This paper delves into what the application of authenticity to Human-Machine Communication (HMC) can teach us about authenticity and us as HMC researchers and as a community. Inspired by the 2023 pre-conference “HMC: Authenticity in communicating with machines,” two central questions guide the discussion: How does HMC contribute to our understanding of authentic communication with machines? And how can the concept of authenticity contribute to our sense of self as researchers within the HMC field? Through the collaborative effort of 22 authors, the paper explores the re-conceptualization of authenticity and presents recent areas of tension that guide the HMC research and community. With this paper we aim at offering a gateway for scholars to connect and engage with the evolving HMC field.