An unusually high surgical site infection (SSI) rate after Roux-en-Y gastric bypass (RYGB) was noted on routine outcomes review. Surgeon A, who had a rate of 8.9%, utilized the transoral technique (passage down esophagus into gastric pouch) for anvil insertion for the circular-stapled gastrojejunostomy. By comparison, SSI rate was 0% for Surgeon B, who inserted anvil transabdominally (direct passage into stomach via gastrotomy) and used wound protection (wound protector and plastic drape over stapler). We sought to determine if it was the technique for anvil insertion (transoral or transabdominal) or use of wound protection that could help reduce SSIs. In mid-2017, Surgeon A added wound protection (wound protector and plastic drape over stapler) to the transoral technique to minimize oral flora wound contamination. Surgeon B made no changes. In this study, wound-related outcomes are examined, comparing patients who underwent surgery before (Group 1) versus after (Group 2) this intervention. Statistical analysis performed utilizing t tests and Chi square analysis; p < 0.05 considered significant. Three hundred and thirty-three patients underwent RYGB. Group 1 consisted of 182 patients over 17months; 151 patients over 13months were in Group 2. Groups were similar in age, BMI, gender, and prevalence of diabetes. There was a decrease in SSIs between Group 1 and Group 2 (5 vs. 0, p = 0.04). 11 wound complications occurred in Group 1 (5 SSIs, 4 seromas and 2 hematomas); whereas 2 wound complications occurred in Group 2 (1 seroma and 1 hematoma); decrease from 6 to 1.3%, p = 0.03. This study demonstrates that changing technique can lead to best outcomes. There was a dramatic reduction of wound complications and complete elimination of SSIs with a change in operative technique. The higher risk of SSI with the transoral anvil insertion when preforming a circular-stapled anastomosis can be mitigated with use of wound protection.