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Highlights • Intestinal malrotation is a congenital rotational anomaly that occurs as a result of an arrest of normal rotation of the embryonic gut, said to occur in 1 in 6000 live births. Once thought to be a disease of infancy, is now more prevalent in older ages. • Cases of left sided appendicitis with previously undiagnosed intestinal malrotation therefore becomes more challenging to diagnose, and often time’s definitive surgical management is delayed. A varied list of differential diagnosis needs to be considered. • This case presentation shows the difficulties encountered and the variation in presentation that lead us down a different path prior to attaining a formal diagnosis. • CT abdomen was required to confirm the diagnosis, and in a paediatric age group, radiation exposure is always weighed upon risk-benefit ratio. • Definitive management is surgical intervention., Introduction Intestinal malrotation is a congenital rotational anomaly that occurs as a result of an arrest of normal rotation of the embryonic gut, said to occur in 1 in 6000 live births. Due to the abnormal caecal and appendix position, diagnosis of acute appendicitis becomes more challenging, thus leading to diagnostic and operative intervention delays. Our aim is to highlight the diagnostic challenges in this clinical scenario. Presentation of case We present a case of a 10 year old boy with previously undiagnosed intestinal malrotation with a left sided acute appendicitis. Initial symptoms lead to a treatment for gastroenteritis, however, due to ongoing pain a CT abdomen was done which showed the malrotation and appendicitis. He required a laparoscopy converted to open appendicectomy due to an appendicecal mass. Discussion Historically, intestinal malrotation was thought to be a disease of infancy with infrequent occurrence after the age of one year. However, recent analysis has shown an increase in presentations after one year of life into adulthood. Thus, the prevalence of malrotation in children and adults over the age of one year appear to be higher than initially presumed. Conclusion Left sided acute appendicitis is a diagnostic dilemma, thus often leading to management delays. It is pertinent to remember that malrotation of the gut is more common than previously thought, and not just a disease of infancy. It is advisable to consider imaging studies while balancing the risk-benefit-ratio of radiation exposure, especially in paediatric cases to cinch the diagnosis.