Abstract Introduction Duplex appendix, a rare anatomical anomaly is often encountered incidentally during appendicectomy procedures. It is characterised by the presence of two appendiceal lumens and can be classified using the Cave-Wallbridge classification system. Case An 18-year-old male presents to the Emergency Department with a two-day history of migratory right iliac fossa pain. He was consented and booked for a laparoscopic appendicectomy based on clinical suspicion of acute appendicitis. Intra-operatively, an unexpected finding surfaces—a second pendunculated mass adjacent to the inflamed appendix. Employing laparoscopic linear staples, both the appendix and the adjacent mass were divided. One day post-discharge, the patient presents with severe abdominal pain and computed tomography imaging suggests an intra-abdominal leak. The patient underwent an emergency laparotomy and ileo-caecal resection overnight. Histology revealed the second pedunculated mass was indeed a second appendix, a phenomenon with a reported incidence of 0.004 to 0.009%. Discussion Addressing the nuances of using imaging modalities in the diagnosis and operative planning of acute appendicitis, our discussion raises pertinent questions regarding the necessity of definitive pre-operative imaging in suspected cases. Considering potential pitfalls of incorrect clinical diagnoses; the presence of anatomical anomalies; and other factors influencing surgical decision-making; we scrutinise the proposition of pre-operative imaging protocols in suspected acute appendicitis. Conclusively our case encapsulates the diagnostic and therapeutic conundrums posed by duplex appendix instances, prompting a deeper exploration into the use of imaging techniques in a traditionally clinically diagnosed presentation and the implications thereof in surgical management.