Background: Meningovascular syphilis, a distinct classification of neurosyphilis, has gained attention for its association with cerebral ischemia, particularly among individuals living with HIV. This unique manifestation of syphilis affects the meningeal and vascular structures of the central nervous system, leading to cerebrovascular complications. In this case report, we present the case of a young man diagnosed with neurosyphilis and HIV after presenting with an ischemic stroke. We discuss the challenges associated with diagnosing neurosyphilis, given its frequent atypical presentations that can mimic other diseases. Furthermore, we explore the management approach for these coexisting conditions. Case Presentation: A right-handed male patient presented with a sudden paresis of the right upper and lower extremities, along with facial deviation to the left, and demonstrated low verbal output, limitation in constructing sentences, and conveying thoughts or ideas effectively. Upon admission, the patient's neurological examination revealed a FOUR coma scale of 16. He exhibited motor aphasia, right facial paralysis sparing the forehead, and right upper and lower extremity spastic hemiparesis with a strength of 3 out of 5 on the Medical Research Council scale. The Plantar reflex was positive on the affected side. Brain magnetic resonance imaging revealed left middle cerebral artery infarction (cortical and lenticulostriate territory acute infarction). Conclusion: This case highlights the need for treating physician to have a high index of suspicion towards meningovascular syphilis as a potential cause of stroke in young individuals. This is crucial, especially when there is also a concurrent HIV infection, as it requires specific treatment.