In South Africa, working-class communities continue to suffer from the devastating impact of maternal and infant mortality. As part of the National Health Insurance pilot programme, the District Clinical Specialist Team members were tasked with improving reproductive healthcare services and decreasing the number of maternal and infant deaths in public health facilities. The programme aimed to provide clinical training to healthcare professionals, equipping them to manage obstetric complications. This chapter evaluated the experiences of District Clinical Specialist Team members during the National Health Insurance pilot programme in the Tshwane District. Findings from qualitative in-depth interviews indicate that the clinical training provided by members empowered doctors and nurses to manage complex deliveries and care for sick infants at the primary level of healthcare. The programme also increased antenatal care visits and exclusive breastfeeding rates while reducing the number of premature births and stillbirths. However, the District Clinical Specialist Team members expressed that the most challenging aspect of their job is reviewing the death of a baby. The recurring infant deaths in public health facilities were attributed to administrative obstacles, such as delays in procuring essential medical equipment and medicines, a lack of accountability systems for infant deaths, a high turnover of medical professionals, and inadequate obstetric care services. To effectively address maternal and infant mortality, the National Health Insurance policy must prioritise eliminating healthcare system barriers and allocate the country’s financial resources equitably. This approach will ensure that women from all socioeconomic backgrounds have access to life-saving, high-quality reproductive health services.