We present the case of a 60-year-old woman with a Hill-Sachs lesion caused by an anterior shoulder dislocation (SD) as a result of her falling on her left shoulder at a local restaurant. While the diagnosis of an anterior SD is commonplace, the involvement of a Hill-Sachs lesion can complicate the treatment needed to manage the SD. Crucial aspects of treatment include performing closed reduction followed by acute immobilization in a timely manner and prompt consultation with orthopedic surgery.