Vanishing lung syndrome (VLS) is also referred to as idiopathic giant bullous emphysema and is a rare manifestation of chronic obstructive pulmonary disease (COPD). Middle-aged tobacco smokers, younger marijuana users, and those with alpha-1-antitrypsin deficiency may especially be affected. The clinical and radiographic findings of VLS may initially be misinterpreted as spontaneous pneumothorax. High-resolution CT is the diagnostic imaging modality of choice in these patients and can help to differentiate VLS from pneumothorax. Such imaging also helps guide appropriate management. Management of VLS ranges from a conservative to a surgical approach depending upon patients' comorbidities and candidacy for surgical resection. We present a case of a 64-year-old man with frequent hospitalizations for COPD exacerbation admitted with worsening shortness of breath and was found to have giant bullae mimicking a pneumothorax on the initial presentation.