<p>Umbilical cord ulceration (UCU) is an uncommon but devastating cause of acute fetal hemorrhage, often associated with fetal upper gastrointestinal obstruction. We report a woman aged 30–35 years (gravida 4, para 1) referred at 23 weeks of gestation for suspected fetal gastrointestinal abnormality. Prenatal ultrasonography showed an enlarged fetal stomach with a double-bubble sign, and subsequent examinations demonstrated progressive polyhydramnios with increasing bowel dilatation. At 32 weeks and 4 days of gestation, after previously reassuring fetal assessment, the fetal heart rate suddenly fell and remained at 90–97 beats per minute, prompting emergency caesarean delivery. A large volume of blood stained amniotic fluid was noted and a longitudinal vessel rupture at the fetal end of the umbilical cord was identified with active bleeding. The neonate had profound anemia and died after withdrawal of care. Histopathology confirmed umbilical cord ulceration with vessel rupture and erythrocyte extravasation. This case highlights the abrupt onset of UCU and supports heightened surveillance when fetal upper gastrointestinal obstruction is suspected.</p>