For over 30 years, the notion of authentic assessment in higher education has been adopted in academic practice, but it has managed to escape substantial critique. Although there have been multiple definitions and operationalisations of authentic assessment, current practice tends to foreground mimicking of work tasks. Authenticity cannot be completely unmoored from the reality of workplaces, the demands of the discipline, and the overall intended learning outcomes, however, a restricted view of how these aspects are represented in assessment can limit the sector's ability to prepare graduates who can engage with and shape the changing world. This paper elaborates the multiple challenges that some conceptualisations of authentic assessment contribute to assessment planning, recognising that assessment design always requires compromise. Three theoretical perspectives on authenticity are introduced to open new possibilities for authenticity in assessment. These are (1) psychological authenticity; (2) ontological fidelity; and (3) practice theory perspectives. The final section discusses how learning design might offer a means to operationalise theory. The paper concludes by suggesting that "authenticity" in assessment continues to hold value for the sector beyond its current uses through stronger theoretical conceptualisation and operationalisation of authenticity.