The housing dimension in Kolkata has been changing in recent years. Since 1991, the city has initiated housing reform that has taken many forms and manifestations characterized by the reduction in social allocation, cutbacks in public funding, and promotion of a real estate culture in close partnership between the state and private actors. There has been increasing concern about the housing condition of the poor in the deserted slums and bustee settlements amidst the evident ‘poor blindness’ in housing and investment policies. Against this background, the paper discusses self-help housing in Kolkata. It seeks to answer a simple question e why the concept of self-help has not been recognised as a viable policy option for a city with widespread slums and bustee settlements by visiting the complex urban context of Kolkata set within the city’s politics, poverty, and policies. The paper concludes that there is a need to recognize the existing structural duality in the city and support self-help housing as a parallel housing approach.