Many cities are dispersed, disconnected and vulnerable to oil price rises. In contemporary urban policy, Transport Orientated Development (TOD) is a popular solution but remains theoretically conflicted and practically expensive. TODs are walkable precincts, centred on train or other public transit systems with dual logistical and place-enhancement functions. The tension of unresolved function is particularly pernicious for marginal TODs. Mindful of the TOD paradox and project pitfalls, we investigate a regeneration project in Brisbane and evaluate the challenges for this site to achieve sustainable urban regeneration. Generalising beyond the Queensland context, we outline possible strategies to overcome challenges to sustainable TOD development. The result suggest that TOD commercial and collective success turns on five key drivers: partnership engagement (informally or in a joint venture), site simplicity, place distinctiveness or sufficient enhancement funding, transport integration, speculative constraints and, finally, authentic local community discourse.