This article adopts a principle from game design theory which views “play” as a type of negotiation with (and against) the constraints of a given environment. The performances of The Wasteland Theatre Company, an amateur theater troupe staging Shakespearean texts collaboratively online using the video game Fallout 76, are examined in light of this approach to playing. This article discusses how tensions between the Shakespearean text and the performances of The Wasteland Theatre Company coerce their audiences into active interpretation of both the game’s and the performed text’s content. The principle of playing as negotiation, moreover, has applicability beyond video games. Demonstrating how productions can break or bend the “rules” which their texts or settings impose, The Wasteland Theatre Company’s approach foregrounds the ways in which such rule-breaking encourages audiences to actively interpret the performance.