An often-overlooked source of big toe pain, known as functional hallux limitus, can stem from entrapment of the flexor hallucis longus (FHL) tendon. While commonly blamed on excessive foot pronation, this condition can also occur when the FHL tendon becomes trapped in the retrotalar pulley located behind the ankle. This entrapment restricts the tendon's glide, preventing the first metatarsophalangeal (MTP) joint from dorsiflexing properly during propulsion. As a result, the joint jams, leading to pain, dorsal spur formation, and the potential worsening of conditions like bunions (hallux abductovalgus) or the development of arthritis (hallux rigidus). Diagnosis is straightforward using the FHL stretch test, which compares MTP dorsiflexion with the ankle in different positions. A simple and effective treatment is the "Hoover cord maneuver," a manual technique that tractions the subtalar joint to release the tendon. This is complemented by daily bent-knee calf stretches to maintain mobility. With these conservative measures, often combined with orthotics to address any underlying pronation, most patients achieve excellent outcomes without the need for surgical intervention.