Thrombophlebitis is an inflammatory process in the superficial veins with coexistent vein thrombosis, usually occurring in patients with specific preconditions (trauma, surgery or inactivity, signs of venous insufficiency, malignancies). The concept of thrombophlebitis has evolved over time, and also its definition has changed from thrombophlebitis to superficial vein thrombosis (SVT). SVT course is usually benign, if appropriate and prompt treatment is undertaken. Pharmacologic treatment includes anticoagulation with low‑molecular‑weight heparin, fondaparinux and, more recently, rivaroxaban. In selected cases, the course of thrombophlebitis is not self‑limited, and its management is challenging for clinicians and varies in different centers. SVT complications include deep vein thrombosis, pulmonary embolism, and thrombosis recurrence. In this review, we define nonstandard SVT as the cases presenting with 1 or more of the following features: SVT involving healthy veins; recurrent, migrant, or significantly extended SVT; SVT involving deep vein confluence; or SVT not associated with recognized risk factors, especially if occurring in young individuals. In such nonstandard cases, SVT may also represent the epiphenomenon of a more complex systemic condition. Therefore, investigation may require more attention and resources. This series of clinical cases focuses on uncertainties in the management of nonstandard SVT, from diagnosis to treatment, and it underlines, on the one side, the need of a multidisciplinary approach to investigation and care, and on the other side, the opportunity of a systematic data collection and analysis to provide more reliable recommendations in this setting.