Superficial vein thrombosis, which is mostly caused by lower extremity varicose vein disease, can be complicated by pulmonary embolism. At the same time, the optimal duration of anticoagulant therapy for pulmonary embolism originated from varicose vein thrombosis is still under debate. On the one hand, the presence of varicose veins is considered a small risk factor for the development of venous thromboembolic events, which persistence determines an increased risk of relapse and requires prolonged anticoagulant therapy. On the other hand, elimination of varicose veins is associated with reduced risk of subsequent venous thromboembolic events. The article describes a clinical case of recurrent pulmonary embolism after surgical treatment of varicose vein disease, which caused primary pulmonary embolism. A 45-year-old patient suffering from left lower extremity varicose vein disease for 5 years was admitted to the intensive care unit with suspected pulmonary embolism. The further examination revealed signs of thrombotic occlusion of the segmental and subsegmental branches of the pulmonary arteries bilaterally and the middle lobe branch of the right pulmonary artery, as well as signs of the right-sided heart overload. In this case, pulmonary embolism was found to originate from thrombosis of the trunk of the great saphenous vein ofthe left lower extremity with a proximal border at the level of the lower leg. No signs of deep vein involvement were detected. The parenteral anticoagulant therapy initiated in the hospital was followed by switching to therapeutic doses of rivaroxaban. The signs of recanalization of involved veins were identified after 6 months of treatment, and it was decided to perform endovenous laser coagulation of the trunk of the great saphenous vein combined with mini-phlebectomy of varicose tributaries on continuous oral anticoagulant therapy. The rivaroxaban therapy was completed a month after intervention. However, 7 days later the patient was diagnosed with repeated symptomatic pulmonary embolism, which originated from thrombosis of the left popliteal vein. It was recommended to resume anticoagulant therapy of indefinite duration. The article discusses the issues of optimal duration of treatment for pulmonary embolism originated from thrombosis of superficial varicose veins, as well as the possible timing of completion of anticoagulant therapy after the intervention.