BACKGROUND Intracranial hypotension secondary to spontaneous spinal cerebrospinal fluid (CSF) fistula is a rare condition that can have serious sequelae. Early diagnosis and treatment can be challenging. METHODS We present the case of a 17-year-old male who presented with a history of sudden-onset, postural headaches associated with upper thoracic back pain. Magnetic resonance imaging (MRI) demonstrated a thoracic extradural fluid collection and slumping of the brain within the posterior fossa. The patient was initially managed with a period of bed rest, followed by a thoracic epidural blood patch. Symptoms recurred and subsequent operative exploration found a large arachnoid cyst with CSF egress through a linear split in the axilla of the right T7 nerve root. The arachnoid cyst was resected, and the defect was closed primarily. All symptoms completely resolved. MRI at 3 months postoperatively demonstrated normal spinal configuration and resolution of brain sagging. CONCLUSIONS Spontaneous CSF leaks are a rare cause of postural headache. Although epidural blood patching is an easy and safe intervention, early serial imaging to ascertain the evolution of the pathology may identify cases that are amenable to early surgical management.