A perfect baby is the expectation of all parents, and a perfect outcome is the mission of obstetrics. Every obstetrician dreads to hear that there is an unexpected maternal mortality and/or severe fetal injury at the hospital. The role of a perceived public expectation of perfection in obstetric medicine reflects a belief that bad outcomes in obstetrics should not be tolerated and that every maternal-fetal injury merits financial compensation and punishment. What has brought these troubling times to obstetric medicine? The drivers behind malpractice crises are the four leading interest groups in the medical-legal debate: pregnant patients and their environment (husband, parents, relatives, friends, legislators, and the media), health-care providers, insurance companies, and trial attorneys. Litigation in obstetrics is the result of a complex of events when malpractice (presumed or real) impacts on the attitude of pregnant women and their environment. In such complexity, information is mandatory but may often be misinterpreted. If messages are not tailored to the receiver's capacity, communicating well with the pregnant patient becomes crucial. Therefore, to reduce medical-legal issues in obstetrics, increasing attention and an applicable standard of obstetric care to avoid negligence and medical errors should go along with better communication with pregnant women. Communication should be clear, targeted, effective, flexible, and empathic to share a common language and decisions. This review briefly presents and discusses some of the most frequently encountered medical-legal claim cases in obstetric practice. In-depth review of pregnancy-related deaths and major morbidities can help determine strategies needed to continue making pregnancy safer.