Posterior ankle impingement and flexor hallucis longus (FHL) tendon disorders are important clinical entities that commonly affect individuals engaged in activities requiring repetitive plantar flexion, such as dancers and soccer players, but can also be encountered in the general population. Posterior talar prominences, an os trigonum, and the narrow fibro-osseous tunnel through which the FHL passes predispose the region to mechanical impingement during plantar flexion, leading to pain, restricted motion, and decreased performance. Diagnosis is often guided by a detailed history and physical examination, while magnetic resonance imaging (MRI) and, when necessary, diagnostic injections play a key role in identifying the underlying pathology. Initial management typically consists of conservative measures, including rest, activity modification, physical therapy, and injections. However, in highly active patients or in chronic, persistent cases, surgical intervention may become unavoidable. Minimally invasive arthroscopic techniques have become increasingly favored due to their low morbidity, faster rehabilitation, and earlier return to sport, making them a prominent component of modern treatment algorithms.