Complicated parapneumonic effusions and empyemas are associated with significant morbidity and mortality. When managing a potentially infected pleural space, current guidelines support performing diagnostic thoracentesis prior to consideration of chest tube insertion. We present a case demonstrating our clinical approach to the management of complicated parapneumonic effusions and empyemas, with patient presentation and initial point-of-care thoracic ultrasound assessment guiding consideration of immediate insertion of small-bore (14 F) chest tube.