This article aims at providing insight into one of the most important questions that still lurks within the discourses of India’s industrialisation or de-industrialisation. By analysing the case of a particular cotton weaving tradition in India, this article tries to explore how the adoption of new technologies or inflow of capital has brought changes within the labour relationship, which has eventually led to the transition within many other Indian handloom weaving traditions. Other than mere descriptions of structural relationships between stakeholders belonging to different hierarchies of cloth production systems, this article, with its analytic ethnographical framework, focuses on the cultural nuances of the workplace and labour-capital relationships within this particular cotton-weaving tradition. It tries to illuminate how these people get involved, how they interact and engage in different sorts of contracts with one another. Therefore, this article may help in understanding how inequality in the distribution of technical skills and resources instigate the politics of labour relationships, and ultimately how such socio-political arrangements carve the future course of a cloth producing tradition.