This paper presents urbanization challenges in India and initiatives taken to address them. Urbanization in India is characterized by skewed urban growth between cities by large population influx creating distinct variation in core and periphery of cities in terms of urban form and services. Key challenges include growth of slums, inadequate management of solid waste, decrease in per capita water availability and unreliable water quality, inadequate sewage coverage and deteriorating ambient air. Although, these issues are not new or specific for India, what is new are the drivers and pressures behind these problems. The paper illustrates the challenges of Indian urbanization in the light of resource inefficiency, resistance to adopt upcoming technologies that do not have direct financial benefits, weak enforcement of laws, and inadequacy in regulatory framework. It also presents instances of active participation of non–formal and formal sectors in addressing sustainability challenges. There is also a recognition of the fact that city governments are faced with multiple sustainability agendas of climate adaptation. This presents a decisional challenge for planners and city administrations. Benefits incidental to a particular policy goal can help drive the implementation of the policy and sustain it in the long term, but only when the inherent risk trade–offs, if present, can be managed.