Parapneumonic effusions occur commonly in patients hospitalised with pneumonia. Both complicated parapneumonic effusions and empyema are often managed initially with tube thoracostomy and intrapleural t-PA and DNase. If complete expansion of the lung is not achieved, surgical intervention is considered. We present three cases of patients with complicated parapneumonic effusions who experienced complete recovery despite declining surgical intervention and discuss the pitfalls in management. While very few patients have complete radiological resolution at the time of discharge, medical therapy is successful in at least 90% of cases. At 3-6 months from presentation, the radiological findings may improve significantly with antibiotic therapy. Surgery should be considered for patients with non-resolving sepsis markers including elevated temperature, C-reactive protein, and white blood cell count, in addition to non-improving imaging. Incomplete resolution of the parapneumonic effusion should not be considered a treatment failure, and attempts to normalise CT imaging may result in prolonged hospitalisation and unnecessary surgical intervention.