The past 40 years have been characterized by an ongoing shift in the rationale underlying the use of educational technologies -- an earlier emphasis on efficiency and engagement has been overshadowed by a vision centered on educational technologies' capacity to facilitate authentic learning in the inauthentic school context. However, despite its intuitive appeal, authenticity is a vague and contestable concept that warrants further scrutiny. Accordingly, this theoretical paper sets out to offer a conceptual analysis of the various meanings of authenticity in educational discourse, and to examine how these both shape and obfuscate arguments concerning educational technologies. To do so, I identify two key ambiguities inherent in the concept of authenticity: (1) whether authenticity relies on correspondence to real-world contexts ("is"), or aims to tap into a deeper essence of an individual or phenomenon ("ought"); (2) whether authenticity is mainly viewed from a supposedly objective perspective ("external"), or aims to capture individuals' subjective experiences ("internal"). The depiction of technology as authentic, along with the conflations between its various meanings, serve to naturalize existing patterns of technology use, while obscuring the ways in which they are shaped by social, political and pedagogical considerations that should remain open to evaluation and critique.