Transit-Oriented Development (TOD) is a well-acknowledged strategy to integrate land use and transportation for sustainable urban development. Discourse on TOD characteristically upholds its promise for creation of high-density, compact, and mixed-use developments, supported by public transits to minimise dependence on private vehicles and thus to reduce sprawl, congestion, and pollution. Conversely, several scholars cautioned that the absence of enabling circumstances would turn TODs into Transit Adjacent Developments (TADs), significantly swayed away from the goal of sustainable urban development. Like many other developing nations, India is confronted with a host of urban transportation problems, such as growing use of private vehicles, traffic congestion, degrading urban environment, inequity in allocation of road space between vehicles and pedestrians, increasing road accidents, and such like. The Government of India relies on TOD for ameliorating the present urban transportation problems and, thus, emphasises on public transportation systems for proceeding towards the goal of ‘growth of urban transport along low-carbon path’. This has, lately, resulted in emergence of Rapid Transit Systems (RTS) in several Indian cities, and competent authorities are proceeding towards framing appropriate TOD guidelines. While some of these cities seek to reap the TOD potential accorded by the recent investments in RTS, there are several debates regarding implementation TOD in India. Many of these debates focus on the strategies and potential of land development along transit corridors. Unfortunately, other issues and challenges related to functional connectivity of land use and transit, sustainability, equity, and implementations are less pondered upon. This article aims to identify the issues and challenges for TOD in the context of a developing scenario—in this case Kolkata Metropolitan Area (KMA) in India. The issues are identified, and the need for a multidisciplinary approach for arriving at context-specific and carrying-capacity-based TOD strategies—allowing development along the ‘low-carbon path’—is suggested.