We present the case of a 39-year-old woman with postpartum cerebellar infarction (CI) following spinal anesthesia for cesarean delivery. The patient experienced mild headache after postoperative day 1 and returned on postoperative day 6 with a severe headache. For the subsequent 3 days, she underwent conservative treatment for presumed postdural puncture headache (PDPH) before neurologic decline and diagnosis of CI on postoperative day 9. She subsequently underwent craniotomy and debridement of necrotic tissues. Prolonged or position-independent postpartum headache should prompt broadening of the differential diagnosis beyond PDPH to include other more rare but serious causes of postpartum headache.