Public health practice involving adolescents is largely focused on preventing or delaying the initiation of risk behavior. However, given the experimental and exploratory nature of this developmental period, this is often impractical. This article focuses on behavioral transitions and the ways in which youth involved in risk behaviors shift to more promotive behaviors. Based on a positive youth development perspective, in-depth interviews with urban youth were conducted and analyzed to gain an understanding of the influences on behavior change. Specific family support, ability to detach from harmful peer relationships, and school connectedness and vocational support emerged as important to those youths who made a positive behavioral transition. These findings suggest the importance of understanding ways to support the cessation of involvement in risk behaviors and reinforce the significance of contextual influences on youth development.