We presented a case of a 55 year old male with history of HTN, alcohol abuse and immunocompromise who presented with rash and fatigue for 3-4 weeks. He describes it as “rough spots” on his scalp and arms which come and go, as well as redness and “pimples” on his chest and back and “dry” skin on his hands and the bottom of his feet. He was seen in the ED 2 months prior for cough and work up was unremarkable. He is sexually active and does not use protection regularly. After excellent physical exam testing for syphilis was sent and he was diagnosed with secondary syphilis. He was given IM benzathine. He developed fevers/chills and myalgias one day later. He recovered well with IV fluid and Tylenol.