Chronic ankle instability is a complex condition that frequently develops after recurrent lateral ankle sprains and is characterized by persistent mechanical laxity, neuromuscular deficits, and recurrent episodes of the ankle “giving way.” Beyond functional impairment, chronic instability alters normal ankle biomechanics, increasing talar tilt, anterior translation, and abnormal joint loading. These changes predispose the talar dome to focal osteochondral damage, most commonly on its medial aspect. Limited vascular supply and sustained mechanical stress contribute to the persistence and progression of osteochondral lesions, establishing a pathophysiological continuum that may culminate in post-traumatic osteoarthritis if not appropriately managed. Comprehensive evaluation requires a structured approach that integrates detailed history taking, physical examination, functional assessment tools, and advanced imaging. Clinical features such as recurrent sprains, persistent deep ankle pain, swelling, locking, and catching raise suspicion for associated intra-articular pathology. Physical examination maneuvers, including the anterior drawer and talar tilt tests, help identify mechanical instability, while functional scoring systems quantify activity limitations. Imaging modalities, such as weight-bearing radiographs, magnetic resonance imaging, and weight-bearing computed tomography, provide essential information regarding ligament integrity, cartilage status, and subchondral bone architecture. Diagnostic arthroscopy may serve both confirmatory and therapeutic purposes in selected cases. Management strategies must be individualized according to instability severity and lesion characteristics. Early-stage disease may respond to structured neuromuscular rehabilitation, proprioceptive training, bracing, and selected biological adjuncts. Persistent mechanical instability often requires anatomic ligament repair or reconstruction. Osteochondral lesions demand lesion-specific surgical strategies, and simultaneous correction of instability and cartilage damage may optimize functional recovery and reduce long-term degenerative risk.