A 63-year-old woman with a history of chronic obstructive pulmonary disease (COPD) presented with several days of a productive cough, shortness of breath, and fever. Based on her clinical history, physical exam, and diagnostic studies, she was diagnosed with community-acquired pneumonia and admitted to the hospital. She was treated with ceftriaxone and doxycycline, intravenous fluids, and supportive care. The patient improved rapidly over 48 hours and was discharged home (she lived with her daughter and grandson) with a prescription for doxycycline (an oral antibiotic) to complete a 7-day course and guaifenesin for a persistent cough.