Background: Florida's Healthy Start Program is a statewide prenatal screening program that aims to identify pregnant women at risk of adverse birth outcomes. However, the effectiveness of this legislatively mandated prenatal risk screening tool in predicting poor birth outcomes is unknown. This study aimed to evaluate associations between risk factors self-reported on this screening tool and adverse birth outcomes. Materials and Methods: A 1-year retrospective birth cohort at a large academic referral center was created. Risk factors reported on the tool by mothers who had a preterm or low-birthweight (LBW) infant were compared with those reported by mothers who delivered full-term non-LBW infants in bivariate and multivariate analyses. All data were extracted from maternal or infant electronic health records. Results: The Mother/Infant Dyad Screening cohort consisted of 528 dyads. We identified two items on the screening tool that significantly associated with adverse birth outcomes, but which do not currently contribute to the total risk score used to identify women for referral to preventive social services. These items were feeling alone and thinking it was not a good time to be pregnant. Conclusions: Comprehensive prenatal risk screening is an underutilized strategy in medicine. Florida's mandatory self-reported, prenatal survey can identify women at risk for poor neonatal outcomes. A more nuanced understanding how women are interpreting survey items and a re-evaluation of scoring practices may allow the tool to better serve as a model for other programs seeking to identify pregnant women at risk of poor birth outcomes.