Community-acquired pneumonia is a leading cause of death from infectious diseases globally. Parapneumonic effusion is one of the most common complications of community-acquired pneumonia. As the infection progresses within the pleural space, loculation and empyema may develop. In rare cases, the parapneumonic effusions can progress significantly within 24 hours, which has been described as explosive pleuritis and may confer additional morbidity. Group A Streptococcus is the leading causative microorganism, which in itself has higher rates of parapneumonic effusions. We describe the case of a 30year-old-female with a past medical history of asthma who presented to the emergency department with a sore throat, cough, and runny nose and was discharged on the same day after treatment of asthma exacerbation with upper respiratory tract infection. She re-presented within 24 hours with shortness of breath and right-sided pleuritic chest pain. Chest x-ray showed a new, large right-sided pleural effusion for which pleural fluid culture grew group A Streptococcus. She ultimately had prolonged hospitalization, requiring chest tube placement, and video-assisted thoracoscopic surgery (VATS). VATS was unsuccessful and she was treated with long-term antibiotics. This case demonstrates the dramatic evolution of explosive pleuritis and highlights the typical challenges encountered in these cases.