Kaposi sarcoma is a low-grade vascular neoplasm linked to the human herpesvirus 8, with the AIDS-associated epidemic variant being the most common and aggressive. Although Kaposi sarcoma more commonly affects the cutaneous tissues, lymph nodes, and visceral organs, it can also be present in ocular and ocular adnexal tissues. We report a case of a 58-year-old Indo-Caribbean woman living with AIDS who presented with a large upper eyelid mass that was clinically diagnosed as Kaposi sarcoma. After the recommencement of the patient's highly active antiretroviral therapy (HAART), the lesion showed marked regression, highlighting the critical role of HAART in the management of Kaposi sarcoma. This is the first documented case of AIDS-associated ocular Kaposi sarcoma in the Eastern Caribbean region and underscores the need to consider Kaposi sarcoma as a differential diagnosis in patients living with HIV/AIDS who present with ocular or ocular adnexal masses.