The paper examined the effectiveness of an in-school intervention for adolescents designed to target emotional regulation skills related to risky behaviors. The Cognitive Emotion Regulation Intended for Youth (CERTIFY) program was delivered to at-risk adolescents in Montreal, Canada. Participants were drawn from an alternative high school and a dropout prevention program within an urban high school. The pilot was a student-focused therapeutic modality without parental intervention for maladaptive cognitive emotion regulation (CER) and engagement in risky behaviors. CERTIFY is a school-based group intervention targeting CER strategies and was implemented with 28 adolescents from two English language secondary schools. The intervention was conducted for 12 weeks for the intervention group versus controls who were offered usual school supports. Program outcomes were evaluated using the Cognitive Emotion Regulation Questionnaire and Risky Behaviors Questionnaire for Adolescents. The intervention group made significant gains with regard to using adaptive CER strategies. Specifically, the intervention resulted in increases in self-reported use of positive reappraisal and refocusing on planning. No significant gains were found for reducing the use of maladaptive CER strategies or risky behaviors. This school-based intervention program for high-risk adolescents increased overall use of adaptive CER strategies and provided insight for future intervention design.