We report the case of a 34-year-old female patient complaining of headaches 1 day after childbirth, initially interpreted as postdural puncture headache (PDPH) and treated successfully with an epidural blood patch. Five days later, she presented with an acute proportional right sensorimotor hemisyndrome and a new-onset left-sided headache, attributed to a venous stroke from left-sided cerebral sinus venous thrombosis (CSVT). Simultaneously, we found radiologic signs of reversible cerebral vasoconstriction syndrome (RCVS), considered asymptomatic. We administered anticoagulant therapy to the patient, and she showed full motor recovery at 3-month clinical follow-up. PDPH, CSVT, and RCVS are well-known neurologic complications during the peripartum period. All 3 conditions present with headaches, and headache features may overlap, masking co-occurrence and making accurate diagnosis (differentiation) of these diseases difficult. Each disease can potentially lead to disabling deficits, but all respond to specific treatment. Knowledge of the causes of headaches in the peripartum period, their specific clinical characteristics, and potential complications helps to prioritize and interpret diagnostic tests to offer appropriate therapy.