Gastrointestinal (GI) involvement by multiple myeloma is a rare entity. Clinical manifestations depend on the site and extent of involvement. GI bleeding, obstruction, and perforation can complicate the disease course. We report a rare case of an extramedullary plasmacytoma ulcerating through the gastric mucosa and presenting as a massive upper GI bleed, which was controlled surgically with en-bloc resection of the mass infiltrating the stomach, distal pancreas, and spleen. To our knowledge, this is the first case of immunoglobulin A (IgA) myeloma with multiple GI organ involvement presenting with massive upper GI bleeding.