The article explores how the unfolding of the Amaravati project in Andhra Pradesh, India, was shaped by the region’s caste-based agrarian social and political formation. It shows how caste structures not only access to land, resources and power, but also the agrarian land transition in the context of a ‘new city’ project. In particular, caste structured the process of land pooling as well as the land market due to the historical embedding of caste in the land governance system. The article outlines two major ways in which caste inequalities and tensions were reproduced and sharpened—the rapid dispossession of Dalits by the unleashing of a speculative land market, and their marginalisation in the land pooling process. These processes are attributed to the institutionalisation of caste within the land revenue bureaucracy and the entrenchment of caste power and ideology within and beyond the state in the Coastal Andhra region, leading to a caste-based ‘land grab’. In response, Dalits mounted opposition to their marginalisation by framing unequal compensation for assigned lands and the alienation of assigned lands as manifestations of caste oppression. The eruption of caste struggles around land in what was supposed to become India’s first ‘fully planned’ city illustrates a key dimension of ‘agrarian urbanisation’ in contemporary India.