Sexuality education has become the cornerstone to curbing risky adolescent behaviour as a means to decrease the spread of unsafe sexual practices and prevent the spread of HIV and AIDS. While the implementation thereof has shown effectiveness in practice, the desired change at the community level remains a challenge, especially in relation to multicultural norms and disparities with which educators are faced in different school contexts in Southern Africa. This paper raises the question: How do schools mediate sexuality education in Free State provincial schools to accommodate contextual challenges? In order to investigate how schools mediate uniform national- and curriculum-based benchmarks, 10 participants from five schools within the Free State province were purposefully sampled. Data from semi-structured interviews with participants were coded and themed, with this paper specifically reflecting on the theme of school and community boundaries influencing the implementation of sexuality education. Through a First and Second Order Cybernetic perspective, it was found that challenges of gender and race are among the barriers prohibiting positive feedback within school structures, as well as the need to allow communities and parents to become stakeholders in tailoring sexuality education to be relevant to expected national standards as well as contextual and relevant cultural and traditional values.