Urban transport systems are pivotal to economic functionality and social inclusion in rapidly urbanising contexts. This study critically investigates the evolution and current challenges of urban transport in Zimbabwe, with particular emphasis on Harare and Bulawayo, through a qualitative-oriented desk research methodology. Drawing on secondary data sources, the research traces the enduring impact of colonial spatial planning, the retrenchment of state-supported services following the Economic Structural Adjustment Programmes (ESAPs), and the subsequent rise of informal transport systems. The findings of the research which has culminated into this chapter, indicate that colonial-era spatial hierarchies continue to structure urban mobility patterns, reinforcing infrastructure inequalities between low-density and high-density areas. The decline of the Zimbabwe United Passenger Company (ZUPCO), once the backbone of formal public transport, created a vacuum filled by informal modes such as kombis and mushikashika (terms loosely translating to informal, disorganised transport systems) that, while adaptive, remain largely unregulated and contribute to service inefficiencies, congestion, and safety concerns. The research also identifies critical institutional and governance failures, including policy fragmentation, weak local government capacity, and limited investment in non-motorised transport infrastructure. These structural deficiencies exacerbate spatial mismatch, increase commuting costs, and disproportionately burden low-income residents. Despite isolated and disparate efforts to revitalise formal systems, sustainable, integrated, and inclusive urban transport remains elusive. The study concludes that transformative change requires not only technical interventions but also systemic policy reform, inter-agency coordination, and alignment with global frameworks such as the Sustainable Development Goals (SDGs) and the New Urban Agenda. The findings contribute to the discourse on urban transport in the Global South and underscore the necessity of context-sensitive planning paradigms that foreground equity, sustainability, and resilience.