Previous studies have identified implementation problems connected to sustainable mobility. These difficulties raise the question of which strategies can be successfully pursued to break path dependencies in urban policy making. This article is focused on corporate mobility management as one specific example of sustainable mobility initiatives, and analyses the formation and implementation of a travel policy for employees at the city administration of Örebro, Sweden. The analysis reveals how controversies can evolve into major implementation barriers for sustainable mobility initiatives. The analysis centres on the playing out of power relations between politicians and groups of officers in the development of interventions to break path dependencies. The strategy pursued in Örebro turned out to be very challenging within the municipality, since it required significant transformation of the officials’ personal travel behaviour, and so led to open conflicts within the city administration. The case demonstrates that radical and confrontational attempts to break path dependencies may result in the same watering down as less controversial, more consensual strategies. When handling controversial sustainable mobility measures there may be more benefit in deliberative strategies of raising awareness, creating new consciousness or institutionalising desired discursive shifts.