Pneumoconiosis is associated with coal dust particles depositing within the lung causing nodules coalesce to form progressive massive fibrosis (PMF). Cavitary lesions can develop in these PMF areas for concerns of tuberculosis and aspergillosis. We present a 59-year-old patient who had coal workers pneumoconiosis and PMF presenting with chronic dyspnea and hemoptysis with an upper cavitary lesion noted on chest imaging. He notes dyspnea with walking very short distances with associated productive cough. He admits to occasional wheezing, paroxysmal dyspnea, hemoptysis, and orthopnea but denies chest pain. He is an everyday smoker. His physical examination was only remarkable for bronchial breath sounds. On review of his prior imaging, he had a right upper lobe infiltrate as far back as 2012. As the years progressed, a new cavitary lesion developed in the PMF area which progressively got larger with a thick wall and no eccentric region noted inside the cavity. Tuberculosis test was negative. He underwent a transbronchial biopsy with methenamine silver stain which showed acute angle branching and septation suggestive of Aspergillus species. He was diagnosed with pulmonary aspergillosis and treated with voriconazole for 1 year. With pneumoconiosis and evidence confirming aspergillosis, the presence of a new lung infiltration with progression into a cavitary lesion leads to a diagnosis of chronic cavitary pulmonary aspergillosis (CCPA). With follow-up imaging showing extensive lung fibrosis, he had chronic fibrosing pulmonary aspergillosis (CFPA), a late-stage manifestation of CCPA.