Totally implanted central venous port systems are widely used to access central veins for patients needing long-term therapy. These devices have low rates of complications and are commonly used to administer medications like chemotherapeutic agents. Spontaneous rupture of a catheter segment is a rare mechanical complication, usually belatedly diagnosed and presenting with complications. We present a case of a spontaneously ruptured chemotherapy catheter diagnosed using a novel approach via oblique projections on chest X-rays and successfully removed using an endovascular approach.