This article seeks a deeper understanding of the concept of authentic assessment which ensures it does not become another educational buzzword, slowly diminishing in real meaning. I consider the origins of the term in the US schooling sector, and how it has developed over time, and in different countries, to today focus in higher education largely on real world tasks. There is, however, I argue, a common conflation of real world with the world of work. Little of this literature actually engages with the rich philosophical debates on authenticity, and in this article, I suggest that this deeper understanding of authenticity can enable us to build on existing work on authentic assessment to develop a more holistic and richer concept that will be more beneficial to individual students and to the larger society of which they are part. I argue that we should move from thinking in terms of either the so-called real world, or the world of work, to focus our justification for authentic assessment on its social value (which encompasses but is not limited to its economic value). To achieve this aim, I suggest we move from simply focusing on the authentic task to considering why that task matters? This then enables a shift from the student in isolation to the student as a member of society. Senses of achievement can become richer, thus enhancing the students’ sense of self, self-worth, and well-being.