This roundtable delivers a thought-provoking conversation that engages scholars and performers of South Asian music with the post-Independence history of Indian music in the West and its increasingly complex manifestations (Farrell 2013). This forum aims to cover a gap in the field of study that has, on the one hand, established literature about Western pioneers in the colonial era (Sorrell 2013; Linden 2013; Bor 1996) and, on the other hand, growing research on Indian musics popularized in the West by performers of South Asian origins (Lavezzoli 2007; Slawek 1993; Neuman 1984) including musicians of the second and third diasporas (Ramnaraine 2020; Bakrania 2013; Banerjee 1988). Speaking from their diverse generational, gender, ethnic, and theoretical perspectives, the five presenters and the discussant examine a less investigated aspect: the first wave of Western singers and players who carved their space and professional careers in Hindustani and Karnatik heritage music. Through the case study of postcolonial pioneers such as Jon Higgins (1939-1984), Amelia Cuni (1958-2024), and others who in the last decades of the 20^th century paved the way, this roundtable explores their positionalities outside the lineages of hereditary musicians, as well as their critical contributions to establishing the teaching of Indian music in Western institutions. Presenters debate how, rather than a peripheral phenomenon, these forerunners represent a critical category yet to be recognized, not only for their intercultural efforts as performers and educators but also as custodians of the indigenous knowledge they documented and received from hereditary musicians of a bygone era.