We report a case of nephropleural fistula causing empyema and respiratory failure in a 68-year-old gentleman with a long history of urological problems including recurrent nephrolithiasis and urinary tract infections. He was admitted with sepsis, a productive cough, pyuria, and reduced breath sounds over the left hemithorax. Radiological imaging revealed a fistulous connection between a left-sided perinephric abscess and the pleural space. He was commenced on broad spectrum intravenous antibiotics but developed progressive respiratory failure requiring intensive care admission. Urinary and pleural aspirates cultured facultative anaerobic pathogens with identical resistance patterns. Drainage of thoracic and perinephric collections was carried out, allowing him to be extubated after 24 hours and discharged home after 18 days on an extended course of oral antibiotics. Left nephrectomy is now planned after a period of convalescence. Empyema developing in patients with known urolithiasis should alert the treating physician to the possibility that a pathological communication has formed especially if typical urinary tract pathogens are cultured from respiratory sampling.