Stump appendicitis, a rare postoperative complication of appendicectomy, is inflammation of the remnant appendix tissue due to incomplete removal of the appendix at the index operation. Due to a past surgical history of appendicectomy, there is often a diagnostic delay. This delay can result in increased morbidity and mortality for patients. This series seeks to describe two cases encountered in a London district general hospital to elucidate the diagnostic, management, and operative challenges of stump appendicitis. Our case series demonstrates the importance of recognition of stump appendicitis as a differential for patients presenting with abdominal pain and previous appendicectomy. Active exclusion of this differential diagnosis in a patient with previous appendicectomy who presents with right iliac fossa pain is vital. Early identification and treatment can prevent morbidity in the patient population. We highlight that complete operative documentation and access to medical records are useful for this diagnosis.