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Type 2 diabetes mellitus is a major health burden globally, with increasing use of glucagon-like peptide-1 receptor agonists (GLP-1RAs) such as semaglutide for glycemic control and cardiovascular risk reduction. While generally well tolerated, GLP-1RAs have been associated with gastrointestinal side effects, including rare reports of bowel obstruction. We describe a case of a 39-year-old male with type 2 diabetes who presented with nausea, vomiting, and abdominal pain five weeks after starting semaglutide. He had four weekly subcutaneous doses of semaglutide 0.25 mg, followed by one dose of 0.5 mg on the fifth week. Examination demonstrated a tender, distended abdomen. Imaging revealed small bowel pseudo-obstruction accompanied by ileitis, with no mechanical cause identified. A diagnosis of bowel pseudo-obstruction was made after exclusion of other causes, including infection, inflammatory bowel disease, and mechanical obstruction. The patient improved with conservative management following drug cessation. Patient education and regular monitoring are crucial, especially for those reporting persistent abdominal symptoms while taking a GLP-1RA for the control of diabetes or weight loss.