Urbanization is often taken to imply a social transformation where upward mobility is experienced by the majority of the urban inhabitants. This is not the case, however, in many urban areas in Indonesia. In Cirebon and Gresik, the modern-capitalist economy continues to develop side by side with burgeoning urban poor communities. Since the construction of asphalt roads more than 200 years ago, the north coast of Java has transformed into an integrated urban corridor of interlinked cities extending from Anyer in the west to Panarukan in the east. The location of important port cities, particularly Batavia (now Jakarta), Cirebon, Semarang, and Surabaya, provides impetus for creating Java’s north coast cities as a major locus of economic growth in the Indonesian archipelago and beyond. Increases in trading, manufacturing, and services, which lure people from the agricultural hinterlands, only absorb a limited number of them into the urban economy, while the majority becomes trapped in the informal economy and low-paid employment. The process of urbanization continues, yet without genuinely improving the social and economic livelihoods of the majority of its citizens. Urbanization as the core process of social transformation has also occurred without clear spatial planning and public participation as the cases of Cirebon and Gresik reveal.