Objective: This study describes three techniques of stent placement at the iliocaval confluence for chronic nonmalignant obstruction and its stent-related outcome. Methods: From 1997 to 2008, 115 patients (230 limbs) underwent bilateral stenting for iliocaval obstruction. All limbs were CEAP classified using clinical examination and duplex ultrasound study. Three techniques were compared: placement of two stents side by side in a “double-barrel” (group DB, n = 39); inverted Y stenting through a fenestra (window) created through the side braiding of a stent placed previously across the iliocaval confluence (group iY, n = 38); apposition of a stent as close as possible to a stent previously placed across the iliocaval confluence, leaving a small area unsupported between the stents (group A, n = 38). Patency was assessed with venography and duplex ultrasound imaging. Cumulative patency curves were calculated. Result: Median age was 54 years (range, 14-76 years); female/male ratio was 2.8:1. Obstructions were primary in 141 limbs and postthrombotic in 89, and 29 required recanalization of occlusions. The C4-6 rate and ratio of limbs with postthrombotic obstruction were significantly higher in group iY vs group DB (49% and 32% [P = .049]; 47% and 28% [P = .022], respectively). The median follow-up was 12 months (range, 1-108 months) in 107 patients (93%). The overall primary, assisted primary, and secondary patency rates at 4 years were 61%, 92%, and 98%, respectively. The distribution of occluded stent systems (n = 4) and frequency of reinterventions (n = 29) were reflected in the primary and secondary patency rates for groups A, DB, and iY at 4 years (77% and 100%, 73% and 100%, and 41% and 90%, respectively). The frequency of reinterventions was significantly lower in group DB vs groups A and iY (8%, 32%, and 37%, respectively; P < .01). Conclusion: Chronic iliocaval confluence obstruction is best managed by double-barrel stenting when feasible. The apposition technique requires a high reintervention rate owing to restenosis of the unsupported segment. The secondary stent patency appears to be less in limbs with postthrombotic occlusion. Primary stent patency of nonocclusive obstruction was inferior in group iY regardless of etiology of obstruction. However, inverted Y fenestration is the only choice in delayed contralateral stenting or when the inferior vena cava is extensively involved. There is no optimal solution to the treatment of the iliocaval confluence presently, and the choice of technique is decided by the extent, site, and type of obstruction. © 2010 Society for Vascular Surgery.