Neisseria (N.) gonorrhea is a gram-negative diplococcus and one of the most commonly reported sexually transmitted infections (STIs) in the United States. Disseminated gonococcal infection is a rare but serious complication of N. gonorrhoeae infection that can result in arthritis-dermatitis syndrome or purulent gonococcal arthritis. Co-infection with human immunodeficiency virus (HIV) has been shown to reduce the efficacy of complement recruitment, which may lead to an increased risk of disseminated gonococcal spread. We present a case of a 41-year-old male with concomitant HIV-gonorrhea infection complicated by rare chronic subacute septic arthritis localized to the left shoulder. The patient had a history of HIV, hypertension, and diabetes, and presented with symptoms, including diarrhea, oral thrush, body aches, and fevers. During his hospitalization, the patient developed increasing left shoulder pain, and imaging and joint aspiration revealed N. gonorrhoeae as the causative agent. The patient was treated with appropriate antibiotics and showed improvement. This case highlights the importance of considering disseminated gonococcal infection as a potential complication of N. gonorrhoeae infection, particularly in patients with concomitant HIV infection, and the need for prompt diagnosis and appropriate treatment to prevent complications.