Cryptococcal meningitis is uncommon in pregnant HIV-infected women. The clinical care of an HIV-1 positive pregnant woman with cryptococcal meningitis whose pathology has been previously reported is reviewed to highlight the treatment of the disease and some of the challenges associated with antifungal therapy during pregnancy, including the teratogenicity of antifungal agents, their variable pharmacokinetics in pregnancy, the lack of well-defined treatment duration for such infections, and host factors including compliance. This patient's disease relapsed due to nonadherence after an initial course of intravenous amphotericin. Subsequently, she was successfully treated, with a favorable fetal outcome, with another 2 weeks of amphotericin B, followed by consolidation and maintenance with fluconazole and antiretroviral treatment. This case highlights and reviews the complexities of the management of cryptococcal meningitis in HIV-infected pregnant women.