The design of more humane and inclusive automated futures is a wicked design problem. Design disciplines have long addressed wicked problems as socially constructed problems and this chapter explores the critical use of reflective game-playing and generative game-making as a thirdspace approach to produce more socially informed solutions for automated futures. Two cases describing critical tabletop gamemaking for exploring future-oriented ethical issues from two projects are presented: the first case details the design process of a card game created to enable mobility companies to explore how they conceptualise and frame their role as technology innovators in relation to environmental sustainability; the second case details the design process and prototyping of a card game meant to explore privacy issues and the consequences of data sharing behaviours on the internet. Engaging in a co-creative, structured, and reflective process of group prototyping through game-making generates two distinct important learning outcomes that help unravel complex, wicked problems. On one hand, the game-makers directly work to unpack, formalise, and produce an experience that simulates a specific wicked problem, increasing their own awareness and understanding of it. On the other hand, the process produces a concrete artifact in the form of a game that can be later played by unrelated parties ensuring that longer-term knowledge generation can happen. © 2024 Walter de Gruyter GmbH, Berlin/Boston.