This article reflects on contestations that mark queer and trans community building in post- National Legal Services Authority (NALSA) and post-377 India. In the past decade, queer and trans communities in India have witnessed two landmark judgements: the NALSA v. Union of India judgement 2014 and the Navtej Singh Johar and Ors. v. Union of India judgement 2018. The former granted transgender persons legal recognition and a promise of civil and substantive rights. The latter read down the draconian Sec. 377 of the Indian Penal Code that criminalized consensual adult homosexual sex acts. In light of these two judgements, this article traces challenges faced by queer and trans communities and challenges to queer and trans community building in contemporary India by tracing recent developments in the contexts of health, public policy, jurisprudence, social institutions, education, popular culture, and the precarity of gender and sexually transgressive communities during the recent COVID-19 pandemic. Finally, the authors also trace narratives of hope that demonstrate how queer and trans people in post legal reform India continue to build enabling and affirmative communities in the face of an increasingly neoliberalizing country.