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This article draws from a qualitative study of Singapore's gay movement to analyze how gay organizing occurs in authoritarian states, and where and how law matters. Singapore's gay activists engage in “strategic adaptation” to deploy a strategy of pragmatic resistance that involves an interplay among legal restrictions and cultural norms. Balancing the movement's survival with its advancement, they shun direct confrontation, and avoid being seen as a threat to the existing political order. As legal restrictions and as a source of legitimacy, law correspondingly oppresses sexual conduct and civil-political liberties, and culturally delegitimizes dissent. However, when activists mount pragmatic resistance at and through law, it also matters as a source of contestation. Further, law matters as a trade-off between reifying the existing order in exchange for survival and immediate gains. Yet, by treating law as purely tactical, these activists arguably end up de-centering law, being pragmatically unconcerned with whether they are ideologically challenging or being co-opted by it.