PURPOSE: To present an atypical case of syphilis that presented with findings concerning for endocarditis and valsalva retinopathy.METHODS: History and clinical examination of 42-year-old white man who presented to the emergency department with acute onset vision changes associated with gastrointestinal symptoms, otalgia, and constitutional symptoms.RESULTS: The review of this case highlights the atypical nature in which syphilis can present and can remain undiagnosed even in the face of extensive workups for other systemic conditions.CONCLUSION: We present a case of syphilis in a patient with multiorgan involvement in whom the diagnosis was made based on atypical ocular examination findings.