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Calcific tendonitis of the gluteus medius and minimus tendons is a rare complication of hydroxyapatite deposition disease, with bilateral involvement even more so. Although patients can be asymptomatic, there is often an acute-on-chronic presentation of pain. We present a case of bilateral calcific tendonitis of the gluteus medius and minimus tendons on a background of previous bilateral rotator cuff calcific tendonitis in a middle-aged woman. This patient's long-standing history of multi-focal involvement required a multidisciplinary approach between orthopedics, rheumatology, and musculoskeletal radiology for optimal management, requiring different treatment options for different affected sites.