Chronic iliocaval venous obstructions have been treated by means of bypass surgery until endovascular treatment emerged as a valuable alternative. With the introduction of new imaging modalities, recanalization techniques and novel stent design the endovascular approach gained even more popularity and surpassed surgery as the primary treatment option. Still, lessons learned from our and others' experience launches a new era in which we should decide on some unsolved issues. Foremost, reproducible imaging techniques should help to define treatment indication. Second, further research is needed to establish the optimal stent design, but also advice on stenting techniques. Finally, if and when arteriovenous fistulas should be used to support early patency is still unclear. This manuscript addresses some of these technical considerations, pitfalls and complications to advice on materials and methods to optimize the quality of your treatment.