Most women in the US have access to health care and insurance during pregnancy; however women with Medicaid-paid deliveries lose Medicaid eligibility in the early postpartum period. This study examined the association between health insurance coverage at the time of delivery and health conditions that may require preventive or treatment services extending beyond pregnancy into the postpartum period. We used 2008 Pregnancy Risk Assessment Monitoring System data from 27 states (n = 35,980). We calculated the prevalence of maternal health conditions, including emotional and behavioral risks, by health insurance status at the time of delivery. We used multivariable logistic regression to assess the association between health insurance coverage, whether Medicaid or private, and maternal health status. As compared to women with private health insurance, women with Medicaid-paid deliveries had higher odds of reporting smoking during pregnancy (adjusted odds ratio [AOR]: 1.85, 95 % confidence interval [CI]: 1.56-2.18), physical abuse during pregnancy (AOR: 1.73, 95 % CI: 1.24-2.40), having six or more stressors during pregnancy (AOR: 2.48, 95 % CI: 1.93-3.18), and experiencing postpartum depressive symptoms (AOR: 1.24, 95 % CI: 1.04-1.48). There were no significant differences by insurance status at delivery in pre-pregnancy overweight/obesity, pre-pregnancy physical activity, weight gain during pregnancy, alcohol consumption during pregnancy, or postpartum contraceptive use. Compared to women with private insurance, women with Medicaid-paid deliveries were more likely to experience risk factors during pregnancy such as physical abuse, stress, and smoking, and postpartum depressive symptoms for which continued screening, counseling, or treatment in the postpartum period could be beneficial.