Global Value Chain (GVC) analysis uses the concept of upgrading to highlight paths for developing country firms to “move up the value chain,” usually through the lenses of four categories—product, process, functional, and inter-sectoral upgrading. The implicit normative expectation is that these firms move toward producing higher value-added products and/or take on more sophisticated functions along a value chain. In this article, upgrading is approached more broadly as “reaching a better deal,” including a balance between rewards and risk. The case study of South African wine shows that better product quality, improved processes, and some functional upgrading have co-existed with processes of “downgrading,” higher risks, and limited rewards, especially in traditional export markets. A reflection on further conceptual development and directions for empirical research is also provided.