Firms face increasing societal pressures to act responsibly towards stakeholders, and community engagement is a key element of this response. While Bowen, Newenham-Kahindi and Herremans (2010) have found that community engagement strategies fall into the transactional, transitional and transformational categories, more research is needed. Nineteen semi-structured interviews were conducted with CSR practitioners, community beneficiaries and external experts across three companies from different sectors and geographically-associated South African communities.Barriers to and enablers of transformational community engagement are identified and compared with points made in the literature. Prominent barriers identified include community expectation; the internal capacity of the company to engage properly with communities; and, according to a new finding in the literature, community educational levels. The most prominent enabler of engagement was relationshipbuilding. Companies with dedicated CSR practitioners are able to engage more in the community. Regulatory dynamics are found to largely determine the differences across sectors. But there is the risk that engagement is symbolic rather than substantive. Eleven higher-order antecedents to transformational community engagement are then identified. A newly developed firm-oriented decision-making model is proposed for moderating these antecedents. The findings in the community and national context provide granular insight into an African operating environment.