Totally implantable venous access system (TIVAS) are widely used for various indications including chemotherapy infusion. The use of TIVAS is associated with number of complications that can occur as early as the time of insertion or can take place months later. We report a case of a 64 year old female with recurrent osteosarcoma of the mandible. She had a port-a-catheter placed for chemotherapy infusion. The patient developed fistula between the Innominate Vein and the trachea, which found to be secondary to a spontaneous migration of the tip of the catheter. To our knowledge this is the first case of this kind to be reported. This complication, although very rare, can be life threatening, and should be considered when there is a malfunction of the TIVAS.