Patients with benign solitary enchondromas of the proximal humerus frequently present to the diagnosing physician with shoulder pain. Once the lesion is considered benign, emphasis can be placed on identifying the etiology for the pain. We reviewed our experience with these patients to identify the cause of the presenting pain. A retrospective review of clinical records and radiographic studies (radiographs, magnetic resonance images, and bone scans) was done for all patients presenting to an orthopaedic oncology unit with solitary enchondroma of the proximal humerus. Attention was focused on diagnostic evidence of additional disease in the shoulder. Fifty-seven patients (mean age, 53.6 years) met the criteria of the study and were included for evaluation. Of patients presenting with pain, 82% (47 of 57 patients) had findings seen on magnetic resonance imaging scans that correlated with the initial clinical diagnostic impression, suggesting that other disease was present that could explain the pain. Solitary enchondromas of the proximal humerus often are found incidentally during the initial evaluation of patients with shoulder pain. This study showed that additional treatable disease usually is present in patients with enchondromas of the proximal humerus.