This chapter captures the intergenerational anxieties, and the multiple dilemmas the Santal margins experience as they navigate their paradoxical lives in the city. Struggling to construct a ‘nimnomoddhobitto’ meaning lower middle class identity while holding on to their indigenous culture is generating tensions across the generations. While the first-generation Santals are yet to lose their native character, self-perception and cultural integrity despite attaining an urban class identity, the second generation seem to have willingly embraced city life and its influences. City and its transformations grounded in global visions have deepened the impact on their lives and have shaped their world views.