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Despite the significant reduction in overall mortality among individuals with HIV in the era of combination antiretroviral therapy (cART), chronic HIV infection remains associated with a broad spectrum of neurocognitive disorders. This correlation is attributed to the pronounced neurotropism of the virus, which infects the central nervous system (CNS) from the early stages of primary infection. However, other contributing factors include comorbidities, accelerated ageing, various forms of dementia, psychiatric disorders, and CNS viral escape. The latter, characterized by detectable levels of HIV-RNA in cerebrospinal fluid despite undetectable or lower levels in plasma, poses a significant challenge in HIV management. We herein describe the case of a man with HIV infection whose adherence to therapy was suboptimal. The patient presented to medical attention with cognitive impairment, ultimately attributed to a case of viral escape. Management was particularly challenging due to the necessity of selecting a cART regimen with enhanced CSF penetration, given his history of multiple virologic failures, previously detected resistance-associated mutations, and poor treatment compliance.