While aspiration pneumonia constitutes the majority of pneumonia cases in the elderly, it remains highly underdiagnosed. We experienced a case of recurrent pneumonia and chronic cough that was later diagnosed as aspiration pneumonia and diffuse aspiration bronchiolitis (DAB) due to recurrent hemorrhaging from an intramedullary cavernous malformation. The patient was finally diagnosed when life-threatening respiratory depression caused emergency attention. This is the first report of hemorrhaging from an intramedullary cavernous malformation diagnosed due to aspiration pneumonia and DAB. These findings highlight the importance of considering aspiration in cases with recurrent pneumonia or chronic chough. The underlying cause may be a life-threatening condition.