Background: Literature shows adolescence is a critical time for forming health habits and eHealth can be an effective platform for encouraging health habits. Purpose: This study seeks to understand the impact of eHealth intervention that encourages tracking multiple health behaviors on habit participation and self-rated health. Methods: Using a web-based portal, we provided incentives to a small group of high-achieving adolescents (n = 85). The group was encouraged to log health behaviors grounded in four pillars of health: physical activity, nutrition, sleep, and stress management. Surveys were distributed four times to track behaviors and self-rated health. Results: Surveys showed significant increases in nutrition, sleep, mindfulness, and self-rated health. Self-rated health consistently increased independent of the other behaviors. Discussion: Results suggest interventions such as the one described herein can engage adolescents to participate in recommended health behaviors. Further, comprehensive, positive interventions can influence adolescents' concept of self-rated health despite small increases in health behaviors. This research further demonstrates eHealth tools can be an effective way to engage adolescents in preventive health behaviors. Translation to Health Education Practice: This study guides future research by designing a multi-behavior health framework for adolescents and using eHealth as a platform for delivery.