Endogenous endophthalmitis (EE) is an ocular infection resulting from hematogenous spread from the remote primary source. Risk factors include endocarditis, bacteria meningitis, immunosuppressive state, and invasive procedures in patients with sepsis. We present a case of a 43-year-old gentleman with poorly controlled diabetes mellitus who was admitted for bilateral nasoseptal cellulitis with a right nasal wall abscess and right vocal cord palsy. At presentation, he just had preseptal cellulitis without any posterior segment involvement. He underwent incision and drainage under the Otorhinolaryngology team. Unfortunately, postoperatively he developed sepsis with a hematogenous spread of infection systemically involving his right eye (endophthalmitis) and his heart valve (infective endocarditis). Blood culture revealed Methicillin Sensitive Staphylococcus Aureus (MSSA) infection. He had six weeks of intravenous cloxacillin and three times intravitreal injections of vancomycin and ceftazidime with complete resolution of signs and symptoms. In the case of a poorly controlled diabetic patient with an extensive regional infection, the presence of ocular symptoms and signs that are suggestive of EE must be taken seriously and warrant a complete eye examination as early detection and treatment of EE is crucial for better prognosis.