CASE: Herein is presented a case of rupture of the A2/A3 annular pulleys of the left second toe in a 33-year-old male patient after a snowboarding injury. The injury was detected on magnetic resonance imaging (MRI) 7 weeks after the initial trauma. The patient was treated conservatively, including toe splinting, with the patient returning to his asymptomatic preinjury baseline after 6 months. CONCLUSION: Annular pulley rupture of the toes is a novel cause of prolonged forefoot pain. Clinician awareness of this unique injury and its often subtle MRI findings may help avoid delays in appropriate diagnosis and treatment.