We report the case of a 36-year-old woman, a person living with HIV/AIDS (PLHA), who presented with chronic headache, fever, and significant weight loss over three months. Examination revealed pallor and neck stiffness, with no focal neurological deficits. Laboratory investigations showed advanced immunosuppression (CD4 count of 9 cells/µL) and positive autoimmune markers (ANA 2+, anti-Mi2 antibody, anti-Sp100 antibody). CSF studies and clinical evaluation confirmed cryptococcal meningitis. The patient was treated with liposomal amphotericin B and fluconazole following detection of flucytosine resistance with symptomatic improvement in a few weeks. This case highlights the complexity of diagnosing headache in PLHA, the importance of considering cryptococcal meningitis even when classical features are absent, and the challenges of treatment in case of antifungal resistance and resource-limited and immunosuppressed settings.