Objective To determine the potential predictors of antegrade ureteral stenting (AUS) failure in patients with malignant and benign ureteral obstruction. Method We retrospectively evaluated 116 AUS procedures performed in 80 patients for ureteral obstruction due to malignant and benign causes. Variables such as etiology for obstruction, ureter shape, previous treatment regimen, history of ileal loop diversion, and presence of percutaneous nephrostomy were recorded. Univariate and multivariate logistic regression methods were used between these variables and stent failure. Results Antegrade ureteral stenting was performed as single stage in 24 procedures (n: 24/116, 21%) and performed as a two-step approach after percutaneous nephrostomy in 92 procedures (n: 92/116, 79%). Ureteral stent was successfully deployed in 112 AUS procedures (n: 112/116, 96.5%). In 35 of these successful procedures, the patients were referred to our department due to prior failed retrograde ureteral stenting (RUS). Subsequent stent failure occurred in 40 procedures after a median interval of 39 days. Pre-stenting percutaneous nephrostomy (PN) was a statistically significant risk factor for stent failure (p: 0.041), and age showed an inverse relationship with stent failure (p: 0.008). Complications in early (within the first 30 days after procedure) and late stage occurred in a total of 17 procedures. Early complications included urinary tract infection (n: 11), stent migration (n: 3), and malposition (n: 1). Late complications (after 30 days) were urinary tract infection (n: 1) and stent migration (n: 1). Conclusion This study suggests that AUS can be performed effectively in both benign and malignant ureteral obstructions including cases with prior failed RUS. Two-step AUS after percutaneous nephrostomy was found to be a significant risk factor for subsequent stent failure in our study cohort.