Port-A-Cath systems are widely used for long-term therapy in the treatment of malignancies and infection. Spontaneous migration of Port-A-Cath catheters after satisfactory initial placement is uncommon but is associated with a number of complications, including neck pain, shoulder pain, ear pain, infection, venous thrombosis, and neurological complications. We describe two cases of migration of the Port-A-Cath catheter into the ipsilateral internal jugular vein. Both received surgical reposition of the catheter with a longer one. We speculate that the migration is related to severe cough and vigorous changes of intrathoracic pressure. We also review the literature regarding such unusual complications of Port-A-Cath. Because catheter migration might be asymptomatic, monitoring the catheter position bimonthly when not used is recommended. Before a new course of chemotherapy or encountering symptoms of migration, obtaining a chest roentgenogram is essential to provide early detection and repositioning management of a migrated catheter.