Communication about sexual health between parents and adolescents has been shown to have a protective influence on behaviours that reduce the risk of HIV transmission. This study explored experiences of HIV and sexual health (HSH) communication between parents and/or caregivers and adolescents in an urban HIV-endemic community in Southern Africa. Adolescents (aged 14–19 years) were recruited from the Kganya Motsha Adolescent Centre and the Kliptown community between June and August 2009. Qualitative data were collected through focus group discussions (n = 10 adolescents) and semi-structured interviews (n = 31 adolescents). In total, 41 adolescents (56% female, 44% male, mean age = 17.2) participated in the study. Adolescent participants identified emotional, physical and sociocultural barriers to initiating HSH communication with parents and caregivers including fear of verbal warnings, threats and physical assault. Adolescents also expressed a desire for mentorship around HSH communication beyond abstinence and peer-based information. Public health interventions need to support adolescents’ access to bi-directional HSH information from adult mentors that address the lived realities of adolescents beyond expectations of abstinence.Keywords: adolescent, parent–adolescent communication, qualitative, sexual health, HIV prevention, South Afric