The chapter endeavours to critically engage with the idea of “progressive cosmopolis” as practised within the modern Assamese public sphere and articulated through the poetry of two influential litterateur–activists—Ambikagiri Raichoudhury and Jyotiprasad Agarwalla. The study undertaken in this chapter will explore the unique features of their respective progressive visions, and how they were represented through their poems and lyrical compositions brought to life in the context of the anti-colonial movement and amidst the complexities that arose in relation to the questions of indigeneity and migration in the years leading to the independence of the country. The study here will engage primarily with a more localised and vernacular vision of progressivism—both as a part of and as a response to its national and cosmopolitan manifestation—which was prevalent in Assam till about the 1940s.