Nearly half of medical errors can be attributed to an error of clinical reasoning or decision making. It is estimated that the correct diagnosis is missed or delayed in between 5% and 14% of acute hospital admissions. Through understanding why and how physicians make these errors, it is hoped that strategies can be developed to decrease the number of these errors. In the present case, a patient presented with dyspnea, gastrointestinal symptoms and weight loss; the diagnosis was initially missed when the treating physicians took mental short cuts and used heuristics as in this case. Heuristics have an inherent bias that can lead to faulty reasoning or conclusions, especially in complex or difficult cases. Affective bias, which is the overinvolvement of emotion in clinical decision making, limited the available information for diagnosis because of the hesitancy to acquire a full history and perform a complete physical examination in this patient. Zebra retreat, another type of bias, is when a rare diagnosis figures prominently on the differential diagnosis but the physician retreats for various reasons. Zebra retreat also factored in the delayed diagnosis. Through the description of these clinical reasoning errors in an actual case, it is hoped that future errors can be prevented or inspiration for additional research in this area will develop.