The purpose of this study was to evaluate a state-wide teen pregnancy dropout prevention program using cost-benefit analysis. Data analyzed from five high schools covering a decade compared three student populations: teens from the general population, teens who were enrolled in the fully online program, and teens who selected out of the full program but made use of daycare services. Graduation outcomes and the cost per student for administering each version of the program were examined. Results revealed that students in the full program (over the 10 years) experienced a graduation rate of 1.6% with a negative rate of return of $-8,989,736; whereas, student continuing their face-to-face courses (but making use of daycare services) experienced a graduation rate of 64.5% and rate of return of $293,370. These findings demonstrate the utility of employing a cost-benefit analysis, encouraging school districts to collect more data regarding educational outcomes of pregnant and parenting teenagers to guide the efficient allocation of resources. This methodology could be adopted to inform future policy decisions aimed at increasing high school graduation rates while judiciously evaluating the investment for those interventions.