Semaglutide, a glucagon-like peptide-1 (GLP-1) receptor agonist increasingly prescribed for weight loss, is generally well tolerated but may have underrecognized gastrointestinal complications. We present the case of a 59-year-old woman with an extensive abdominal surgical history who developed small bowel obstruction (SBO) shortly after semaglutide administration. Given semaglutide's effects on gastric motility and its rising use, this case highlights the importance of caution when prescribing GLP-1 agonists to patients with a history of intra-abdominal surgeries and intra-abdominal adhesions.