The purpose of this paper is to examine the effectiveness of Reconnecting Youth, a prevention program for at-risk high school youth. Data are from a large, independently evaluated effectiveness trial in two diverse urban school districts. A total of 1,218 students participated: 50% were male; average age was 15. We tested whether positive efficacy trial effects could be replicated, and whether any negative behavioral effects occur when clustering high-risk youth. Although mixed program effects were observed at immediate post-intervention, only negative effects were found at 6-month follow-up. These effects included less optimal scores on measures of GPA, Anger, School Connectedness, Conventional Peer Bonding, and Peer High-Risk Behaviors. Overall, we found little support for the use of this social-influence--model intervention aimed at increasing school connectedness for high-risk youth. Further, this study provides evidence that clustering high-risk youth in preventive interventions has the potential for iatrogenic effects.