Numerous controversies exist in the diagnosis of venous thromboembolism despite all the guidelines that are currently available. Screening of malignancy in venous thromboembolism has been a debated issue, as it has not been shown to change mortality. Calf vein thrombosis is also a controversial topic, but evidence points to risk stratifying those patients. Overdiagnosis, most notably from the finding of subsegmental pulmonary embolism, ultimately requires evaluating the risk and benefit for each patient. In addition, treatment of upper extremity deep vein thrombosis is a challenging scenario that is quite common in clinical practice. Finally, postthrombotic syndrome may be reduced by graduated compression stockings, but their use has not been validated for preventive use at this time and is still being discussed.