Herpes simplex virus (HSV) is a recognized cause of neonatal infection, with hematologic vertical spread usually only during a primary infection. This is an unusual case with hematologic spread of an HSV 2 infection resulting in a fetal stroke, not associated with a primary outbreak during pregnancy. A 25-year-old multigravida at 26 weeks was diagnosed with a large fetal stroke. Previous ultrasounds showed normal anatomy. She had preterm labor and delivery, with unsuccessful neonatal resuscitation. Vesicular lesions were noted on the infant. Both the lesions and the cerebral spinal fluid were positive for HSV 2. She had documented HSV infection prior to pregnancy, indicating that this was due to a hematologic secondary infection, as there was no rupture of membranes or evidence of other modes of transmission. This case shows that, while unusual, HSV hematologic vertical transmission can occur in both primary and secondary infection during pregnancy. Infection screening is worthwhile in unexplained fetal strokes.