Transverse myelitis is an uncommon but well-defined neurological syndrome. However, a high index of suspicion is needed to diagnose this condition, especially when it occurs in concomitance with preexisting spinal canal stenosis. We report our patient, a 48 year old male, who initially presented to our spine clinic with acute onset unilateral lower limb weakness associated with urinary retention, which was suspected to be cauda equina syndrome due to a prolapsed intervertebral disc. However, initial magnetic resonance (MR) imaging showed only mild spinal canal stenosis from L2-L5 and C3- C6 levels; thus, the possibility of cauda equina syndrome was ruled out. A few days later, patient developed ipsilateral upper limb weakness giving an impression of hemiparesis due to stroke. However, imaging of brain returned normal. There was still a dilemma whether symptoms could be due to cervical myelopathy as there was mild cervical cord compression with early myelomalacia changes, but the findings were subtle to come to a definite conclusion. Subsequently, patient desaturated and required ventilatory support. Repeat MR imaging of the cervical spine revealed T2 hyperintensities spanning multiple levels in the cervical cord which highlighted the possibility of transverse myelitis and the diagnosis was clinched after a CSF analysis. Despite the debilitating effects, patient responded well to corticosteroid therapy and gradually recovered. This case is reported to highlight the diagnostic dilemma and the rapid progression of transverse myelitis that demands timely medical intervention to avoid permanent disabilities.