Intussusception is an uncommon but serious complication following Roux-en-Y gastric bypass (RYGB), historically occurring in 0.4–3.9% of postoperative patients. Amid rising GLP-1 receptor agonist prescribing, this case series describes six RYGB patients presenting with intussusception while actively or recently using GLP-1 therapy. Presentations typically involved acute abdominal pain, with imaging frequently demonstrating jejunojejunal intussusception near the anastomosis. Most cases required laparoscopic exploration, while one involved ischemic bowel requiring resection. A broader Dartmouth Health–wide analysis from 2017–2025 revealed no significant temporal association between GLP-1 prescribing and intussusception rates, suggesting isolated clustering rather than a system-level trend. These findings contextualize concern regarding GLP-1–related bowel complications and underscore the need for continued surveillance as GLP-1 use expands.