In this report, we present a complicated case of community-acquired pneumonia in a 5-year-old boy. The patient first presented to the pulmonology clinic with the diagnosis of asthma and a recent history of recurrent pneumonia. Poor compliance to two courses of outpatient oral antibiotics resulted in persistent pneumonia symptoms with unresolved radiographic findings warranting parenteral antibiotics. Despite 2 symptom-free weeks, the patient returned to the emergency department with recurrence of symptoms where imaging revealed a cavitary lesion requiring a prolonged course of parenteral antibiotics. This report further supports the detrimental impact of partially treated infections related to poor compliance to antibiotic regimens.