Syphilis is a sexually transmitted infection with rising incidence in recent years due to increased rates of highrisk sexual behaviors. Often called “the great imitator,” syphilis can have many different presentations in its various stages: latent, primary, secondary and tertiary. One form of secondary syphilis is ulceronodular syphilis, also known as lues maligna. We report a case of a 48-year-old Filipino man who presented with a diffuse, ulcerating, papular rash and was subsequently diagnosed concurrently with both lues maligna and human immunodeficiency virus.