Postprandial hypoglycemia is a rare complication after Roux-en-Y gastric bypass (RYGB). The underlying pathophysiology remains to be fully understood.We present a case of a 49-year-old woman with a past medical history of mesenteric thrombosis due to prothrombin-related thrombophilia, which culminated in RYGB 10 years prior to presentation. The patient had been given anticoagulation treatment for several years, which she abandoned one year prior to presentation. She presented to our consultation with episodes of postprandial hypoglycemia and severe anemia due to iron and vitamin B12 deficiencies.Dietary adjustments were set in place to prevent hypoglycemia and neuroglycopenic symptoms. Intravenous iron and intramuscular vitamin B12 supplementation led to full recovery of hemoglobin levels, allowing restart of oral anticoagulation to prevent recurrence of thrombotic events.