Games offer unique possibilities for imagining and experimenting with new systems of governance for more sustainable futures - new rules and institutions, new roles, and new dynamic worlds. However, research on sustainability games has mostly investigated games as a type of futures method, largely divorced from its societal contexts. In this paper, we argue that to unlock the potential of gaming for anticipatory governance in the service of a more sustainable future, it is important take a whole-society perspective, and examine the possibilities and challenges offered by contextual factors. Using the Netherlands and Japan as examples, we investigate the following questions: 1) How do governance cultures allow or restrict opportunities for the participatory exploration of futures using games? 2) How does, and can, the game sector in a given context support anticipatory gaming? 3) How do dominant societal relationships with games limit, and offer opportunities for, gaming for anticipatory governance?