Khasi is a tribe of the state of Meghalaya, northeast India. It is one of the few communities in India, which is matrilineal, the descent and inheritance being traced in the female line. The children take the mother’s surname, residence is matrilocal—the husband moving into the wife’s house, and the youngest daughter inherits the ancestral property. Matrilineal system among the Khasi has gone a long way in determining the position of Khasi women, who come across as more empowered than women in patrilineal societies. However, moving beyond the general, and taking a closer look at the gender dynamics in the Khasi society at present, one can capture the finer nuances under the overarching matrilineal system, be it the congruent or the paradoxical existence of matriliny and women’s empowerment, the latter encapsulating factors like agency and decision-making and how Khasi women are situated there. The discussion on Khasi matriliny makes it necessary to revisit the relation between the terms—matriliny and matriarchy and the dynamics therein. The chapter explores the emerging voices of angst and protests, the system of inheritance through platforms like Syngkhong Rympei Thymmai (SRT), a men’s rights group raising its demand in favour of patriliny to safeguard Khasi men’s dignity and security. In this line, some existing Acts and proposed Bills demanding alteration in the matrilineal system of inheritance of property among the Khasi have been discussed. For instance, the Khasi Inheritance of Property Bill, 2021, aims at equitable distribution of parental property among siblings (and not only the daughter) in the Khasi society. The article explores the latent tensions experienced by Khasi women as they live in the matrilineal setup and negotiate their lives between the blurred boundaries of privileges and responsibilities that come to them in this system.