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The paper explores the distinct upward mobility journeys of six high-achieving Dalit women in government services in Chennai in south India. Their mobility, primarily driven by education, makes them a ‘select’ group given the larger relatively abysmal social, educational, and occupational inequality of Dalits in India. The paper argues that while collective family resources, combined with affirmative action policies of the state are crucial, the agency displayed by the women was key in facilitating their mobility trajectories. The path of social ascension is strewn with complex economic, emotional, and structural challenges, which required negotiations and, sometimes assertion in order to navigate towards desired goals. Through the women’s narratives on the strategies they employed, the constraints they faced, and the various contexts that shaped their lives, the paper attempts to understand the process of negotiation and assertion in their mobility journeys. The everyday negotiations and assertions the women engaged in were also for enabling broader social goals such as dignity, respectability, and social transformation of the community. This was evident from the women’s strong sense of ‘paying back’ to the community.