Posterior ankle pain is a common complaint, and the potential causative pathologic processes are diverse. The constellation of these numerous etiologies has been collectively referred to as posterior ankle impingement syndrome. The pain associated with posterior ankle impingement is caused by bony or soft tissue impingement of the posterior ankle while in terminal plantar flexion. This condition is most frequently encountered in athletes who participate in sports that involve forceful, or repetitive, ankle plantar flexion. This article discusses the associated pathology, diagnosis, conservative treatment, and surgical techniques associated with flexor hallucis longus and posterior ankle impingement syndrome.