Video games' capacity to facilitate complex and interactive modes of engagement has led to their portrayal as particularly effective means for designing authentic and situated learning environments, which overcome the artificial and abstract nature of conventional teacher-centered schooling. Focusing on the intentional use of progressive-oriented video games (or "serious games") towards educational aims, this paper sets out to go beyond this dichotomy by introducing the "designability paradox of educational video games"--arguing that video games' designed nature both attenuates and accentuates the artificial and abstracted nature of conventional schooling. While video games are more authentic and situated in terms of the modes of participation available to players and intricateness of the simulative environment, they concurrently intensify the artificial and abstracted characteristics of conventional schooling as they represent an increase in the intentional design of learning environments and their separation from external contexts. Based on these analyses, the second part of the paper offers a more nuanced characterization of the types of authenticity and situatedness facilitated by educational video games along two axes: distinguishing between "fictional" and "conceptual" authenticity, and between situatedness that "embeds" or "elicits" learning. This classification is intended to offer a more nuanced understanding of learning in educational video games, and how they should be integrated into educational settings. Accordingly, the paper concludes by identifying three diverging foci of the integration of video games into classrooms: "generalizing" the learning taking place in the game, "formalizing" players' in-game experiences, and "contextualizing" gameplay via critical analysis of the game.