Recurrent venous thromboembolism carries significant risks of morbidity and mortality. Although recurrence can be prevented by ongoing anticoagulant therapy, treatment is inconvenient and associated with risks of major bleeding. As a consequence, the decision as to whether or not to continue anticoagulants after the first three months of treatment must take into account both potential benefits and potential risks. For patients who have developed unprovoked venous thromboembolism, these are often closely balanced and the optimal duration of anticoagulant therapy remains controversial. Recent publications suggest that D-dimer testing may be helpful in stratifying these individuals into higher and lower risks groups for recurrence after anticoagulant discontinuation. This paper reviews recent data surrounding the use of D-dimer to predict the risk of recurrent venous thromboembolism and how this test may help streamline decisions regarding duration of therapy.