Antimelanoma differentiation-associated gene 5 (MDA5) dermatomyositis (DM) is a subtype of DM associated with characteristic mucocutaneous features. These individuals have an increased risk of developing interstitial lung disease (ILD) that ultimately leads to a complicated clinical course. Certain clinical findings suggest anti-MDA5 positive DM over anti-MDA5 negative DM, including cutaneous ulcers, diffuse nonscarring alopecia, and panniculitis. ILD and pneumomediastinum are known to be two of the most important pulmonary complications of anti-MDA5 DM because of the possibility of a rapidly progressive course and poor survival. This case outlines the unique presentation of pneumomediastinum, subcutaneous emphysema, and ILD in a patient with anti-MDA5 positive DM.