Effective urban planning is said to be crucial for ensuring liveable, equitable and viable urban areas progress towards sustainability. This study combines a review of the relevant literature, key informant interviews and field observations to explore contemporary planning practices in Dhaka, Bangladesh. We problematize ineffective urban planning practice in Dhaka as a prime expression and reproduction of colonial planning, which manifests itself through institutional bureaucracy and centralization, technocracy, and ad hoc planning. We argue that these imprints have rendered planning institutions weak and fostered dependency on imported ideologies and practices. The situation, we further argue, not only stifles local planning creativity but also makes the planning profession unattractive. Apart from limited local innovations and political aspirations for meeting global development targets, urban planning and city management have followed a reductionist approach under neoliberalism. With little to no social resonance, attempts at creating ordered spaces are, instead, contributing to increased spatial fragmentation and segregation, informality, and widespread urban poverty. To promote urban sustainability, this paper urges the contextualization of colonial ideologies and practices against the social, political and economic realities of urban Bangladesh.