This chapter examines the emergence of urbanism in Indonesia by comparing two key archaeological sites: Kota Cina in north Sumatra and Trowulan in east Java. Drawing on archaeological data, historical sources, and comparative regional evidence, the chapter argues that urban settlements in Indonesia developed relatively late—beginning around the twelfth to thirteenth centuries—and were shaped not only by political structures but more fundamentally by economic activity, manufacturing specialization, and long-distance trade. Kota Cina represents one of the earliest examples of an economically driven settlement, marked by evidence of craft production, extensive trade networks, and a diverse population. Trowulan, by contrast, demonstrates the characteristics of a mature urban center in the Majapahit period, where new artistic forms, technological innovations, and craft industries flourished alongside religious and political institutions. By tracing how both sites reflect shifting patterns in settlement, economic organization, and cultural expression, this chapter highlights the need to reconsider long-standing assumptions about the nature and timing of early Indonesian urbanism.