Introduction: Spontaneous hemothorax is a rare condition known to be associated with anticoagulation. We describe a case of fatal hemothorax associated with 2 different fungi that presented a therapeutic dilemma. Description: A 74-year-old female with past medical history significant for hyperhomocysteinemia secondary to MTHFR gene mutation, bioprosthetic aortic valve replacement, deep venous thrombosis, pulmonary embolism and paroxysmal atrial fibrillation on therapeutic anticoagulation presented with fever, dyspnea and hemoptysis. CT of the chest showed an actively extravasating left lung hematoma extending into the pleural space with moderate hemothorax and a small focus of gas within the collection and underlying multifocal pneumonia. Systemic anticoagulation was held and she received antibiotics for pneumonia despite which hypoxia worsened and she was intubated. She required pressors secondary to septic shock. She underwent multiple bronchoscopies and chest tube placement despite which she continued to have recurrent hemothorax suspected secondary to an actively hemorrhagic lung abscess. While in the operating room for video-assisted thoracoscopic surgery (VATS) she suffered cardiac arrest with return of spontaneous circulation in 2 minutes that resulted in multiorgan dysfunction. VATS was aborted. Cultures from previous bronchoscopy resulted in growth of Penicillium and Aspergillus species and she was started on antifungal therapy. However, she subsequently developed multiple pulmonary emboli and embolic brain infarcts. In light of clinical deterioration and grim prognosis, the family opted for comfort measures. Discussion: Despite its association with hemoptysis, there are limited studies describing the occurrence of massive spontaneous hemothorax in aspergillosis. Our case is made additionally interesting by the co-infection with Aspergillus and Penicillium species simultaneously. The patient’s hyperhomocysteinemia predisposes her to a prothrombotic state, compounded by atrial fibrillation that was likely the cause of multiple embolic infarcts in paradox to her actively hemorrhagic abscess that precluded systemic anticoagulation. The therapeutic dilemma and rapid clinical deterioration raise the need for further investigation into the condition to augment early diagnosis and intervention.