Background/Objectives: Bariatric surgery is a central cornerstone in obesity treatment. We aimed to assess the impact of diabetes on the postoperative outcomes of bariatric surgery and compare three techniques: sleeve gastrectomy, Roux-en-Y, and gastric banding. Methods: We extracted data from the National Inpatient Sample (2015–2019) using ICD codes. The primary outcome was postoperative mortality. Secondary outcomes were major bleeding, atrial fibrillation, and acute renal failure. Results: Among patients who underwent sleeve gastrectomy, diabetes was associated with a higher adjusted risk of mortality (aOR 2.07 [1.36–3.16]), atrial fibrillation, and acute renal failure, but a similar risk of bleeding. Among patients who underwent Roux-en-Y, diabetes did not increase mortality and bleeding risk. Still, it was associated with a higher risk of atrial fibrillation and acute renal failure. Among patients who underwent gastric banding, diabetes was only associated with a higher risk of bleeding. When comparing the three techniques in diabetes patients, Roux-en-Y was significantly associated with higher mortality and acute renal failure risk when compared to the other procedures. Bleeding was more common in Roux-en-Y than in Sleeve. Conclusions: In total, diabetes is associated with worse postoperative outcomes in bariatric surgery, regardless of the technique. Among diabetes patients, Roux-en-Y was associated with the highest mortality and morbidity.