Background: Intrahepatic cholestasis of pregnancy (ICP) is the most prevalent hepatic disorder exclusive to pregnancy, associated with significant maternal morbidity and increased risk of adverse perinatal outcomes. Recurrence in subsequent pregnancies and comorbidities such as gestational diabetes and hypertensive disorders further complicate clinical management. This case presentation, an attempted to describe the diagnostic and therapeutic challenges in managing recurrent ICP, especially in the context of overlapping maternal comorbidities and limited diagnostic resources. Case Presentation: A case of a 32-year-old Iranian woman, gravida 3 para 2, with a history of one intrauterine fetal death and one neonatal death, was ultimately diagnosed with recurrent ICP. In her third pregnancy, elevated bile acid levels were confirmed by routine monitoring from 20 weeks’ gestation, peaking at 333 µmol/L by 32 weeks. Despite intensive medical therapy including ursodeoxycholic acid, hydroxychloroquine, corticosteroids, and low-molecular-weight heparin, her pruritus worsened and bile acid levels escalated, prompting preterm cesarean delivery. The neonate experienced complications, including respiratory distress, suspected Hirschsprung’s disease, sepsis, and hyperbilirubinemia. Management included continuous positive airway pressure (CPAP), broad-spectrum antibiotics, surgery, phototherapy, and parenteral nutrition. Multidisciplinary intervention enabled neonatal recovery, and maternal symptoms resolved postpartum. Conclusion: This case underscores the complexities of managing recurrent ICP, particularly in resource-limited settings. It highlights the critical need for early diagnosis, vigilant monitoring, and a multidisciplinary approach to mitigate the risk of stillbirth and improve perinatal outcomes. Additionally, it suggests that recurrent ICP may present earlier or with greater intensity in subsequent pregnancies, necessitating more comprehensive surveillance and tailored management strategies for affected mothers.