Cerebral venous thrombosis (CVT) is a rare type of stroke, with a complex clinical presentation that can make it a diagnostic challenge for the swift initiation of anticoagulation. When a hemorrhagic transformation is added, therapeutic management becomes even more complex. We describe a series of four cases, aged between 23 and 37 years old, with cerebral venous thrombosis. They were admitted to our clinic between 2014 and 2022. All cases presented significant challenges in either diagnostic, therapeutic or etiologic evaluation, at different stages of the disease. Late complications such as epilepsy or depression and other behavioral disorders represent long-term sequelae for the patient. Therefore, through its late complications, CVT is not only an acute disease but a chronic disorder with long-term follow-up requirements. The first case of the series is of a postpartum woman with focal neurological deficit caused by CVT with hemorrhagic transformation that presented multiple thrombotic complications and severe depression. The second case is of a man with extensive cerebral thrombosis who developed bilateral papillary edema under therapeutic anticoagulation treatment. The third case is of a woman with bilateral cavernous sinus thrombosis who later developed depressive disorder and focal seizures. The fourth case is of a pregnant woman in the first trimester presenting with a steep decline in consciousness level secondary to deep cerebral vein thrombosis requiring intensive care and subsequently developing a memory disorder. For a long period of time, due to being underdiagnosed, few things were known about CVT. Nowadays, we have all the tools to diagnose, treat, and follow up cases of CVT.