang pathways and desistance barriers. However, they held differing views on the factors that drive success and compliance. Youth officers utilize therapeutic philosophies and emphasize restoration through community resources to help youth desist from gang activity. Adult officers endorse law enforcement philosophies, emphasize accountability and personal choices, and center punitive strategies when using interagency collaboration. This study contributes to the literature on role perceptions and decision-making, and suggests that continuity of care in supervision philosophies can yield more successful outcomes for high-risk youth and adults.