This paper explores the way improvisation served as a symbol of freedom and resistance and as a mediator for transnational artistic exchanges in the wake of 1960s counterculture and civil rights movements. It looks at the way that narratives on freedom and resistance circulated through discourses on improvisation as Indian and jazz musicians in the U.S. and U.K. collaborated to form a new type of improvised music, known as “Indo-jazz fusion,” which combines elements of Indian classical music with jazz and rock. Musicians and scholars typically cite improvisation as the common ground (or mediator) that enabled jazz and Indian classical musicians to interact with one another musically and, more precisely, to create a new genre of music during this period. Indo-jazz makes an interesting case for the study of improvisation because it is rooted in two music traditions, both of which place a heavy emphasis on improvisation as a crucial element of music performance, but which are associated with different understandings of improvisation as an agent of liberation and/ or resistance in social and musical practice. By highlighting the ways that musicians negotiated these conflicting understandings of improvisation in early Indo-jazz musical encounters, this paper raises questions about the persistency of tropes on freedom and resistance in discussions of improvisation today.