Despite advances in clinical care, safer conception services are not utilised in many high HIV prevalence countries, including Botswana. We conducted in-depth interviews with 10 HIV healthcare providers and 10 women living with HIV to develop a deeper understanding of attitudes surrounding childbearing and pregnancy planning. Interviews were analysed using a phenomenological approach. Providers felt it was a human right and normative for women living with HIV to have children but also expressed concern about women living with HIV having children. Women themselves anticipated stigma from providers regarding childbearing, although most described supportive care and had not experienced stigmatising treatment. Although providers believed pregnancies amongst women living with HIV were unplanned, women described discussing pregnancy desires with sexual partners. Despite providers voicing a rights-based approach to childbearing amongst women living with HIV, hesitancy towards pregnancy remains. This is felt by women living with HIV and perceived as stigma, which may make them less likely to seek fertility and safer conception advice. Safer conception interventions are unlikely to be successful if women do not feel comfortable discussing childbearing with health-care providers.