The purpose of this article is to present a rare case report of a spontaneous fracture and embolization of a port-a-cath, known as pinch-off syndrome. This infrequent complication which is associated with placement of ports via the subclavian venous route is one of the primary reasons why surgeons and interventionalists have slowly shifted away from subclavian venous access to internal jugular venous access when considering both a safe and reliable access for port placement. Knowledge of this complication is critical to both operators placing these devices, as well as radiologists reviewing the imaging of such patients in follow up.