Proximal hypospadias repair remains challenging. Our approach to the first stage of two-stage proximal hypospadias repairs has evolved from using Byars' flaps to preputial inlay grafts in anatomically suitable cases and pedicled preputial flaps in more complex repairs. We reviewed our outcomes, hypothesizing that inlay grafts and pedicled preputial flaps were associated with lower complication risks than Byars’ flaps. A single institution, retrospective, cohort study of consecutive two-stage, primary, proximal hypospadias repairs performed from 2007 to 2017 was conducted. Patients with <6 months follow-up and incomplete operative reports were excluded. Risk of complications (fistula, dehiscence, diverticulum, meatal stenosis, stricture) were evaluated following urethroplasty and stratified by first-stage repair technique. As technique refinements have been made since 2012, comparisons between two temporal subgroups (those who underwent repair in 2007–2012 and in 2013–2017) were made. 78 of 127 patients met inclusion criteria. Overall complication rate was 47% (Summary Table). Median follow-up was 25.4 months (range 6.4–128.5 months) after urethroplasty. Pedicled preputial flaps (hazards ratio HR 0.30; 95% Confidence Interval CI 0.14–0.65) and inlay grafts (HR 0.32; 95% CI 0.11–0.95) were associated with lower complication risks compared to Byars' flaps (Summary Table). Median time to complication was significantly shorter for Byars’ flaps (5.7 months) than for inlay grafts (40.6 months) and pedicled preputial flaps (79.2 months) by Kaplan Meier analysis. Temporal subgroup comparisons showed that overall complication rates decreased from 70% to 31% (p = 0.001), but differences in complication rates by first-stage technique were not statistically significant. In our cohort, repairs with Byars' flaps had the highest complication rate, which is consistent with our observations that urethras tubularized from Byars’ flaps lack appropriate backing and are hypermobile and irregular. To overcome these shortcomings, modifications were made to our approach to two-stage proximal hypospadias repairs with the use of inlay grafts and pedicled preputial flaps quilted to the underlying corporal bodies to optimize the stability of the urethral plate. Our preliminary results are promising. Approach to the first stage of two-stage repairs affects outcomes. Pedicled preputial flaps and inlay grafts were associated with lower complication risks than Byars’ flaps. Refinement of technique and patient selection may have resulted in fewer complications in the short term. However, long-term follow-up is needed.Summary Table. Overall Complications and Unadjusted Cox Proportional Hazards Model Comparing Complications by First-stage Repair TechniqueOverall ComplicationsAll (N = 78)Inlay Graft (N = 13)Pedicled Preputial Flap (N = 33)Byars' Flaps (N = 21)Combined (N = 11)Complicationsa37 (47%)4 (31%)11 (33%)17 (81%)4 (36%)Median Number of Complications Per Patient0 (0–2)0 (0–2)0 (0–2)1 (0–2)0 (0–1)Type of Complications (n, % of cohort)bFistula18 (23%)2 (15%)6 (18%)8 (38%)2 (18%)Glans/Partial dehiscence10 (13%)1 (8%)06 (29%)3 (30%)Stricture6 (8%)2 (15%)1 (3%)3 (14%)0Diverticulum3 (4%)01 (3%)2 (10%)0Meatal Stenosis3 (4%)03 (9%)00Dehiscence2 (2.5%)01 (3%)1 (5%)0Unadjusted Cox Proportional Hazards Model Comparing Complications by First-stage Repair TechniqueRepairHazard Ratio95% Confidence IntervalsInlay Graft versus Byars' Flaps0.320.11–0.95Pedicled Preputial Flap versus Byars' Flaps0.300.14–0.65Combined versus Byars' Flaps0.480.18–1.31aThis notes the number of patients who developed complications. If a patient developed two complications, they were only counted once for this variable.bThis notes the number of patients with each type of complication.