Kaposi sarcoma is the most common neoplasm associated with Human Immunodeficiency Virus (HIV) infection. Most patients with a confirmed diagnosis experienced limited disease progression. We describe the case of a 49-year-old African American male with a rare presentation of disseminated Kaposi sarcoma as determined by multi-organ work-up. The patient’s cutaneous manifestations involved several hyperpigmented skin lesions, but the worsening of his respiratory symptoms coupled with unexplained weight loss led providers to develop a high suspicion for disseminated disease progression. This case highlights the need to increase awareness of atypical Kaposi sarcoma presentation.