A pleural effusion is an accumulation of fluid in the pleural space due to an imbalance between formation and removal. They're commonly caused by heart failure or infections. We report a case of a 56-year-old male with community-acquired pneumonia and a trace pleural effusion on presentation. Despite clinical improvement with antibiotic therapy, the effusion significantly increased on day two. This case report is unique because the patient had an enlarging effusion, but remained asymptomatic and denied worsening shortness of breath, chest pain, or cough. The patient was treated successfully with chest tube placement and intrapleural fibrinolytic therapy. This report emphasizes the importance of repeat imaging for asymptomatic parapneumonic effusions (PPE) that can complicate community-acquired pneumonia. We aim to raise awareness of the atypical presentation and management of parapneumonic effusions through a case report.