This article offers an overview of os trigonum syndrome, complications, operative techniques, and the authors’ preferred protocol. Os trigonum is an ossicle like many other ossicles in the foot and ankle. Individuals who require repetitive plantarflexion of the ankle for activity may develop symptoms of an enlarged os trigonum. Usually, symptoms will be isolated to the posteriolateral aspect of the ankle. Because of the normal anatomic route of the flexor hallucis longus tendon, its range of motion may also elicit pain to the posterolateral ankle. Conservative, as well as surgical including both endoscopic and open excision, has been described.