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A 24+5-week preterm neonate with a severe scalp lesion was admitted to the neonatal intensive care unit (NICU) after caesarean section due to maternal chorioamnionitis (MC). An Arabin pessary had been inserted in addition to a previous cervical cerclage due to cervix insufficiency at 21+5 weeks of pregnancy (wp). At 23+5 wp, preterm rupture of membranes was evidenced. Both devices were kept to provide fetal viability. On 24+4 wp, she developed MC. Urgent caesarean section was performed. Transvaginal manual manipulation was required during the procedure. On NICU, she presented severe shock which required high-dose vasopressors and blood products. Following surgical repair, a bilateral grade IV intracranial haemorrhage was evidenced. Subsequently, it was agreed to withdraw life support. We hypothesise that MC and local infection could have acted as predisposing factors, with the presence of a pessary in the setting causing uterine contractions and its manipulation acting as a precipitating factor.