We present an atypical case of secondary syphilis concomitant with condyloma lata in an HIV-positive male. The patient presented with lesions on his lateral neck, soles, and palms. Spirochetes were examined on the biopsy of the palm, consistent with secondary syphilis, but not on the biopsy from the neck. The lesion on the neck was diagnosed as an evolving secondary syphilis lesion due to the extent of the lymphoplasmacytic infiltration, presence of acanthosis and epidermal hyperplasia, the accompanying diagnosis of secondary syphilis on the palm, the patient’s history of HIV, and the related diagnosis of condyloma lata on the dorsal shaft of the penis. Following this diagnosis, the patient was referred to an infectious disease specialist who treated him with a single intramuscular injection of 2.4 million units of benzathine penicillin, per CDC guidelines. This case highlights the importance of clinicians taking into consideration a variety of factors when diagnosing and treating cutaneous disorders with a broad-spectrum differential diagnosis, particularly in at-risk individuals.