The present conceptual literature review analyzes 50 studies that systematically examined the effects of authentic learning settings on cognitive or motivational learning outcomes. The analysis focuses on describing the context of the studies, the design elements of authentic learning settings, and the pursued intentions of authenticity. The review further describes the effects of authentically designed learning settings on cognitive outcomes, motivational outcomes, and learners’ perceived authenticity revealed by previous research. Building on these findings, we conducted Epistemic Network Analysis (ENA) of contrasting cases to identify design elements and intentions of authenticity characterizing studies that show high effectiveness for cognitive and motivational outcomes versus those with low effectiveness. The ENA results suggest, for instance, that providing authentic materials (as a design element of authentic learning settings) to resemble real-life experiences (as an intention of authenticity) could be a double-edged sword, as they feature both authentically designed learning settings with low effects on cognitive outcomes and settings with high effects on motivational outcomes. Overall, the results of the present literature review point to critical limitations of previous research, such as a lack of clear definitions and operationalizations of authentic learning. Consequently, we draw specific conclusions about how future research could improve our understanding of how to create and implement powerful methods of authentic learning.