This chapter reports the findings of a study on factors influencing the capacity of planning organizations to break prevailing path dependencies and pave the way for more energy efficient and sustainable transport futures. Empirically, the chapter builds on a qualitative exploration of contemporary land use and transport planning. The planning case in focus illustrates some well-known challenges to establishing sustainable transport and land use development pathways, with specific attention being paid to the dynamics between planning organizations with different roles and mandates, operating at different administrative levels. In the chapter, theories of path dependence are used to discuss ways in which unsustainable and energy-intensive policy pathways are perpetuated, while theories of transformative capacity are used as a framework for exploring what it would take to establish more sustainable transport trajectories. The analysis has led to insights into different types of changes that would enhance the transformative capacity of contemporary land use and transport governance, with a focus on roles, resources and abilities within and across planning organizations, and with attention paid to the wider governance and policy levels. Ultimately however, the chapter concludes that enhanced transformative capacity within and among planning organizations is not enough. What is required is also an active political leadership with a capacity and willingness to engage in the value conflicts that permeate initiatives for sustainable land use and transport transformations.