Primary lung cancer rarely presents with pneumothorax, and when it does one needs to consider endobronchial obstruction as a possible etiology. We present the case of a 31-year-old woman who was diagnosed with asthma within the past 2 years and was recently treated for pneumonia. She presented with persistent massive hydropneumothorax. She had concurrent endobronchial obstruction secondary to adenoid cystic carcinoma. Her pneumothorax decreased with relief of her endobronchial obstruction after interventional bronchoscopy. This case report discusses different types of pneumothoraces and emphasizes that some types are not relieved by chest tube placement, but by relief of endobronchial obstruction. Also emphasized are radiographic findings suggestive of endobronchial obstruction, which should be suspected in an adult with new onset of wheezing with no risk factors and no earlier diagnosis of asthma; this obstruction may be cancerous.