Pulmonary thromboembolism and exacerbation of chronic obstructive pulmonary disease are common conditions. Chronic obstructive pulmonary disease is a clinical risk factor for pulmonary thromboembolism. The presentation of acute pulmonary thromboembolism and acute exacerbation of chronic obstructive pulmonary disease often mimic each other so closely that they cannot be distinguished clinically. The structural abnormalities of the lungs in chronic obstructive pulmonary disease make also difficult to interpret the results of noninvasive tests like ventilation-perfusion lung scans. Therefore, diagnosing acute pulmonary thromboembolism in patients with underlying chronic obstructive pulmonary disease is a challenging task. In order to update knowledge of the subject and offer suggestions regarding conduct, we evaluated various studies addressing this theme, including case reports and case series. In addition, we reviewed diagnostic approaches to acute pulmonary thromboembolism, and we reflect upon that topic. The clinical probability of pulmonary thromboembolism concomitant to chronic obstructive pulmonary disease is typically intermediate, as is positivity on the ventilation-perfusion lung scan. Diagnostic algorithms should take that into consideration.