Violation of the balance between the production and absorption rate of the cerebrospinal fluid (CSF) might result in hydrocephalus or the spontaneous intracranial hypotension syndrome (SIH), which is usually presented with a unique type of headache. Several hypotheses have been suggested regarding the pathogenesis of this syndrome, including spinal CSF leakage due to located damage to the spinal dura. Another theory suggests increased CSF absorption from the spinal epidural space caused by declined inferior vena cava pressure. SIH is characterized by typical radiological findings, including the presence of subdural collections or hematomas, sagging of the brain parenchyma and the cerebellar tonsils, and brain meninges enhancement. Spinal imaging studies may help in locating the CSF leakage site when it exists. The diagnosis is based on the presence of orthostatic headaches together with typical clinical and imaging characteristics, after the exclusion of any recent medical interventions or other possible etiologies for the presence of SIH. The main treatment includes autologous epidural bloodpatch, even though symptomatic relief may be achieved with supportive or medical treatment alone. The presence of subdural collections or hematomas among patients presenting with orthostatic headaches suggests the need for further clinical and imaging evaluation prior to the surgical drainage, whenever possible. Two patients who were recently treated in our institution are presented, together with a proposed management algorithm.