An 85-year-old ex-smoker being managed conservatively over 2 years for a small right apical pneumothorax presented to the respiratory clinic with suddenly worsening shortness of breath and chest pain. A chest radiograph demonstrated sudden deterioration in the size of his pneumothorax. Previous CT scans had found emphysematous cystic changes within the lungs, and his new presentation warranted definitive surgical intervention with a right bullectomy and talc pleurodesis through a video-assisted thoracoscopic surgery procedure. The patient made a good recovery and was discharged from clinic a year later. This case demonstrates the importance of follow-up in patients with unresolved pneumothoraces due to the potential for sudden deterioration, and highlights the significance of respecting patient involvement and autonomy in the decision-making process.