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In 2020, an estimated 198,651 patients underwent Bariatric Surgical operations, with Roux-en-Y gastric bypass (RYGB) accounting for 20% of these surgeries. As the prevalence of patients with a history of RYGB increases annually, the importance of lifelong adherence to postoperative recommendations cannot be understated. While RYGB is a remarkably effective procedure, the lifelong risk of anemia and micronutrient deficiencies should be stressed to patients as they are at increased risk due to their altered anatomy. In similar manner, the altered anatomy of exposed jejunum to gastric acid, lends potential for marginal ulcer formation with associated bleeding. Risk for iron deficiency anemia alone is raised as the area of maximal absorption is bypassed. Here we present a case of a 56 year old female with a history of RYGB 13 years prior who presented to the emergency department fatigued and was found to be severely anemic with a hemoglobin of 3.2g/dL. She reported no follow up with Bariatric Medicine and/or Surgery, with recent initiation of ibuprofen for back pain. She was transfused 4 units of packed red blood cells and was treated with anti-ulcer therapy. She was taken for upper endoscopy and found to have marginal ulceration. She was discharged home on proton pump inhibitors, sucralfate, and misoprostol with follow up and repeat upper endoscopy scheduled. Ultimately this patient was at high risk for clinical deterioration due to severe anemia. She responded well to nonoperative management, emphasizing the importance of lifelong adherence to postoperative recommendations.