A 26-year-old smoker male presented with a history of sudden onset dyspnea and right-sided chest pain. Chest radiograph revealed large right-sided pneumothorax which was managed with tube thoracostomy. High-resolution computed tomography thorax revealed multiple lung cysts, and for a definite diagnosis, a video-assisted thoracoscopic surgery-guided lung biopsy was performed followed by pleurodesis. This clinicopathologic conference discusses the clinical and radiological differential diagnoses, utility of lung biopsy, and management options for patients with such a clinical presentation.