This case involves a male patient who underwent an operative arthroscopy of the right shoulder to repair a shoulder flap lesion, biceps tear and labral tear. The post-operative diagnosis was a labral tear and synovitis. Post-operatively, the patient was found to have diminished breath sounds on the right side of his chest and an x-ray revealed a pneumothorax. He was transported by ambulance to another hospital where a chest drain was placed, and the pneumothorax had resolved two days later. Four days after the chest drain was placed, the patient was scheduled for physical therapy, but refused treatment as he was experiencing pain. He was discharged the following day. Several months later, the patient presented to an orthopedic surgeon complaining of worsening shoulder pain following the surgery despite conservative treatment and rehab. The patient had a limited range of motion in the joint. The orthopedic surgeon’s physical examination revealed rotator cuff irritation, limited abduction and forward flexion, contracture in internal and external rotation and contracture and pain in the anterior region of the shoulder. An MRI was performed, which revealed tendinopathy with severe bursitis and secondary biceps rupture that was not addressed during the prior surgery. The orthopedic surgeon’s impression was that the arthroscopy was a failure, and the patient underwent another surgery to resolve the ongoing shoulder problems.