Glucagon-like peptide-1 receptor agonists (GLP-1 RAs) are commonly used for managing type 2 diabetes and obesity. These drugs improve glycemic control and promote weight loss, but they can cause gastrointestinal side effects such as gastroparesis and bowel obstruction, particularly in patients with preexisting GI motility issues. A 55-year-old woman with obesity, type 2 diabetes, and a history of small bowel obstruction developed severe abdominal pain and nausea after starting semaglutide. She was diagnosed with small bowel obstruction and treated with nasogastric decompression and bowel rest. Her condition resolved, but the potential risks of continuing GLP-1 RA therapy were reassessed. GLP-1 RAs reduce gut motility by slowing gastric emptying and altering the migrating motor complex (MMC), increasing the risk of conditions like gastroparesis and bowel obstruction. The patient's prior GI issues and GLP-1 therapy likely contributed to her obstruction. GLP-1 RAs have been linked to bowel obstruction, particularly in those with prior GI motility problems. Clinicians should monitor for symptoms in such patients and weigh the benefits of improved glycemic control against the risk of GI complications. In some cases, discontinuing GLP-1 RA therapy may be appropriate. This case highlights the need for caution when prescribing GLP-1 RAs to patients with a history of gastrointestinal issues. Personalized treatment approaches are essential to balance therapeutic benefits with risks. Further research is needed to understand the mechanisms of GLP-1 RA-induced bowel obstruction.