Neonatal herpes simplex virus (HSV) infection is usually acquired at birth. We present an infant with intrauterine HSV infection acquired after rupture of membranes. The infant was born prematurely to a woman with a first episode of genital herpetic infection in early pregnancy and rupture of membranes 11 days prior to delivery. The infant, at delivery had extensive brain damage, hemorrhage, and cystic encephalomalacia due to herpes infection. On 2nd day of life, Magnetic Resonance Imaging, suggested that the hemorrhage had occurred 7 to 14 days before the scan and the placental pathology was supportive of an ascending infection. The case of an ascending herpetic intrauterine infection after rupture of the membranes raises the question of prevention and suppressive antiviral therapy.