Mispositioning in the azygos vein is a rare but hazardous complication of central venous catheterization. A patient was admitted for a dysfunctional hemodialysis tunneled cuffed catheter (TCC) placed in the azygos vein for 4 years. Computed tomography angiography revealed multiple sites of occlusion, including the superior vena cava (SVC), right and left innominate veins (IVs), and right femoral vein. Percutaneous transluminal angioplasty and a TCC replacement based on a segment-by-segment recanalizing strategy were performed. First, an 8-Fr sheath was inserted through the left femoral vein approach to retrogradely traverse the occlusive SVC followed by a guidewire extending to the occlusive left IV. A left transjugular 15-cm snare was inserted to capture the transfemoral guidewire and achieve recanalization from the left IV to the SVC. Second, a transjugular guidewire was advanced through the dysfunctional TCC yet shunted into the left IV due to the inability to cross the SVC. A left transfemoral 15-cm snare was inserted to capture the guidewire and achieve complete recanalization from the right internal jugular vein to the SVC. Balloons were passed over the guidewires to dilate the obstructive lesions sequentially, and a new TCC was inserted successfully with the tip positioned in the right atrium.