We reviewed the current human immunodeficiency virus (HIV) prevention education programmes in Singapore, discussed the challenges faced and proposed prevention education interventions for the future. Education programmes on HIV prevention have shown some success as seen by reduced visits to sex workers among the general adult population and a marked increase in condom use among brothel-based sex workers. However, we still face many challenges such as low awareness of HIV preventive strategies and high prevalence of HIV stigma in the general population. Voluntary HIV testing and condom use remain low among the priority groups such as men who have sex with men (MSM) and heterosexual men who buy sex. Casual sex has increased markedly from 1.1% in 1989 to 17.4% in 2007 among heterosexuals in Singapore, with the majority (84%) practising unprotected sex. Sex workers have moved from brothels to entertainment venues where sex work is mostly hidden with lack of access to sexually transmitted infections (STIs)/ HIV prevention education and treatment programmes. Education programmes promoting early voluntary testing is hampered because of poor access, high cost and stigma towards people living with HIV. It remains a challenge to promote abstinence and consistent condom use in casual and steady sexual relationships among heterosexuals and MSM. New ways to promote condom use by using a positive appeal about its pleasure enhancing effects rather than the traditional disease-oriented approach should be explored. Education programmes promoting early voluntary testing and acceptance of HIV-infected persons should be scaled up and integrated into the general preventive health services.