ABSTRACT A previously healthy 36-year-old woman was admitted to the hospital with vaginal discharge, bilateral ankle pain, and a lower extremity skin rash, all of which developed after unprotected vaginal intercourse with a new male partner. On examination, there was a petechial and purpuric rash involving the lower extremities and bilateral tenosynovitis of the ankle dorsiflexor tendons. Urine NAAT was positive for Neisseria gonorrhea , confirming disseminated gonococcal infection (DGI). The patient was initially treated with oral azithromycin and intravenous ceftriaxone, but as a result of psychosocial circumstances, she was prematurely discharged on an oral cephalosporin agent. She represented with treatment-failure DGI and was treated with a 7-day course of intramuscular ceftriaxone. Repeat urine NAAT was negative for gonorrhea and the patient remained asymptomatic. This case features an atypical cutaneous manifestation of DGI, characterized by a painless petechial and purpuric skin rash rather than the tender papulo-pustular lesions that are typically seen. Additionally, it highlights the importance of DGI treatment with a 7-day parenteral cephalosporin therapy when antibiotic susceptibility is not available.