A 58-year-old homeless male was brought to emergency department with altered mental status, lethargy, right ear pain, and right ear discharge for the past few days. His past medical history was significant for acquired immunodeficiency syndrome (AIDS) noncompliant with antiretroviral therapy, chronic hepatitis C, chronic kidney disease, and polysubstance abuse especially snorting cocaine. On physical examination, the patient appeared cachectic, in no acute distress. There was tenderness to palpation over the right periauricular area with a visible abscess measured 2 cm  3 cm just anterior to the tragus, grossly visible right nasal perforation measuring 1 cm  1 cm (Figure 1). Ear, nose, and throat evaluation showed right otorrhea, intact right tympanic membrane, opaque, anterior canal wall erythematous with significant prolapse of the right temporomandibular joint (TMJ) into canal, there was pain with palpation of right TMJ, left external auditory canal was occluded by cerumen. The rest of the physical examination was not contributory. An initial noncontrast computed tomography scan of the head showed possible right mastoiditis and TMJ osteomyelitis (OM) (Figure 2). Magnetic resonance imaging of the head without contrast confirmed these findings along with OM involving the mandibular condyle and septic arthritis of the TMJ (Figure 3). Blood and right ear drainage fluid cultures grew methicillin-sensitive Staphylococcus aureus. The patient was placed on intravenous nafcillin 2 gram every 4 hours. Transesophageal echocardiogram did not reveal any vegetation on the cardiac valves. The patient underwent incision and drainage of the right infected TMJ, arthrotomy, and a biopsy of the mandibular right condyle. During the procedure, pus was noted in the right TMJ space, the right condyle was partially eroded, debris was removed and the joint space was thoroughly irrigated. Bone biopsy pathology showed limited fragments of bone with marrow fibrosis and spindle cells without acute inflammation. Bone biopsy culture isolated rare growth of Candida glabrata after 2 weeks thought to be a contaminant.