Traumatic ankle conditions can lead to long-term sequelae if a pathologic process is misdiagnosed. The clinical presentation of an osteochondral lesion of the talar dome requires the clinician to have a high index of suspicion, and advanced imaging is often necessary to make the final diagnosis. Treatment should be initiated once the lesion is appropriately staged by radiologic or magnetic resonance imaging. We discuss the use of arthroscopy-assisted retrograde drilling of the medial talar dome that spares the articular cartilage within the talotibial articulation.