ABSTRACT Background Ureteropelvic junction (UPJ) obstruction is the leading cause of pediatric hydronephrosis. While open pyeloplasty is highly effective, a small proportion of children experience recurrent ureteropelvic junction obstruction (UPJO) necessitating repeat intervention. We aimed to identify potential risk factors for pyeloplasty failure. Methods We prospectively followed 126 children undergoing open Anderson-Hynes pyeloplasty between 2019 and 2021. Demographic, clinical, anatomical, procedural, and postoperative variables were recorded. Patients were monitored for recurrence, defined as worsening hydronephrosis and/or symptoms with diuretic renogram confirmation. Univariate and multivariate analysis identified factors associated with recurrence. Results Median age at pyeloplasty was 17 months, left side was affected in 58% and 73.8% were male. At mean 28.8 months follow-up, UPJO recurred in 9 patients (7%). The only factor significantly associated with recurrence was prolonged postoperative urinary drain leakage, specifically recurrence occurred in 50% (3/6) of cases with prolonged leakage versus 5% (6/120) without (p = 0.005). Conclusions Open pediatric pyeloplasty has a high success rate, yet a minority of patients will experience recurrence necessitating re-intervention. Prolonged urine leakage was the sole predictor of failed repair in our cohort, likely due to inflammation and perianastomotic scarring. Meticulous surgical technique and prompt leak management are vital to optimize pyeloplasty outcomes. Children at higher risk warrant close monitoring to enable early detection and renal salvage.