BACKGROUND: Detailed reviews of closed malpractice claims have provided insights into the most common events resulting in litigation and helped improve anesthesia care. In the past 10 years, there have been multiple safety advancements in the practice of obstetric anesthesia. We investigated the relationship among contributing factors, patient injuries, and legal outcome by analyzing a contemporary cohort of closed malpractice claims where obstetric anesthesiology was the principal defendant. METHODS: The Controlled Risk Insurance Company (CRICO) is the captive medical liability insurer of the Harvard Medical Institutions that, in collaboration with other insurance companies and health care entities, contributes to the Comparative Benchmark System database for research purposes. We reviewed all (N = 106) closed malpractice cases related to obstetric anesthesia between 2005 and 2015 and compared the following classes of injury: maternal death and brain injury, neonatal death and brain injury, maternal nerve injury, and maternal major and minor injury. In addition, settled claims were compared to the cases that did not receive payment. χ2, analysis of variance, Student t test, and Kruskal-Wallis tests were used for comparison between the different classes of injury. RESULTS: The largest number of claims, 54.7%, involved maternal nerve injury; 77.6% of these claims did not receive any indemnity payment. Cases involving maternal death or brain injury comprised 15.1% of all cases and were more likely to receive payment, especially in the high range (P =.02). The most common causes of maternal death or brain injury were high neuraxial blocks, embolic events, and failed intubation. Claims for maternal major and minor injury were least likely to receive payment (P =.02) and were most commonly (34.8%) associated with only emotional injury. Compared to the dropped/denied/dismissed claims, settled claims more frequently involved general anesthesia (P =.03), were associated with delays in care (P =.005), and took longer to resolve (3.2 vs 1.3 years; P <.0001). CONCLUSIONS: Obstetric anesthesia remains an area of significant malpractice liability. Opportunities for practice improvement in the area of severe maternal injury include timely recognition of high neuraxial block, availability of adequate resuscitative resources, and the use of advanced airway management techniques. Anesthesiologists should avoid delays in maternal care, establish clear communication, and follow their institutional policy regarding neonatal resuscitation. Prevention of maternal neurological injury should be directed toward performing neuraxial techniques at the lowest lumbar spine level possible and prevention/recognition of retained neuraxial devices.