The use of D-dimer assay to screen for aortic dissection has become routine in clinical practice. Although an uncommon disease entity, aortic dissection is rapidly fatal without prompt diagnosis, and biochemical detection in the proper clinical context is crucial. We performed a retrospective chart review of all aortic dissections presenting to a community tertiary care center between 2000 and 2016 and identified three patients in whom laboratory D-dimer testing was positive and a diagnosis of Stanford Type A aortic dissection was confirmed with computed tomography angiography based on clinical assessment and a newly validated risk stratification tool.