Gastrointestinal stromal tumors (GISTs) are neoplasms that arise from the wall of the gastrointestinal tract or, rarely, from other intra-abdominal tissues. They are the most common mesenchymal tumors of the gastrointestinal tract and they should be considered in the differential diagnosis of obscure gastrointestinal bleeding. Computed tomography angiogram (CTA) can be utilized as an alternative imaging study when endoscopic and colonoscopy results are non-diagnostic. We report a case of a 59-year-old woman who presented with recurrent episodes of obscure overt gastrointestinal bleeding secondary to a gastrointestinal stromal tumor (GIST).