We present the case of failure of internal fixation of a humerus fracture resulting from longitudinal fissuring of the far cortex from linearly placed screws. Our case involves a 60-year-old right hand-dominant male who underwent open reduction and internal fixation of a left midshaft humerus fracture (Orthopaedic Trauma Association Type 12-B2) with an ipsilateral Bado Type I Monteggia fracture after being struck by a motor vehicle while crossing the street. Our patient's fixation subsequently failed, which was found intraoperatively to be caused by a stress riser along the far cortex from linearly place screws.