30-year-old male who presented with urinary retention and gradually worsening bilateral lower limb weakness, but this was missed. Initially treated as urinary infection, subsequent visits earned him a Magnetic resonance Imaging (MRI) that revealed T2 hyper intensity and low-lying cerebellar tonsils. Further evaluation by consultant revealed discordant findings to Chiari malformation. Subsequent investigation led to the diagnosis of Neurosyphilis. Importance of senior input, understanding of disease complex, lateral thinking, multidisciplinary involvement and prompt intervention prove central to the management of this patient whom otherwise may have been treated dangerously and inappropriately as symptomatic Chiari malformation.