Subtalar instability is challenging to diagnose. It rarely follows a complete subtalar dislocation, an event more likely to result in subtalar pain, stiffness, and arthritis. By history, subtalar instability can be suggested by the patient’s feeling of ankle instability, easy “rolling over,” and a need to look at the ground constantly when walking. Clinical measures for inversion and eversion do not accurately reflect isolated subtalar motion, as soft tissue and other joint motion confound the examination. Stress radiographs have high false positive rates. Magnetic resonance imaging can show injured or disorganized ligaments suggestive of recurrent subtalar strain, but are not dynamic studies and cannot alone diagnose instability. Operative treatment, when elected, should focus on determining the source of the problem. Generally direct repair of the lateral ligaments is sufficient. Bony malalignment should always be considered especially in the setting when previous ligament reconstruction has failed.