We report a case of a 38-year-old gravida 12 multiparous African-American woman with a history of six termination of pregnancies (TOP), five term uncomplicated normal spontaneous vaginal deliveries (NSVD), fibroids, gastroesophageal reflux disorder (GERD), and obesity presented at 23 weeks gestation by dates. The patient presented with contractions, 3 hours of worsening lower abdominal pain, and three episodes of vomiting. She denied vaginal bleeding, spontaneous rupture of membranes, or fetal movements. Her body mass index (BMI) was 31.3; rest of her vitals was within normal limits. The cervical ostium was dilated to 5 centimeters and was 100% effaced, station was +3; membranes were bulging, and the presenting part was high and not palpated. The prenatal labs were within normal limits. The patient was admitted to the labor and delivery unit and started to push. Antenatal steroid therapy was not administered due to the rapid progression to delivery. The patient delivered an extremely preterm viable female at 23 weeks with an intact placenta contained within the amniotic sac as a unit “en caul.” The amniotic sac was immediately torn, and a female newborn was extracted, emergently assessed, and managed by a neonatologist. The amniotic fluid was clear with no visible abnormalities. The delivery of the infant with placenta took 26 minutes. The newborn’s Apgar scores were 4, 6, and 8 at 1, 5, and 10 minutes, respectively. No lacerations or tears were noted, and the fundus of the uterus was firm. The female newborn was transferred via airlift to a regional tertiary care hospital for emergent management of extreme prematurity, respiratory distress, thermoregulation, and the possibility of sepsis. The female infant began to deteriorate at day 4 after birth. She was intubated, ventilated, placed on an insulin drip for hyperglycemia, and given a stress dose of hydrocortisone and dopamine for hypotension. Broad-spectrum antibiotics were administered for probable sepsis, and blood cultures were drawn. Nitric oxide was administered at this point due to pulmonary hypertension with maximal setting and 100% fraction of inspired oxygen (FiO2); the infant had an oxygen saturation of 63%. Thereafter, she was transfused with packed red blood cell (PRBC) and platelets due to anemia and thrombocytopenia. An urgent head ultrasound displayed a severe grade three intraventricular hemorrhage bilaterally with an early grade four bleed in the left cerebral hemisphere. With a small window for survival and likely devastating neurological deficit, care was withdrawn from the infant after agreement between the parents and physicians. The child was pronounced dead at day 5 of life.