In prison populations around the world, the prevalence of HIV is often higher than that of the general population. The prison population is at high risk for HIV infection, particularly through the sharing of contaminated needles and high-risk sexual activity. Counselling is regarded as a key element in the prevention and treatment of HIV infection. Support groups provide essential supportive counselling for HIV-positive individuals struggling to cope. This paper looks at the challenges to providing a support group for HIV-positive prisoners. The author's experience of attempting to provide a support group highlights two key challenges: organisational issues which lead to disruptions for the group; and challenges to ensuring confidentiality, a core ethical principle in HIV counselling.