Objective: Smoking cessation during pregnancy is a modifiable intervention that can improve maternal and neonatal outcomes. Encouraging smoking cessation is an assessed measure of the Meaningful Use incentives to ensure best practices with the increased use of the electronic medical record (EMR). Physician EMR prompts have been used shown to be successful with preventive care but there is a paucity of data evaluating prompts within obstetrics. The objective of this study is to determine the effectiveness of enhanced smoking cessation prompts in a prenatal EMR. Methods: A retrospective cohort study of an enhanced smoking cessation prompting system within our prenatal EMR was performed. Pregnant women who reported tobacco use at first prenatal visit were included. The number of times a smoking cessation method was offered and documented, the number of documented attempts at smoking cessation, and the final number of cigarettes smoked were compared pre and post the enhancement of the smoking cessation prompting system. Results: 95 patients were included (48 pre-enhancement; 47 post-enhancement). Post-enhancement, the documentation of smoking cessation method offered increased (0 vs. 1, p = 0.03) and documentation of smoking cessation attempts increased (1 vs. 2, p = 0.006). There was no change in the final number of cigarettes smoked (p = 0.9). Conclusions: Enhanced prompting systems increase documentation related to smoking cessation with no change in number of cigarettes smoked. In the era of Meaningful Use guidelines which focus on documentation in the EMR, continued research must be done to assure that software enhancements and improved documentation truly result in improved patient care.