Tolosa-Hunt Syndrome is one of the rare but easily treatable causes of painful ophthalmoplegia. It is due to nonspecific granulomatous inflammation in the cavernous sinus, supra-orbital or orbital fissure. We present a case of a middle aged hypertensive female with acute onset headache, retro-orbital pain, left sided complete ptosis, diplopia and complete ophthalmoplegia. She had no other neurodeficiet. MRI showed enlarged cavernous sinus and soft tissue enhancement on T1. After excluding other causes she was diagnosed as a case of Tolosa-Hunt Syndrome and started on oral steroids to which she responded promptly. In this article we illustrate the various causes and approach to diagnose a case of painful ophthalmoplegia with emphasis on Tolosa-Hunt Syndrome and suggest a regimen of corticosteroids.