Objective: This study examined the effects of offering proactive student-success coaching, informed by predictive analytics, on student academic performance and persistence. Specifically, this study investigated semester grade point average (GPA) and semester-to-semester persistence of community college students as outcomes. Methods: This study involved two stages of analysis. First, we used inverse probability of treatment weighting to create appropriately balanced samples of the students offered proactive assistance and students not offered proactive assistance to approximate a randomized control trial with observational data. Then, we applied regression analyses with weights and covariates to the balanced samples to estimate outcomes. Results: Using regression analyses with weights and covariates, we estimated few statistically significant results in sample subgroup models and no statistically significant results for whole-group samples. Generally, our analyses found that the offer of the intervention had no effect on students’ persistence and semester GPAs. Conclusions/Contributions: This study contributes empirical results to the emerging literature regarding student-success coaching, predictive analytics, and student-monitoring systems. The results demonstrate the necessity of performing rigorous analyses on these predictive-analytic systems and reveals ethical concerns that should be considered in designing interventions.