The purpose of this article is to highlight challenges in the relationship between corporate donors and recipient NPOs within the context of corporate social investment (CSI) in South Africa and to link the relational challenges to problems NPOs face in general. It is theoretically argued that CSI forms an important part of sustainable development and that NPOs, in turn, form an integral part of many organisations’ social investment. The challenges faced by them need addressing for the sake of NPOs, donors and society as a whole. It was found that although the stakeholder relationship generally shows both positive and negative perceptions of the parties involved, the challenges that exist can be traced to challenges in the everyday functioning of NPOs, including resource limitations and dependence; staffing problems; and strategy, management and environmental challenges. These challenges facing NPOs manifest in their relationship with donors and can be seen in the power imbalance in the relationship that favours donors, the lack of transparency by NPOs, divergent views on commitment, the questioned competence of NPOs, time constraints in the execution of activities, a perceived incomprehension by NPOs of the realities of the business world, and an unwillingness on the part of donors to allow NPOs some decision-making power.