Iliofemoral venous outflow obstruction, arising from nonthrombotic iliac vein lesions (NIVLs) or post-thrombotic disease (PTs), is a frequent culprit behind chronic venous signs and symptoms. In response, the adoption of deep venous stenting has gained traction, demonstrating commendable technical success and acceptable complication rates in the management of both acute and chronic venous obstruction. However, the focus on venous stent failure has intensified due to concerns related to in-stent restenosis or thrombosis. Such complications elevate the risks of symptom recurrence and thrombosis relapse, necessitating a judicious approach. The identified contributors to venous stent failure encompass multifaceted factors, including insufficient coverage of the affected area, inadequate vein inflow, inappropriate stent sizing, suboptimal drug therapy, patient non-compliance, stent migration, or fracture. This paper provides a comprehensive exploration of these factors associated with venous stent failure, shedding light on the complexities surrounding the efficacy and longevity of deep venous stenting in the context of iliofemoral venous outflow obstruction.