Lower extremity stress fractures are relatively common among competitive athletes. Stress fractures of the upper extremity, however, are rare and most have been reported in the literature as case reports. We present a case of an adolescent baseball pitcher who had both proximal humeral and ulnar shaft stress fractures, as well as spondylolysis of the lumbar spine. This particular patient also had an underlying endocrine abnormality of secondary hyperparathyroidism with a deficiency in vitamin D. A bone mineral density panel demonstrated a high T score (+2.79 SD above the mean) and the patient's biologic bone age was noted to be 2 years ahead of his chronologic age. The patient was treated with a course of vitamin D and calcium supplementation. After treatment, both the vitamin D and parathyroid hormone returned to normal levels. The upper extremity stress fractures and spondylolysis were managed conservatively and he was able to return to full activity and baseball. For patients who present with multiple stress fractures not associated with consistent high levels of repeated stress, a bone mineral density panel should be considered. If vitamin D deficiency is present, a course of oral supplementation may be considered in the management. An endocrinology consult should also be considered in patients who present with multiple stress fractures. Conservative management of upper extremity stress fractures and spondylolysis was successful in returning this patient back to his previous activity level.