In the last decades, it has been considered that syphilis and its complications, including neurological damage, are able to be kept under control with proper epidemiological management. However, socio-economic changes and the problem of antibiotic resistance have brought it back into the focus of clinicians. The present study reports on the cases of three male patients of different ages (28, 76 and 51 years) from different social backgrounds and occupations were provided (first patient, nurse; second patient, pensioner; third patient, navigator); they were confirmed to have neurosyphilis, clinically, paraclinically and by imaging. The complications that may occur in the evolution of the disease but also the beneficial effects of targeted, antisyphilitic and symptomatic therapy were outlined. The purpose of the present study was to highlight issues of major importance regarding neurosyphilis, particularly for neurologists, for whom diagnosis may be challenging. It is key for the neurologist to understand the clinical manifestations and limitations of current diagnostic tests. It is important to consider that a positive rapid plasma reagin test result without confirmation of the presence of Treponema pallidum antibodies in the cerebrospinal fluid may represent a false-positive screening test.