In this dissertation, I examine notions of tradition and fidelity to tradition in Indian classical music by investigating the development of musical judgment, categorical knowledge and aesthetic sense in the performance of Dhrupad - a genre of Hindustani music with medieval origins. Focusing on two contemporary performers of Dhrupad with very different histories of listening and practice, I show that categorical knowledge and strong notions of fidelity to tradition arise directly from the deeply dialogic and inter-subjective processes through which individual musicians develop and stabilize coherent aesthetic response to handed-down musical materials in situated practice. Specifically, I argue that strong notions of tradition and fidelity to tradition in Indian classical music are irreducible to a discussion of the disciplinary technologies of colonialism and cultural nationalism. Rather, I propose that tradition in Indian classical music has to be understood in dialogic relationship with intelligibility and individual musical judgment. I develop an analytical framework to investigate the interactive basis of musical judgment and categorical sense in Dhrupad performance. I understand forms of knowledge produced in performance to be acoustemic: epistemologies produced through active sensing in and through sound. I investigate how formal structures of knowledge in a classical music system become available as human sensibility, affect and soma-aesthetic knowledge in the interactivity of musical environments - an intertwining engendered in part by the affordance of musico-aesthetic forms in Indian classical music. I show that musical objects develop both heterogeneity and ontological weight in the interactivity of Dhrupad vocal performance, rendering performance practice within traditional lineages systematic and heterogeneous, coherent and diverse. Based on this analysis I argue that heterogeneity and diversity are not antithetical to the existence of a Great Tradition of Indian classical music but a part of its sonic logic as a domain of creative human activity. In positing that the categories, codes, classifications and ontologies of the most hoary of genres in Indian classical music are constitutive of and constituted by the situated practice of classical music in particular communities, this dissertation stakes a claim to the intellectual history of traditions in postcolonial contexts.