We describe herein a patient who presented with painful ophthalmoplegia and was ultimately diagnosed via magnetic imaging resonance studies and successfully treated for Tolosa-Hunt syndrome. Tolosa-Hunt syndrome is a rare, reversible and painful ophthalmoplegia characterized by recurrent unilateral orbital pain, ipsilateral oculomotor paralysis and prompt response to steroids. Specific criteria for its diagnosis exist and are discussed herein. Individuals affected may display signs of select cranial nerve palsies, ptosis, facial numbness, diplopia, midrosis, and proptosis. Appropriate recognition of the disease can allow for immediate intervention and thus decrease the length and severity of symptoms especially as symptoms may not spontaneously resolve without treatment which leads to unnecessary suffering through pain, anxiety, and decreased vision. We describe the case presentation and keys for diagnosis emergency medicine that physicians should know for this potentially devastating condition.