The transition toward a sustainable transportation system in the Netherlands takes place in the context of the Dutch “Transition management policy framework”. We study four technological routes that the “Platform Sustainable Mobility” has selected for this goal: (1) hybridization of vehicles, (2) liquid biofuels, (3) natural gas as a transportation fuel and (4) hydrogen as a transportation fuel. These technological routes all envision large-scale changes in vehicle propulsion technology and fuel infrastructure. Furthermore, they compete for the scarce resources available to invest in new (fuel) infrastructures, which implicates that these ‘transition paths’ are also interdependent at the level of the mobility system. The main outcome of the analysis is the identification of barriers that are currently blocking the transition toward sustainable mobility. Barriers are classified as being related to (1) technology and vehicle development, (2) the availability of (fuel) infrastructures, and (3) elements of the institutional infrastructure. The transition management framework currently misses guidelines for coping with (competing) technologies that each require large infrastructural investments. We further argue that avoiding undesired lock-ins and creating a beneficial institutional context for sustainable mobility cannot be pursued at the transition path level. Therefore, we recommend that a more systemic approach should be taken to the transition to sustainablemobility, inwhich the interdependencies between the transition paths are critically assessed and in which the possibilities to legitimize sustainable mobility as a whole should be used.