Calcifying tendinitis occurs most commonly in the rotator cuff tendons, particularly involving the supraspinatus tendon insertion, and is often asymptomatic. Cortical erosion secondary to calcifying tendinitis has been reported in multiple locations, including in the rotator cuff tendons. The authors report two cases of symptomatic calcifying tendinitis involving the infraspinatus tendon with cortical erosion with correlative radiographic, and MR findings. The importance of considering this diagnosis when evaluating lytic lesions of the humerus and the imaging differential diagnosis of calcifying tendinitis and cortical erosion are discussed.