Patients with chronic obstructive pulmonary disease (COPD) are at an increased risk for numerous pulmonary complications, including secondary spontaneous pneumothorax (SSP) and lung herniation. We describe the case of a 66-year-old female patient with severe COPD and previous lingula-sparing left upper lobectomy from adenocarcinoma who presented to the emergency department with a painful anterior chest wall mass that varied in size with respiration. This finding, in a patient with a prior history of an invasive thoracic procedure, is suggestive of lung herniation. Further investigation revealed an SSP mimicking the classic physical exam finding of a lung herniation. The patient was deemed a poor surgical candidate; therefore, talc pleurodesis was administered with resolution of the pneumothorax.