Tolosa–Hunt syndrome is a rare, cause of reversible and painful ophthalmoplegia characterized by recurrent unilateral orbital pain, ipsilateral oculomotor paralysis and prompt response to steroids. We describe a patient who presented with painful ophthalmoplegia and was ultimately diagnosed via contrast enhanced magnetic imaging resonance studies and was successfully treated for Tolosa–Hunt syndrome. High index of suspicion of the disease allows for immediate intervention and thus decrease the length and severity of symptoms .We describe the case presentation and keys for diagnosis emergency medicine that physicians should know for this potentially devastating condition.