We present the rare case of a 33-year-old obese female-to-male transgender patient on exogenous testosterone since 2009 who presented with 1-month of acute on chronic headache and profuse rhinorrhea. Fundoscopic exam revealed disc edema and pallor consistent with a Frisen Grade 3 papilledema. Nasal secretion was positive for beta-2-transferrin, a marker of CSF. Computed tomography (CT) head demonstrated a 5-mm defect in the medial left middle cranial fossa consistent with a CSF leak and abnormal arachnoid granulations concerning for IIH. An endoscopic endonasal repair of the left lateral sphenoid recess leak was successful and our patient reported resolution of his acute headache. However, at 1-month follow up, our patient reported reemergence of his headache and was started on acetazolamide 250mg twice daily. At 1-month follow up after starting acetazolamide, he noted improvement in symptoms.