Acute febrile neutrophilic dermatosis, or Sweet syndrome, is a rare disorder associated with medications, underlying malignancy, or systemic inflammatory conditions. We present the case of a 71-year-old male living with well-controlled human immunodeficiency virus (HIV) on antiretroviral therapy, who presented with multiple painful, pseudo-vesicular, almost-necrotic appearing papules on his bilateral palms in the setting of constitutional symptoms and altered mental status. Biopsy of his palmar lesions revealed a dense, diffuse, dermal neutrophilic infiltrate consistent with Sweet syndrome. Infectious, rheumatologic, and oncologic work-up was negative. He was treated initially with intravenous immunoglobulin, prednisone, and dapsone; and he was continued on suppressive dapsone. He responded well clinically, but he relapsed multiple times in the setting of medication non-adherence before his ultimate diagnosis with sarcoidosis. A review of the literature of persons living with HIV and diagnosed with Sweet syndrome reveals no clear clinical association between the two despite plausible pathologic mechanisms. Patients living with HIV who are diagnosed with Sweet syndrome should be evaluated thoroughly for potential etiologies; the search for the underlying etiology of Sweet syndrome should go beyond their diagnosis of HIV.