Epidural analgesia is an efficient method of controlling pain and has a wide spectrum of therapeutic and diagnostic applications. Potential complications may occur in a delayed fashion, can remain undiagnosed, and can be a source of significant morbidity. We present a 37-year-old woman presented with severe spontaneous occipital headaches, diplopia, and dizziness that occurred spontaneously six weeks after giving birth. Her primary method of pain control during labor was epidural analgesia. Her neurologic exam revealed a cranial nerve six palsy with ptosis, and her brain MRI demonstrated a Chiari I malformation which had not been previously diagnosed. CT myelography of the lumbar spine revealed extradural contrast extravasation within the interspinous soft tissue at L1-L2, which was the site of her prior epidural procedure. She underwent epidural blood patch administration, and her cranial nerve palsy resolved along with all of her other symptoms. The development of concurrent Chiari I malformation and cranial nerve palsy after epidural anesthesia is an exceptionally rare occurrence. Neurologic complications after epidural anesthesia are likely under-reported, since patients are often lost to follow-up or have subtle neurologic signs which can easily be missed. This frequently delayed presentation emphasizes the importance of patient education and the necessity of a detailed neurological exam when symptoms occur.