A jejunal gastrointestinal stromal tumor (GIST) is a rare neoplasm of the gastrointestinal (GI) tract. Massive bleeding due to a jejunal GIST is a diagnostic and therapeutic challenge. It may be a life-threatening GIST complication that requires urgent intervention. Acute GI bleeding, which requires urgent surgical intervention, is a very rare clinical manifestation of GIST. A jejunal GIST with massive hemorrhage with coronavirus disease 2019 in a male patient in older age with many comorbidities has been not reported in the worldwide literature.