Bullous emphysema is a recognized complication of chronic obstructive pulmonary disease (COPD), often leading to pneumothorax. However, intrabullous fluid accumulation is an uncommon manifestation. We present a case of a 55-year-old chronic smoker with a history of pulmonary tuberculosis and COPD, admitted with large hemoptysis. Imaging revealed a massive cystic lesion within an emphysematous bulla. Despite negative infectious and embolic workup, the patient's critical condition precluded surgical intervention. Embolization with interventional radiology yielded good results and controlled bleeding. This case emphasizes the significance of meticulous history-taking, comprehensive imaging review, and a multidisciplinary approach to diagnosis and management in challenging clinical scenarios.