This dissertation investigates the intersection between urban change and the shifting social, cultural, and political dynamics in late Ottoman and Mandate Palestine. Against standard historiography that reads the history of cities and urban change under imperial and colonial rule from the perspective of dominating powers, this dissertation emphasises the role of the local Palestinian population in conceiving, planning, and shaping their urban environments and spaces within, against, and parallel to the exigencies of imperialism and colonialism. It is primarily a history of the colonised rather than the coloniser. Through a relational historical study of the experiences of the two cities of Jaffa and Nablus, the dissertation probes into the uneven yet interlinked trajectories of Palestine’s urban transformation. It treats the two cities not as more or less modern than one another but as constitutive of a multifaceted process of modernisation that encompassed relations of interdependence and rivalry between cities and within them. To do this, the dissertation draws on spatial and architectural analysis coupled with extensive archival research. In treating the spatiality and materiality of urban environments as the main lens to read historical urban processes and dynamics, it contributes to emerging critical scholarship in architectural and urban studies, imperial and colonial histories, and area studies. The dissertation is structured around four interrelated themes, comprising its main vehicles for interpreting urban change: inter-urban relations, urban industries, urban governance, and urban public life. It shows how these elements contributed to the continuities that characterised Palestine’s transition from Ottoman to British rule, challenging the idea of a rupture between the two historical periods. It further demonstrates how, more than a mere setting for other dynamics, the city had turned into a primary interest throughout the late nineteenth and early twentieth centuries, inviting overlapping and contradictory visions for the future of urban Palestine.