This study explores the concept of authenticity in education, which has been, over the last 25 years, a powerful metaphor for educational practice, particularly as a guiding principle for some technological innovations that support student learning. The concept of authenticity has a variety of meanings, although a dominant interpretation is that authenticity refers to the alignment of educational practice with activities in the real world. Based on a meta-analysis of research on the topic, Shaffer and Resnick (1999) proposed unifying the array of meanings for authenticity with their concept of thick authenticity, which included four different aspects of authentic learning: real-world, assessment, disciplinary, and personal authenticity. Thick authenticity synthesizes these different facets into a mutually interdependent whole. This study revisits this discussion two decades later, again conducting a meta-review of recent literature, and re-finding the four meanings for authenticity. However, we also identify in the current literature on authenticity a fifth meaning: teacher authenticity. We then analyze two cases of technology-based teaching to explore how teachers manage the elements of authenticity in their classrooms, what this tells us about the theoretical construct of thick authenticity, and specifically the role that teacher authenticity plays in the orchestration of authentic learning. Based on these short case studies, we argue that teacher authenticity does play a key role in the construction of authentic classroom activities, but that the different elements of authenticity also conflict with and limit one another. As a result, educators need to pay more careful attention to the relationships and contradictions inherent in authentic pedagogy, and balance the different aspects of authenticity rather than focusing on maximizing any one of them. We describe this aligned and coherent understanding of authentic learning as realistic authenticity. Thus, while the primary finding of this study is from the meta-analysis of the literature, the empirical examples illustrate the results of this meta analysis, showing the complexity of authentic learning.