Chronic iliac vein occlusions and post-thrombotic syndrome (PTS) are the major sources of life affecting symptomatic iliocaval venous obstruction contributing to the morbidity of chronic venous insufficiency and venous hypertension. Venous stenting is a treatment option for the management of PTS. Despite dedicated venous recanalization technologies, long-term patency rates of venous stents are still a matter of debate. Beside that, salvage of an occluded stent could be problematic or even impossible. It may be challenging to advance the balloon catheter distally to the occlusion, even after the lesion has been crossed with a guide wire. Here we describe a new technique for overcoming such difficult bottlenecks. In a supine patient, despite successful wire-recanalization of the vena cava, achieved after a popliteal access, the balloon catheter could not be passed through an occluded iliac vein stent and towards the vena cava. Consequently, the tip of the 260 cm wire, was retrieved with a snare from the vena cava and externalized through sheath inserted in the right jugular vein. Two separate balloon catheters were loaded over the two ends of the through and through guide wire and torque devices were used to lock at their exit ports. Occluded segments were afterwards crossed with the novel ‘Winching technique’ by pulling the balloon catheter instead of pushing it. We believe that this technique can speed up and facilitate the procedure for the occlusions that can be laborious to reanalyze by conventional methods.