Acute appendicitis is one of the most common surgical conditions that are diagnosed in children presenting with acute abdominal pain in the emergency department. An atypical presentation of symptoms is encountered in 30% of cases. Atypical localization of the appendix as in left sided appendicitis, although rare, has an increased risk of missed or delayed diagnosis. We present two consecutive cases of left sided appendicitis in order to describe how increased awareness in the second case helped us to avoid pitfalls in the management and diagnosis of this atypical and variant condition. Increased cautiousness and awareness of left sided appendicitis can assist emergency physicians to avoid pitfalls in the management and diagnosis of this atypical and variant condition.