Roux-en-Y gastric bypass (RYGB) is one of the most common bariatric surgeries performed and has aided many people with their weight loss efforts. However, manipulating the gastrointestinal anatomy may have numerous consequences. Various complications of RYGB can occur during the early to late post-op periods, and abdominal pain is the most common symptom reported. The etiologies that present as abdominal pain are heterogeneous in anatomical origin, onset, severity, and management; therefore, differentiating diagnoses is crucial. The physical exam, inciting triggers, and alleviating factors can direct diagnostic measures accordingly. Prompt recognition and identification of these patients' underlying causes of abdominal pain are vital for accurate diagnosis and treatment. Methods can range from conservative management to surgical intervention, depending on the severity of the complication. In this report, we recount the cases of two patients who underwent elective RYGB and presented to the emergency department (ED) months later with abdominal pain. After the labs were taken and diagnostic tests were conducted, it was discovered that both patients had multiple underlying factors that could have contributed to their pain. This study aims to describe the diverse etiologies of abdominal pain encountered in these bariatric patients and explore the appropriate management strategies utilized for each case.