Chapter 2 uses game adaptations of JRR Tolkien’s The Hobbit (1937) to explore the way that a systems approach to adaptation can alter our understanding of how fidelity, agency, and knowledge operate in the user’s experience of an adaptation. Building on the work of Adam Roberts and folklore scholars, I argue that we can productively read the relationship between Tolkien’s Hobbit and its game adaptations (indeed, any game adaptation and its sources) through the lens of the riddle, a literary form which (like games and adaptations) draws its meaning from the active process of recognition and playful interpretation. With the figure of the riddle in mind, the chapter goes on to analyze a series of Hobbit game adaptations, interrogating how they balance the often-conflicting relationship between the player’s knowledge of the source text and their ability to make meaningful choices as an agent in the storyworld. As I argue in an extended reading of a primary case study—Beam Software’s 1982 text adventure version of The Hobbit—game adaptations can maintain this balance in much the same way that Tolkien did: by integrating dissonances between differing versions of the story as part of the overall experiential system of the text.