This study evaluated the impact of the Student Success Skills (SSS) classroom curriculum delivered in a naturalistic setting on the metacognitive functioning of 2,725 middle and high school students in Kentucky. SSS was implemented as one intervention to fulfill an Elementary and Secondary School Counseling Grant. Results in students’ self-reports indicated that those who received the intervention demonstrated increased ability to regulate their levels of emotional arousal. No additional significant differences were found. These findings differ from the results of previous outcome studies involving SSS. Implications for implementing SSS in naturalistic school settings and directions for future research are discussed.