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Syphilis cases are on the increase especially in men who have sex with men (MSM) in urban areas of high-income countries. There is a strong association between syphilis and HIV infections. We review the more recent literature regarding the epidemiology, clinical manifestations, diagnostic investigations, treatment and follow-up of syphilis in HIV infection. Although the clinical manifestations of syphilis in people living with HIV (PLHIV) and HIV-uninfected patients are broadly similar, differences have been described in PLHIV. Asymptomatic primary syphilis and secondary syphilis are more common in PLHIV as well as several atypical and severe syphilis presentations. Asymptomatic and symptomatic neurosyphilis are also more commonly described in the HIV infected. The use of penicillin regimes remains the mainstay of treatment, although there is evidence of the successful use of non-penicillin-based regimes, e.g. doxycycline. Syphilis infections in PLHIV are common and increasing. A low index of suspicion and testing with appropriate, rapid treatment should decrease the significant morbidity associated with this infection.