The clamour for leaders to be authentic in enacting their roles is now widely heard in both the academic literature and popular media. Yet, the authentic leadership (AL) construct remains deeply problematic and arguably impossible to enact. Using the performance of emotional labour (EL) as a lens to view relational transparency, a core component of AL, our research surfaces the paradoxes inherent in this construct and their implications for practicing leaders. Our data reveal something of the mystery surrounding how practicing leaders are able to feel authentic even as they manage their emotions as a routine tool of accomplishing their leadership role. This apparent disconnect between the experiencing of authenticity and the actions/interactions in which this experience is embedded raises profound questions concerning authenticity as a phenomenon, how it is discursively constructed, its relationship to inauthenticity – especially in the practice of leadership – and even its relevance. Drawing on these concerns, we suggest an agenda for future research in relation to authenticity in leadership and highlight the value of EL as a challenging ‘test context’ for honing our understanding of what ‘authenticity’ might mean.