Intracranial hypotension can cause persistent and severe orthostatic headaches. It is often the result of cerebrospinal fluid leakage secondary to iatrogenic causes. It can also happen spontaneously. Diagnosing and managing severe orthostatic headaches associated with intracranial hypotension can be challenging, particularly during late pregnancy. This case describes a parturient at 30 weeks' gestation who presented with severe headaches due to intracranial hypotension caused by dural defects and cerebrospinal fluid venous fistula. She was managed with serial non-targeted epidural blood patching as a bridging remedy. This allowed further fetal maturity before delivery and definitive management of the dural leakage after delivery.